(4S,5R)-1,3-dibenzyl-5-(n-propoxycarbonyl)-2-oxo-imidazolidine-4-carboxylic acid | 83889-76-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4S,5R)-1,3-dibenzyl-5-(n-propoxycarbonyl)-2-oxo-imidazolidine-4-carboxylic acid
• 英文别名: (4S,5R)-1,3-Dibenzyl-5-n-propyloxycarbonyl-2-oxoimidazolidine-4-carboxylic acid；(4S,5R)-1,3-dibenzyl-5-(n-propoxycarbonyl)-2-oxoimidazolidine-4-carboxylic acid；(4S,5R)-1,3-dibenzyl-5-n-propoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid；(4S,5R)-1,3-dibenzyl-2-oxo-5-propoxycarbonylimidazolidine-4-carboxylic acid
• CAS: 83889-76-3
• 化学式: C₂₂H₂₄N₂O₅
• 分子量: 396.443
• InChiKey: NFQQKLXLAFETNH-RBUKOAKNSA-N

物化性质

• 熔点：
  78-82 °C
• 沸点：
  604.7±55.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  87.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S,5R)-1,3-dibenzyl-5-(n-propoxycarbonyl)-2-oxo-imidazolidine-4-carboxylic acid 在 锂硼氢 作用下， 生成 (3aS,6aR)-1,3-二苄基四氢-1H-呋喃并[3,4-d]咪唑-2,4-二酮 、 (3aR,6aS)-1,3-dibenzyltetrahydro-1H-furo[3,4-d]imidazole-2,4-dione
  参考文献：
  名称：

  Iriuchijima, Shinobu; Hasegawa, Keiko; Tsuchihashi, Gen-ichi, Agricultural and Biological Chemistry, 1982, vol. 46, # 7, p. 1907 - 1910

  摘要：

  DOI：
• 作为产物：
  描述：

  cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid 在 氯化亚砜 、 phosphate buffer 作用下， 以 丙酮 为溶剂， 反应 25.5h， 生成 (4S,5R)-1,3-dibenzyl-5-(n-propoxycarbonyl)-2-oxo-imidazolidine-4-carboxylic acid
  参考文献：
  名称：

  Iriuchijima, Shinobu; Hasegawa, Keiko; Tsuchihashi, Gen-ichi, Agricultural and Biological Chemistry, 1982, vol. 46, # 7, p. 1907 - 1910

  摘要：

  DOI：

文献信息

• Intermediates to optically active
  申请人：Sumitomo Chemical Company, Limited

  公开号：US04496739A1

  公开（公告）日：1985-01-29

  A process for preparing an optically active cis-1,3-dibenzylhexahydro-1H-furo[3,4-d]imidazole-2,4-dione of the formula: ##STR1## wherein an asterisk (*) indicates an asymmetric carbon, Bzl represents a benzyl group and the 3a- and 6a-positions take the cis-configuration, which comprises reducing selectively an optically active cis-imidazolidinedicarboxylic acid monoester of the formula: ##STR2## wherein R is a C.sub.1 -C.sub.6 alkyl group and Bzl is as defined above with a reducing agent at either one of the carboxyl group and the alkoxycarbonyl group in the said monoester, followed by cyclization, the said monoester being the one obtainable by hydrolysis of a cis-imidazolidinedicarboxylic acid diester of the formula: ##STR3## wherein R and Bzl are each as defined above with an enzymatic material having a capability of hydrolyzing the ester group in the said diester.

  一种制备光学活性的顺式-1,3-二苯基六氢-1H-呋喃[3,4-d]咪唑-2,4-二酮的方法，其化学式为：##STR1## 其中星号(*)表示手性碳，Bzl代表苯甲基，3a-和6a-位置采取顺式构型，包括选择性还原式顺式咪唑烷二羧酸单酯的方法，其化学式为：##STR2## 其中R是C.sub.1-C.sub.6烷基，Bzl如上所定义，使用还原剂在该单酯的羧基和烷氧基羰基之一上进行还原，然后进行环化，所述单酯是通过酶材料水解式顺式咪唑烷二羧酸二酯得到的，其化学式为：##STR3## 其中R和Bzl如上所定义，该酶材料具有水解所述二酯中的酯基的能力。
• Preparation of optically active
  申请人：Sumitomo Chemical Co., Ltd.

  公开号：US04544635A1

  公开（公告）日：1985-10-01

  A process for preparing an optically active cis-1,3-dibenzylhexahydro-1H-furo[3,4-d]imidazole-2,4-dione of the formula: ##STR1## wherein an asterisk (*) indicates an asymmetric carbon, Bzl represents a benzyl group and the 3a- and 6a-positions take the cis-configuration, which comprises reducing selectively an optically active cis-imidazolidinedicarboxylic acid monoester of the formula: ##STR2## wherein R is a C.sub.1 -C.sub.6 alkyl group and Bzl is as defined above with a reducing agent at either one of the carboxyl group and the alkoxycarbonyl group in the said monoester, followed by cyclization.

  一种制备光学活性的cis-1,3-二苯甲基六氢-1H-呋喃[3,4-d]咪唑-2,4-二酮的方法，其化学式为：##STR1## 其中星号(*)表示不对称碳，Bzl表示苄基，3a-和6a-位置采用顺式构型，该方法包括选择性还原化学式为：##STR2## 的光学活性顺式-咪唑烷二羧酸单酯，其中R为C1-C6烷基，Bzl如上所定义，用还原剂在该单酯的羧基团或烷氧基羰基团中的任一一个进行还原，然后进行环化。
• Preparation of optically active cis-1,3-dibenzyl-hexahydro-1H-furo(3,4-d)imidazole-2,4-dione and its intermediates
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0084892A2

  公开（公告）日：1983-08-03

  A process for preparing an optically active cis-1,3-diben- zylhexahydro-1 H-furo[3,4-d]imidazole-2,4-dione of the formula: wherein an asterisk (*) indicates an asymmetric carbon, Bzl represents a benzyl group and the 3a- und 6a-positions take the cis-configuration, which comprises reducing selectively an optically acitve cis-imidazolidinedicarboxylic acid monoester of the formula: wherein R is a C1-C6 alkyl group and Bzl is as defined above with a reducing agent at either one of the carboxyl group and the alkoxycarbonyl group in the said monoester, followed by cyclization, the said monoester being that obtainable by hydrolysis of a cis-imidazolidinedicarboxylic acid diester of the formula: wherein R and Bzl are each as defined above with an enzymatic material capable of hydrolyzing the ester group in the said diester.

  一种制备光学活性顺式-1,3-二苄六氢-1 H-呋喃并[3,4-d]咪唑-2,4-二酮的工艺，其式如下 其中星号(*)表示不对称碳，Bzl表示苄基，3a-和6a-位为顺式构型，包括选择性还原式中的光学活性顺式咪唑烷二羧酸单酯： 其中 R 为 C1-C6 烷基，Bzl 如上定义，在上述单酯中的羧基和烷氧羰基中的任一基团上用还原剂还原，然后环化，上述单酯是通过水解式如下的顺式咪唑烷二羧酸二酯得到的： 其中 R 和 Bzl 分别如上文所定义，使用一种能水解上述二酯中酯基的酶材料。
• Method of obtaining optically active half esters
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0092194A1

  公开（公告）日：1983-10-26

  A method of separating optically active half esters comprising optically resolving a mixture of a (4S,5R)-1,3-dibenzyl-5-alkoxy or alkenyloxycarbonyl-2-oxoimidazolidine-4-carboxylic acid and a (4R,5S)-1,3-dibenzyl-5-alkoxy or alkenyloxycarbonyl-2-oxoimidazolidine-4-carboxylic acid, each being represented by the formula (I): wherein R1 is an alkyl group or an alkenyl group, each having 1 to 5 carbon atoms; Bzl is a benzyl group; * indicates an asymmetric carbon atom; and the 4- and 5-positions are a cis-configuration, using an optically active d- or 1-amine represented by the formula (II): wherein R2 and R3 are each a hydrogen atom, a halogen atom or methyl group; and indicates an asymmetric carbon atom; and the eforementioned half esters are disclosed. A method for the preparation of an optically active (4S,5R)-cis-1,3-dibenzyl-5-methoxy- or ethoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid (la') or (4R,5S)-cis-1,3-dibenzyl-5-methoxy- or ethoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid (Ib'), comprising preferentially crystallizing (Ia') or (Ib') from a supersaturated solution where (la' ) and (Ib') are copresent in the presence of crystals of the same type of optically active half ester as that to be crystallized, is also disclosed.

  一种分离光学活性半酯的方法，包括光学解析(4S,5R)-1,3-二苄基-5-烷氧基或烯酰氧基羰基-2-氧代咪唑烷-4-羧酸和(4R,5S)-1,3-二苄基-5-烷氧基或烯酰氧基羰基-2-氧代咪唑烷-4-羧酸的混合物，各自由式(I)表示： 其中 R1 是烷基或烯基，各具有 1 至 5 个碳原子；Bzl 是苄基；* 表示不对称碳原子；4 位和 5 位为顺式构型，使用由式（II）表示的具有光学活性的 d- 或 1-胺： 其中 R2 和 R3 各为氢原子、卤素原子或甲基；且表示不对称碳原子；本发明公开了上述半酯。一种制备光学活性(4S,5R)-顺式-1,3-二苄基-5-甲氧基-或乙氧基羰基-2-氧代咪唑烷-4-羧酸(la')或(4R,5S)-顺式-1,3-二苄基-5-甲氧基-或乙氧基羰基-2-氧代咪唑烷-4-羧酸(Ib')的方法、本发明还公开了(Ia')或(Ib')从过饱和溶液中优先结晶的方法，其中(la')和(Ib')在与待结晶的光学活性半酯类型相同的晶体存在下共存。
• A method for preparing optically active half esters
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0220435A1

  公开（公告）日：1987-05-06

  A method for the preparation of an optically active (4S,5R)-cis-1,3-dibenzyl-5-methoxy- or ethoxycarbonyl-2- oxoimidazolidine-4-carboxylic acid (Ia') or (4R,5S)-cis-1,3-dibenzyl-5-methoxy- or ethoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid (Ib'), comprising preferentially crystallizing (la') or (Ib') from a supersaturated solution where (Ia') and Ib') are copresent in the presence of crystals of the same type of optically active half ester as that to be crystallized is disclosed.

  一种制备光学活性(4S,5R)-顺式-1,3-二苄基-5-甲氧基-或乙氧基羰基-2-氧代咪唑烷-4-羧酸(Ia')或(4R,5S)-顺式-1,3-二苄基-5-甲氧基-或乙氧基羰基-2-氧代咪唑烷-4-羧酸(Ib')的方法、本发明公开了(Ia')和(Ib')共存的过饱和溶液中(la')或(Ib')的结晶方法，该方法包括在与待结晶的光学活性半酯类型相同的晶体存在下，优先从该溶液中结晶出(la')或(Ib')。