Title:
ホスホノクロトン酸誘導体の製造方法
Document Type and Number:
Japanese Patent JP5925767
Kind Code:
B2
Abstract:
Provided is a method of manufacturing a high quality phosphonocrotonic acid derivative. The present invention is a method of manufacturing a compound represented by the following Formula (3) by reacting a compound represented by the following Formula (1) with a compound represented by the following Formula (2), which comprises a treatment process using an acid or base. [in the formula, R 1 represents a C 1-6 linear or branched alkyl group that may be substituted by a C 6-10 aryl group, a C 2-6 linear or branched alkenyl group that may be substituted by a C 6-10 aryl group, a C 2-6 linear or branched alkynyl group that may be substituted by a C 6-10 aryl group, or a C 6-10 aryl group, R 2 represents a hydrogen atom, or a C 1-6 linear or branched alkyl group that may be substituted by a C 6-10 aryl group, R 3 represents a C 1-6 linear or branched alkyl group, a C 6-10 aryl group, or a halogen atom, and X represents a halogen atom, and multiple R 1 s may be the same or different].
Inventors:
Masatsugu Ina
Takahiro Yamazaki
Junichi Sakata
Koji Esaki
Katsuhiro Sakamoto
Takahiro Yamazaki
Junichi Sakata
Koji Esaki
Katsuhiro Sakamoto
Application Number:
JP2013512421A
Publication Date:
May 25, 2016
Filing Date:
April 26, 2012
Export Citation:
Assignee:
Kowa Co., Ltd.
Manac Inc.
Manac Inc.
International Classes:
C07F9/40; C07C51/09; C07C51/353; C07C57/03; C07C57/26; C07C67/343; C07C69/587; C07C69/734
Domestic Patent References:
| JP2001002621A | 2001-01-09 | |||
| JP2004331654A | 2004-11-25 | |||
| JPH07118225A | 1995-05-09 |
Other References:
JPN6015051140; Ｉｑｃａｌ， Ｍ． ｅｔ ａｌ．: 'Ｓｙｎｔｈｅｓｉｓ ｏｆ １３Ｃ ｓｉｎｇｌｅ ａｎｄ ｄｏｕｂｌｅ ｌａｂｅｌｌｅｄ ｒｅｔｉｎａｌｓ， ｐｒｅｃｕｒｓｏｒｓ ｆｏｒ ＮＭＲ ｓｔｕｄｉｅｓ ｏｆ ｖｉｓｕａｌ ｐｉｇｍｅｎｔｓ' Ｊｏｕｒｎａｌ ｏｆ Ｌａｂｅｌｌｅｄ Ｃｏｍｐｏｕｎｄｓ ａｎｄ Ｒａｄｉｏｐｈａｒｍａｃｅｕｔｉｃａｌｓ ｖｏｌ．２２ ｎｏ．８, 1985, ｐｐ．８０７-８１７
JPN6015051144; Ｓａｆａｒｙｎ， Ｊ． Ｅ． ｅｔ ａｌ．: 'Ａ ｃｏｎｖｅｎｉｅｎｔ ｓｙｎｔｈｅｓｉｓ ｏｆ （±）-ａｓｃｏｃｈｌｏｒｉｎ' Ｔｅｔｒａｈｅｄｒｏｎ ｖｏｌ．４２ ｎｏ．１０, 1986, ｐｐ．２６３５-２６４２
JPN6015051146; Ｐｏｍｍｅｒ， Ｈｏｒｓｔ: 'Ｓｙｎｔｈｅｓｅｓ ｉｎ ｔｈｅ ｖｉｔａｍｉｎ Ａ ｓｅｒｉｅｓ' Ａｎｇｅｗａｎｄｔｅ Ｃｈｅｍｉｅ ｖｏｌ．７２ ｎｏ．２２, 1960, ｐｐ．８１１-８１９
JPN6015051148; Ｄｕａｎ， Ｚｈｅｎｇ-Ｃｈａｏ ｅｔ ａｌ．: 'Ｅｎａｎｔｉｏｓｅｌｅｃｔｉｖｅ Ｒｈ-ｃａｔａｌｙｚｅｄ ｈｙｄｒｏｇｅｎａｔｉｏｎ ｏｆ ３-ａｒｙｌ-４-ｐｈｏｓｐｈｏｎｏｂｕｔｅｎｏａｔｅｓ ｗｉｔｈ ａ ｐ-ｓｔｅｒｅｏｇｅｎｉｃ ＢｏＰ' Ｊｏｕｒｎａｌ ｏｆ Ｏｒｇａｎｉｃ Ｃｈｅｍｉｓｔｒｙ ｖｏｌ．７５ ｎｏ．２３, 2010, ｐｐ．８３１９-８３２１
JPN6015051151; Ｃｈｉｅｆａｒｉ， Ｊｏｈｎ ｅｔ ａｌ．: 'Ｔｈｅ ｓｙｎｔｈｅｓｉｓ ｏｆ ｐｈｏｓｐｈｏｎｏｂａｃｌｏｆｅｎ， ａｎ ａｎｔａｇｏｎｉｓｔ ｏｆ ｂａｃｌｏｆｅｎ' Ａｕｓｔｒａｌｉａｎ Ｊｏｕｒｎａｌ ｏｆ Ｃｈｅｍｉｓｔｒｙ ｖｏｌ．４０ ｎｏ．９, 1987, ｐｐ．１５１１-１５１８
JPN6015051153; Ｄｕｃ， Ｌａｕｒｅｎｔ ｅｔ ａｌ．: 'Ｍｅｔｈｙｌ （Ｅ）-４-ｃｈｌｏｒｏ-３-ｍｅｔｈｏｘｙ-２-ｂｕｔｅｎｏａｔｅ： Ａｎ ｅｘｔｒｅｍｅｌｙ ｖｅｒｓａｔｉｌｅ ｆｏｕｒ ｃａｒｂｏｎ ｂｕｉｌｄｉｎｇ ｂｌｏｃｋ' Ｓｙｎｔｈｅｓｉｓ ｎｏ．４, 1992, ｐｐ．３９１-３９４
JPN6015051134; Ｍａｔａ， Ｅｒｎｅｓｔｏ Ｇ． ｅｔ ａｌ．: 'Ｄｅｖｅｌｏｐｍｅｎｔ ｏｆ ａ ｓｙｎｔｈｅｓｉｓ ｏｆ ｌａｎｋａｃｉｄｉｎｓ： ａｎ ｉｎｖｅｓｔｉｇａｔｉｏｎ ｉｎｔｏ １７-ｍｅｍｂｅｒｅｄ ｒｉｎｇ ｆｏｒｍａｔｉｏｎ' Ｊｏｕｒｎａｌ ｏｆ ｔｈｅ Ｃｈｅｍｉｃａｌ Ｓｏｃｉｅｔｙ， Ｐｅｒｋｉｎ Ｔｒａｎｓａｃｔｉｏｎｓ １ ｎｏ．７, 1995, ｐｐ．７８５-７９９
JPN6015051137; Ｍａｇｏｕｌａｓ， Ｇｅｏｒｇｅ Ｅ． ｅｔ ａｌ．: 'Ｓｙｎｔｈｅｓｅｓ， ａｎｔｉｐｒｏｌｉｆｅｒａｔｉｖｅ ａｃｔｉｖｉｔｙ ａｎｄ ｔｈｅｏｒｅｔｉｃａｌ ｃｈａｒａｃｔｅｒｉｚａｔｉｏｎ ｏｆ ａｃｉｔｒｅｔｉｎ-ｔｙｐｅ ｒｅｔｉｎｏｉｄｓ ｗ' Ｅｕｒｏｐｅａｎ Ｊｏｕｒｎａｌ ｏｆ Ｍｅｄｉｃｉｎａｌ Ｃｈｅｍｉｓｔｒｙ ｖｏｌ．４６ ｎｏ．２, 20101214, ｐｐ．７２１-７３７
JPN6015051140; Ｉｑｃａｌ， Ｍ． ｅｔ ａｌ．: 'Ｓｙｎｔｈｅｓｉｓ ｏｆ １３Ｃ ｓｉｎｇｌｅ ａｎｄ ｄｏｕｂｌｅ ｌａｂｅｌｌｅｄ ｒｅｔｉｎａｌｓ， ｐｒｅｃｕｒｓｏｒｓ ｆｏｒ ＮＭＲ ｓｔｕｄｉｅｓ ｏｆ ｖｉｓｕａｌ ｐｉｇｍｅｎｔｓ' Ｊｏｕｒｎａｌ ｏｆ Ｌａｂｅｌｌｅｄ Ｃｏｍｐｏｕｎｄｓ ａｎｄ Ｒａｄｉｏｐｈａｒｍａｃｅｕｔｉｃａｌｓ ｖｏｌ．２２ ｎｏ．８, 1985, ｐｐ．８０７-８１７
JPN6015051144; Ｓａｆａｒｙｎ， Ｊ． Ｅ． ｅｔ ａｌ．: 'Ａ ｃｏｎｖｅｎｉｅｎｔ ｓｙｎｔｈｅｓｉｓ ｏｆ （±）-ａｓｃｏｃｈｌｏｒｉｎ' Ｔｅｔｒａｈｅｄｒｏｎ ｖｏｌ．４２ ｎｏ．１０, 1986, ｐｐ．２６３５-２６４２
JPN6015051146; Ｐｏｍｍｅｒ， Ｈｏｒｓｔ: 'Ｓｙｎｔｈｅｓｅｓ ｉｎ ｔｈｅ ｖｉｔａｍｉｎ Ａ ｓｅｒｉｅｓ' Ａｎｇｅｗａｎｄｔｅ Ｃｈｅｍｉｅ ｖｏｌ．７２ ｎｏ．２２, 1960, ｐｐ．８１１-８１９
JPN6015051148; Ｄｕａｎ， Ｚｈｅｎｇ-Ｃｈａｏ ｅｔ ａｌ．: 'Ｅｎａｎｔｉｏｓｅｌｅｃｔｉｖｅ Ｒｈ-ｃａｔａｌｙｚｅｄ ｈｙｄｒｏｇｅｎａｔｉｏｎ ｏｆ ３-ａｒｙｌ-４-ｐｈｏｓｐｈｏｎｏｂｕｔｅｎｏａｔｅｓ ｗｉｔｈ ａ ｐ-ｓｔｅｒｅｏｇｅｎｉｃ ＢｏＰ' Ｊｏｕｒｎａｌ ｏｆ Ｏｒｇａｎｉｃ Ｃｈｅｍｉｓｔｒｙ ｖｏｌ．７５ ｎｏ．２３, 2010, ｐｐ．８３１９-８３２１
JPN6015051151; Ｃｈｉｅｆａｒｉ， Ｊｏｈｎ ｅｔ ａｌ．: 'Ｔｈｅ ｓｙｎｔｈｅｓｉｓ ｏｆ ｐｈｏｓｐｈｏｎｏｂａｃｌｏｆｅｎ， ａｎ ａｎｔａｇｏｎｉｓｔ ｏｆ ｂａｃｌｏｆｅｎ' Ａｕｓｔｒａｌｉａｎ Ｊｏｕｒｎａｌ ｏｆ Ｃｈｅｍｉｓｔｒｙ ｖｏｌ．４０ ｎｏ．９, 1987, ｐｐ．１５１１-１５１８
JPN6015051153; Ｄｕｃ， Ｌａｕｒｅｎｔ ｅｔ ａｌ．: 'Ｍｅｔｈｙｌ （Ｅ）-４-ｃｈｌｏｒｏ-３-ｍｅｔｈｏｘｙ-２-ｂｕｔｅｎｏａｔｅ： Ａｎ ｅｘｔｒｅｍｅｌｙ ｖｅｒｓａｔｉｌｅ ｆｏｕｒ ｃａｒｂｏｎ ｂｕｉｌｄｉｎｇ ｂｌｏｃｋ' Ｓｙｎｔｈｅｓｉｓ ｎｏ．４, 1992, ｐｐ．３９１-３９４
JPN6015051144; Ｓａｆａｒｙｎ， Ｊ． Ｅ． ｅｔ ａｌ．: 'Ａ ｃｏｎｖｅｎｉｅｎｔ ｓｙｎｔｈｅｓｉｓ ｏｆ （±）-ａｓｃｏｃｈｌｏｒｉｎ' Ｔｅｔｒａｈｅｄｒｏｎ ｖｏｌ．４２ ｎｏ．１０, 1986, ｐｐ．２６３５-２６４２
JPN6015051146; Ｐｏｍｍｅｒ， Ｈｏｒｓｔ: 'Ｓｙｎｔｈｅｓｅｓ ｉｎ ｔｈｅ ｖｉｔａｍｉｎ Ａ ｓｅｒｉｅｓ' Ａｎｇｅｗａｎｄｔｅ Ｃｈｅｍｉｅ ｖｏｌ．７２ ｎｏ．２２, 1960, ｐｐ．８１１-８１９
JPN6015051148; Ｄｕａｎ， Ｚｈｅｎｇ-Ｃｈａｏ ｅｔ ａｌ．: 'Ｅｎａｎｔｉｏｓｅｌｅｃｔｉｖｅ Ｒｈ-ｃａｔａｌｙｚｅｄ ｈｙｄｒｏｇｅｎａｔｉｏｎ ｏｆ ３-ａｒｙｌ-４-ｐｈｏｓｐｈｏｎｏｂｕｔｅｎｏａｔｅｓ ｗｉｔｈ ａ ｐ-ｓｔｅｒｅｏｇｅｎｉｃ ＢｏＰ' Ｊｏｕｒｎａｌ ｏｆ Ｏｒｇａｎｉｃ Ｃｈｅｍｉｓｔｒｙ ｖｏｌ．７５ ｎｏ．２３, 2010, ｐｐ．８３１９-８３２１
JPN6015051151; Ｃｈｉｅｆａｒｉ， Ｊｏｈｎ ｅｔ ａｌ．: 'Ｔｈｅ ｓｙｎｔｈｅｓｉｓ ｏｆ ｐｈｏｓｐｈｏｎｏｂａｃｌｏｆｅｎ， ａｎ ａｎｔａｇｏｎｉｓｔ ｏｆ ｂａｃｌｏｆｅｎ' Ａｕｓｔｒａｌｉａｎ Ｊｏｕｒｎａｌ ｏｆ Ｃｈｅｍｉｓｔｒｙ ｖｏｌ．４０ ｎｏ．９, 1987, ｐｐ．１５１１-１５１８
JPN6015051153; Ｄｕｃ， Ｌａｕｒｅｎｔ ｅｔ ａｌ．: 'Ｍｅｔｈｙｌ （Ｅ）-４-ｃｈｌｏｒｏ-３-ｍｅｔｈｏｘｙ-２-ｂｕｔｅｎｏａｔｅ： Ａｎ ｅｘｔｒｅｍｅｌｙ ｖｅｒｓａｔｉｌｅ ｆｏｕｒ ｃａｒｂｏｎ ｂｕｉｌｄｉｎｇ ｂｌｏｃｋ' Ｓｙｎｔｈｅｓｉｓ ｎｏ．４, 1992, ｐｐ．３９１-３９４
JPN6015051134; Ｍａｔａ， Ｅｒｎｅｓｔｏ Ｇ． ｅｔ ａｌ．: 'Ｄｅｖｅｌｏｐｍｅｎｔ ｏｆ ａ ｓｙｎｔｈｅｓｉｓ ｏｆ ｌａｎｋａｃｉｄｉｎｓ： ａｎ ｉｎｖｅｓｔｉｇａｔｉｏｎ ｉｎｔｏ １７-ｍｅｍｂｅｒｅｄ ｒｉｎｇ ｆｏｒｍａｔｉｏｎ' Ｊｏｕｒｎａｌ ｏｆ ｔｈｅ Ｃｈｅｍｉｃａｌ Ｓｏｃｉｅｔｙ， Ｐｅｒｋｉｎ Ｔｒａｎｓａｃｔｉｏｎｓ １ ｎｏ．７, 1995, ｐｐ．７８５-７９９
JPN6015051137; Ｍａｇｏｕｌａｓ， Ｇｅｏｒｇｅ Ｅ． ｅｔ ａｌ．: 'Ｓｙｎｔｈｅｓｅｓ， ａｎｔｉｐｒｏｌｉｆｅｒａｔｉｖｅ ａｃｔｉｖｉｔｙ ａｎｄ ｔｈｅｏｒｅｔｉｃａｌ ｃｈａｒａｃｔｅｒｉｚａｔｉｏｎ ｏｆ ａｃｉｔｒｅｔｉｎ-ｔｙｐｅ ｒｅｔｉｎｏｉｄｓ ｗ' Ｅｕｒｏｐｅａｎ Ｊｏｕｒｎａｌ ｏｆ Ｍｅｄｉｃｉｎａｌ Ｃｈｅｍｉｓｔｒｙ ｖｏｌ．４６ ｎｏ．２, 20101214, ｐｐ．７２１-７３７
JPN6015051140; Ｉｑｃａｌ， Ｍ． ｅｔ ａｌ．: 'Ｓｙｎｔｈｅｓｉｓ ｏｆ １３Ｃ ｓｉｎｇｌｅ ａｎｄ ｄｏｕｂｌｅ ｌａｂｅｌｌｅｄ ｒｅｔｉｎａｌｓ， ｐｒｅｃｕｒｓｏｒｓ ｆｏｒ ＮＭＲ ｓｔｕｄｉｅｓ ｏｆ ｖｉｓｕａｌ ｐｉｇｍｅｎｔｓ' Ｊｏｕｒｎａｌ ｏｆ Ｌａｂｅｌｌｅｄ Ｃｏｍｐｏｕｎｄｓ ａｎｄ Ｒａｄｉｏｐｈａｒｍａｃｅｕｔｉｃａｌｓ ｖｏｌ．２２ ｎｏ．８, 1985, ｐｐ．８０７-８１７
JPN6015051144; Ｓａｆａｒｙｎ， Ｊ． Ｅ． ｅｔ ａｌ．: 'Ａ ｃｏｎｖｅｎｉｅｎｔ ｓｙｎｔｈｅｓｉｓ ｏｆ （±）-ａｓｃｏｃｈｌｏｒｉｎ' Ｔｅｔｒａｈｅｄｒｏｎ ｖｏｌ．４２ ｎｏ．１０, 1986, ｐｐ．２６３５-２６４２
JPN6015051146; Ｐｏｍｍｅｒ， Ｈｏｒｓｔ: 'Ｓｙｎｔｈｅｓｅｓ ｉｎ ｔｈｅ ｖｉｔａｍｉｎ Ａ ｓｅｒｉｅｓ' Ａｎｇｅｗａｎｄｔｅ Ｃｈｅｍｉｅ ｖｏｌ．７２ ｎｏ．２２, 1960, ｐｐ．８１１-８１９
JPN6015051148; Ｄｕａｎ， Ｚｈｅｎｇ-Ｃｈａｏ ｅｔ ａｌ．: 'Ｅｎａｎｔｉｏｓｅｌｅｃｔｉｖｅ Ｒｈ-ｃａｔａｌｙｚｅｄ ｈｙｄｒｏｇｅｎａｔｉｏｎ ｏｆ ３-ａｒｙｌ-４-ｐｈｏｓｐｈｏｎｏｂｕｔｅｎｏａｔｅｓ ｗｉｔｈ ａ ｐ-ｓｔｅｒｅｏｇｅｎｉｃ ＢｏＰ' Ｊｏｕｒｎａｌ ｏｆ Ｏｒｇａｎｉｃ Ｃｈｅｍｉｓｔｒｙ ｖｏｌ．７５ ｎｏ．２３, 2010, ｐｐ．８３１９-８３２１
JPN6015051151; Ｃｈｉｅｆａｒｉ， Ｊｏｈｎ ｅｔ ａｌ．: 'Ｔｈｅ ｓｙｎｔｈｅｓｉｓ ｏｆ ｐｈｏｓｐｈｏｎｏｂａｃｌｏｆｅｎ， ａｎ ａｎｔａｇｏｎｉｓｔ ｏｆ ｂａｃｌｏｆｅｎ' Ａｕｓｔｒａｌｉａｎ Ｊｏｕｒｎａｌ ｏｆ Ｃｈｅｍｉｓｔｒｙ ｖｏｌ．４０ ｎｏ．９, 1987, ｐｐ．１５１１-１５１８
JPN6015051153; Ｄｕｃ， Ｌａｕｒｅｎｔ ｅｔ ａｌ．: 'Ｍｅｔｈｙｌ （Ｅ）-４-ｃｈｌｏｒｏ-３-ｍｅｔｈｏｘｙ-２-ｂｕｔｅｎｏａｔｅ： Ａｎ ｅｘｔｒｅｍｅｌｙ ｖｅｒｓａｔｉｌｅ ｆｏｕｒ ｃａｒｂｏｎ ｂｕｉｌｄｉｎｇ ｂｌｏｃｋ' Ｓｙｎｔｈｅｓｉｓ ｎｏ．４, 1992, ｐｐ．３９１-３９４
Attorney, Agent or Firm:
Alga Patent Office, a patent business corporation
Toshio Takano
Toshio Nakajima
Masaki Murata
Hiroto Yamamoto
Toshio Takano
Toshio Nakajima
Masaki Murata
Hiroto Yamamoto