1,3-dibenzyl-2-oxo-imidazolidine-4,5-dicarboxylic acid anhydride | 40222-70-6

• 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: 1,3-dibenzyl-2-oxo-imidazolidine-4,5-dicarboxylic acid anhydride
• 英文别名: 1,3-dibenzyl-tetrahydro-furo[3,4-d]imidazole-2,4,6-trione；4,6-bisbenzyl-2,4,6,3a,6a-pentahydro-4,6-diaza-2-oxapentalen-1,3,5-trione；4,6-bisbenzyl-2,4-6-3a,6a-pentahydro-4,6-diaza-2-oxapentalen-1,3,5-trione；cis-1,3-dibenzyl-hexahydro-1H-furo[3,4-d]imidazole-2,4,6-trione；cis-1,3-dibenzylhexahydro-1H-furo[3,4-d]imidazole-2,4,6-trione；1,3-Dibenzyldihydro-1h-furo[3,4-d]imidazole-2,4,6(3h)-trione；1,3-dibenzyl-3a,6a-dihydrofuro[3,4-d]imidazole-2,4,6-trione
• CAS: 40222-70-6
• 化学式: C₁₉H₁₆N₂O₄
• 分子量: 336.347
• InChiKey: WIVKAHXCBJSNDF-UHFFFAOYSA-N

物化性质

• 沸点：
  597.3±50.0 °C(Predicted)
• 密度：
  1.388±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-dibenzyl-2-oxo-imidazolidine-4,5-dicarboxylic acid anhydride 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 C₇₅H₁₀₄O₆P₂ 、 氢气 作用下， 以 四氢呋喃 为溶剂， 70.0 ℃ 、8.0 MPa 条件下， 反应 18.0h， 以95%的产率得到
  参考文献：
  名称：

  [EN] A NEW CHIRAL BIPHENYL DIPHOSPHINE LIGAND AND PROCESS FOR PREPARATION THEREOF
  [FR] NOUVEAU LIGAND DE DIPHOSPHINE DE BIPHÉNYLE CHIRAL ET SON PROCÉDÉ DE PRÉPARATION

  摘要：

  本发明涉及一种新的手性联苯二膦配体，其化学式为(I)，其中R1、R2和R3分别为H、烷基或芳基；R6和R7分别为取代基；A为芳基或杂环芳基，可以选择性地被一个或多个取代基取代，或其立体异构体，或其立体异构混合物。

  公开号：

  WO2018189107A1
• 作为产物：
  描述：

  环酸 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 13.0h， 以90%的产率得到1,3-dibenzyl-2-oxo-imidazolidine-4,5-dicarboxylic acid anhydride
  参考文献：
  名称：

  WO2008/71696

  摘要：

  公开号：

文献信息

• Process for producing optically active hemiesters
  申请人：——

  公开号：US20010023302A1

  公开（公告）日：2001-09-20

  There is disclosed a process for producing an optically active hemiester of formula (1): 1 wherein R 1 , R 2 and R 5 represent the same meanings as described below, which comprises reacting a cyclic acid anhydride of formula (2): 2 wherein R 1 and R 2 are different and independently represent a hydrogen atom, a halogen atom, an alkyl group optionally substituted with an alkoxy group or a halogen atom, and the like, with a hydroxy compound of formula (3): R 3 OH   (3) wherein R 3 represents an alkyl group optionally substituted with an alkoxy group, a phenoxy group, a dialkylamino group or a halogen atom and the like, in the presence of an asymmetric catalyst.

  揭示了一种生产式（1）的光学活性半酯的过程：其中R1，R2和R5代表如下所述的相同含义，包括将式（2）的环酸酐与式（3）的羟基化合物在不对称催化剂存在下反应，其中R1和R2分别代表氢原子、卤素原子、可能用烷氧基或卤素原子取代的烷基基团等，R3代表可能用烷氧基、苯氧基、二烷基胺基或卤素原子取代的烷基基团等。
• Cinchona-alkaloid-based catalysts, and asymmetric alcoholysis of cyclic anhydrides using them
  申请人：Deng Li

  公开号：US20050043353A1

  公开（公告）日：2005-02-24

  One aspect of the present invention relates to cinchona-alkaloid-based catalysts. A second aspect of the invention relates to a method of preparing a derivatized cinchona alkaloid catalyst by reacting a cinchona-alkaloid with base and a compound that has a suitable leaving group. Another aspect of the present invention relates to a method of preparing a chiral, non-racemic compound from a prochiral cyclic anhydride or a meso cyclic anhydride, comprising the step of: reacting a prochiral cyclic anhydride or a meso cyclic anhydride with a nucleophile in the presence of a catalyst; wherein said prochiral cyclic anhydride or meso cyclic anhydride comprises an internal plane of symmetry or point of symmetry or both; thereby producing a chiral, non-racemic compound; wherein said catalyst is a derivatized cinchona-alkaloid. Yet another aspect of the present invention relates to a method of kinetic resolution, comprising the step of: reacting a racemic cyclic anhydride with an alcohol in the presence of a derivatized cinchona-alkaloid catalyst.

  本发明的一个方面涉及基于金鸡纳碱的催化剂。本发明的第二个方面涉及通过将金鸡纳碱与碱和具有适当离去基团的化合物反应来制备衍生金鸡纳碱催化剂的方法。本发明的另一个方面涉及从一个前手循环酸酐或一个中间循环酸酐制备手性非拉克米化合物的方法，包括以下步骤：在催化剂的存在下，将前手循环酸酐或中间循环酸酐与亲核试剂反应；其中所述前手循环酸酐或中间循环酸酐包括一个内部对称平面或对称点或两者；从而产生手性非拉克米化合物；其中所述催化剂是衍生金鸡纳碱。本发明的另一个方面涉及一个动力学分辨的方法，包括以下步骤：在衍生金鸡纳碱催化剂的存在下，将拉克米循环酸酐与醇反应。
• Monoesters of imidazolidinone dicarboxylic acids
  申请人：Hoffmann-La Roche Inc.

  公开号：US04687859A1

  公开（公告）日：1987-08-18

  A novel process for the manufacture of the optically active lactone of the formula ##STR1## is described.

  描述了一种用于制造式的光学活性内酯的新工艺。
• Process for preparing biotin
  申请人：F. Hoffmann-La Roche AG

  公开号：US20010020101A1

  公开（公告）日：2001-09-06

  The present invention is directed to a process for the production of 2-oxo-1,3-dibenzyl-cis-4,5-imidazolidinedicarboxylic acid and of 2-oxo-1,3-dibenzyl-cis-4,5-imidazolidinedicarboxylic acid anhydride, starting from meso-2,3-bis(benzylamino)succinic acid dialkali metal salt. The process involves reacting meso-2,3-bis(benzylamino)succinic acid dialkali metal salt with phenyl chloroformate in a monophasic solvent system consisting of an about 2:1 to 1:1 mixture of a water-miscible ether and an aqueous alkali metal hydroxide solution, at a temperature not exceeding about 40° C. The resulting 2-oxo-1,3-dibenzyl-cis-4,5-imidazolidinedicarboxylic acid dialkali metal salt is converted, by acidification, into the desired 2-oxo-1,3-dibenzyl-cis-4,5-imidazolidinedicarboxylic acid, which is then either isolated, or converted, by heating with acetic anhydride, in an aromatic hydrocarbon as the organic solvent, into the desired 2-oxo-1,3-dibenzyl-cis-4,5-imidazolidinedicarboxylic acid anhydride, which is in turn, isolated. Each product is an important intermediate in the multi-stage process for the manufacture of biotin (vitamin H).

  本发明涉及一种从中性2,3-双(苄氨基)琥珀酸二碱金属盐出发制备2-氧代-1,3-双苄基-顺式-4,5-咪唑烷二羧酸和2-氧代-1,3-双苄基-顺式-4,5-咪唑烷二羧酸酐的工艺。该工艺包括将中性2,3-双(苄氨基)琥珀酸二碱金属盐与苯基氯甲酸酯在单相溶剂体系中反应，所述单相溶剂体系由水溶性醚和含有碱金属氢氧化物的水溶液的约2:1至1:1混合物组成，反应温度不超过约40°C。生成的2-氧代-1,3-双苄基-顺式-4,5-咪唑烷二羧酸二碱金属盐通过酸化转化为所需的2-氧代-1,3-双苄基-顺式-4,5-咪唑烷二羧酸，然后可以将其分离或者通过与乙酸酐在芳香烃作为有机溶剂的条件下加热转化为所需的2-氧代-1,3-双苄基-顺式-4,5-咪唑烷二羧酸酐，然后将其分离。每种产品都是生产生物素（维生素H）的多阶段过程中的重要中间体。
• 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。