(4R,5S)-1,3-dibenzyl-5-(methoxycarbonyl)-2-oxo-imidazolidine-4-carboxylic acid | 87637-48-7

• 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: (4R,5S)-1,3-dibenzyl-5-(methoxycarbonyl)-2-oxo-imidazolidine-4-carboxylic acid
• 英文别名: (4R,5S)-1,3-Dibenzyl-5-(methoxycarbonyl)-2-oxoimidazolidine-4-carboxylic acid；1,3-dibenzyl-5-(methoxycarbonyl)-2-oxoimidazolidine-4-carboxylic acid；(4R,5S)-cis-1,3-dibenzyl-5-methoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid；(4R,5S)-1,3-dibenzyl-5-methoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid
• CAS: 87637-48-7
• 化学式: C₂₀H₂₀N₂O₅
• 分子量: 368.389
• InChiKey: BSWUHWZVMBPALP-SJORKVTESA-N

物化性质

• 沸点：
  590.6±50.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (4R,5S)-1,3-dibenzyl-5-(methoxycarbonyl)-2-oxo-imidazolidine-4-carboxylic acid 生成 (3aR,6aS)-1,3-dibenzyltetrahydro-1H-furo[3,4-d]imidazole-2,4-dione
  参考文献：
  名称：

  OHASHI, NAOHITO;SHIMAGO, KOZO;IKEDA, TAKAHARU;ISHIZUMI, KIKUO

  摘要：

  DOI：
• 作为产物：
  描述：

  cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid 在 3-(3,5-bis(trifluoromethyl)phenylamino)-4-((1R,2R)-1-(4-nitrophenyl)-2-(pyrrolidin-1-yl)-3-(trityloxy)propylamino)cyclobut-3-ene-1,2-dione 作用下， 以 甲基叔丁基醚 、 甲苯 为溶剂， 反应 21.0h， 生成 (4R,5S)-1,3-dibenzyl-5-(methoxycarbonyl)-2-oxo-imidazolidine-4-carboxylic acid
  参考文献：
  名称：

  Ding, Liang-Qian; Hong, Dan-Feng; Liu, Wen-Guang, Indian Journal of Heterocyclic Chemistry, 2018, vol. 28, # 3, p. 429 - 432

  摘要：

  DOI：

文献信息

• Catalytic asymmetric desymmetrization of prochiral and meso compounds
  申请人：——

  公开号：US20040082809A1

  公开（公告）日：2004-04-29

  The present invention relates to methods for the synthesis of chiral non-racemic products, e.g., enantiomerically-enriched hemiesters, from prochiral and meso starting materials, e.g., prochiral and meso cyclic anhydrides. The present invention also relates to catalysts for the aforementioned methods, and methods for synthesizing these catalysts.

  本发明涉及从非对映体和中性起始物质，例如非对映富集的半酯，合成手性非拉式产物的方法，例如非对映富集的半酯，从非手性和中性环状酸酐起始物质，例如非手性和中性环状酸酐。本发明还涉及上述方法的催化剂，以及合成这些催化剂的方法。
• A family of novel bifunctional organocatalysts: Highly enantioselective alcoholysis of meso cyclic anhydrides and its application for synthesis of the key intermediate of P2X7 receptor antagonists
  作者：Hong-Jun Yang、Fang-Jun Xiong、Jie Li、Fen-Er Chen

  DOI：10.1016/j.cclet.2013.04.009

  日期：2013.7

  Abstract A family of novel squaramides/sulfamides based on 1,2-alkamine was developed as chiral bifunctional catalysts to promote the asymmetric alcoholysis of meso cyclic anhydrides. The hemiesters were obtained in high yield with up to 93% ee. The usefulness of this methodology was demonstrated in the asymmetric synthesis of the key intermediate of P2X7 receptor antagonists.

  摘要研制了一系列以1,2-链胺为基础的新型方酸/亚磺酰胺作为手性双官能催化剂，以促进内消旋环酸酐的不对称醇解。半酯以高达93％ee的高收率获得。P2X7受体拮抗剂关键中间体的不对称合成证明了该方法的有效性。
• A Formal Catalytic Asymmetric Synthesis of (+)-Biotin with Modified Cinchona Alkaloids
  作者：Chulho Choi、Shi-Kai Tian、Li Deng

  DOI：10.1055/s-2001-16748

  日期：——

  A formal catalytic asymmetric synthesis of (+)-biotin was realized. The key steps involve a catalytic, highly enantioselec- tive and quantitative desymmetrization of a meso cyclic anhydride followed by a one-pot chemoselective reduction to form the optical- ly active lactone intermediate in the Goldberg-Sternbach (+)-biotin synthesis.

  实现了(+)-生物素的正式催化不对称合成。关键步骤涉及内消旋环酐的催化、高度对映选择性和定量去对称化，然后是一锅化学选择性还原，在 Goldberg-Sternbach (+)-生物素合成中形成光学活性内酯中间体。
• 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。