2,2'-methylenebis[(4R)-4-phenyl-5,5-diphenyl-2-oxazoline] | 220578-26-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2,2'-methylenebis[(4R)-4-phenyl-5,5-diphenyl-2-oxazoline]
• 英文别名: 2,2'-methylenebis[(4R)-4-phenyl-5,5-diphenyloxazoline]；2,2'-methylenebis[4(R)-phenyl-5,5-diphenyloxazoline]；Bis((R)-4,5,5-triphenyl-4,5-dihydrooxazol-2-yl)methane；(4R)-4,5,5-triphenyl-2-[[(4R)-4,5,5-triphenyl-4H-1,3-oxazol-2-yl]methyl]-4H-1,3-oxazole
• CAS: 220578-26-7
• 化学式: C₄₃H₃₄N₂O₂
• 分子量: 610.755
• InChiKey: DGJGXEILSKRHNG-GYOJGHLZSA-N

物化性质

• 沸点：
  693.3±55.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  47
• 可旋转键数：
  8
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-甲苯磺酰氰 、 2,2'-methylenebis[(4R)-4-phenyl-5,5-diphenyl-2-oxazoline] 在 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-2-((R)-4,5,5-triphenyl-4,5-dihydrooxazol-2-yl)-2-((R)-4,5,5-triphenyloxazolidin-2-ylidene)acetonitrile
  参考文献：
  名称：

  镍催化芳基氯和芳基溴与醛的对映选择性羰基加成

  摘要：

  以氰基双(恶唑啉)为手性配体，Mn为还原剂，研究了镍催化芳基卤化物与醛的对映选择性加成反应。芳基溴和杂芳基溴与苯醛反应生成二苄醇，产率 16-99%，ee 53-92%。此外，苯氯与芳基、杂芳基和烷基醛可以高产率合成具有中等对映选择性的二苄醇。

  DOI：

  10.1002/chem.202401591
• 作为产物：
  描述：

  D-苯甘氨酸甲酯盐酸盐 在 magnesium 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 2,2'-methylenebis[(4R)-4-phenyl-5,5-diphenyl-2-oxazoline]
  参考文献：
  名称：

  镍催化芳基氯和芳基溴与醛的对映选择性羰基加成

  摘要：

  以氰基双(恶唑啉)为手性配体，Mn为还原剂，研究了镍催化芳基卤化物与醛的对映选择性加成反应。芳基溴和杂芳基溴与苯醛反应生成二苄醇，产率 16-99%，ee 53-92%。此外，苯氯与芳基、杂芳基和烷基醛可以高产率合成具有中等对映选择性的二苄醇。

  DOI：

  10.1002/chem.202401591

文献信息

• NOVEL PROCESSES FOR THE PREPARATION OF PHENYLCYCLOPROPYLAMINE DERIVATIVES AND USE THEREOF FOR PREPARING TICAGRELOR
  申请人：Khile Anil Shahaji

  公开号：US20130165696A1

  公开（公告）日：2013-06-27

  Provided herein are novel processes for the preparation of phenylcyclopropylamine derivatives, which are useful intermediates in the preparation of triazolo[4,5-d]pyrimidine compounds. Provided particularly herein are novel, commercially viable and industrially advantageous processes for the preparation of a substantially pure ticagrelor intermediate, trans-(1R,2S)-2-(3,4-difluorophenyl)-cyclopropylamine. Provided further herein are novel acid addition salts of trans-(1R,2S)-2-(3,4-difluorophenyl)-cyclopropylamine, and process for their preparation. The intermediate and its acid addition salts are useful for preparing ticagrelor, or a pharmaceutically acceptable salt thereof, in high yield and purity.

  本文提供了一种制备苯基环丙胺衍生物的新型工艺，这些衍生物在三唑并[4,5-d]嘧啶化合物的制备中是有用的中间体。特别提供了一种新颖、商业可行且在工业上具有优势的工艺，用于制备一种基本纯的替卡格雷中间体，即trans-(1R,2S)-2-(3,4-二氟苯基)-环丙胺。此外，本文还提供了trans-(1R,2S)-2-(3,4-二氟苯基)-环丙胺的新型酸加盐，以及其制备工艺。该中间体及其酸加盐对于高产率和纯度制备替卡格雷或其药用可接受盐是有用的。
• Optically active bisoxazoline compounds, production and use thereof
  申请人：Sumitomo Chemical Company, Limited

  公开号：US06072081A1

  公开（公告）日：2000-06-06

  An optically active bisoxazoline compound of the formula [I]: ##STR1## wherein R.sub.1 represents alkyl group, cycloalkyl group, aralkyl group, phenyl group which may be substituted or alkoxy group and two geminal alkyl groups may be joined together to form a cyclic structure; R.sub.2 represents alkyl group, cycloalkyl group, aralkyl group, phenyl group which may be substituted; R.sub.3 represents hydrogen atom, (C2-C4)alkyl group or cycloalkyl group; and the asterisk * represents an asymmetric carbon atom.

  化学式[I]的光学活性双噁唑啉化合物：其中R₁代表烷基，环烷基，芳基，苯基（可能被取代）或烷氧基，两个伪生烷基可能结合形成环状结构；R₂代表烷基，环烷基，芳基，苯基（可能被取代）；R₃代表氢原子，（C2-C4）烷基或环烷基；星号*代表一个不对称的碳原子。
• Asymmetric copper complex and cyclopropanation reaction using the same
  申请人：——

  公开号：US20020177718A1

  公开（公告）日：2002-11-28

  There are disclosed asymmetric copper complex comprising, as components, (a) an optically active bisoxazoline compound of formula (1): 1 wherein R 1 and R 2 are different and each represent a hydrogen atom, an alkyl group, a cycloalkyl group, or a phenyl or aralkyl group which may be substituted, R 3 and R 4 each represent a hydrogen atom, an alkyl group, a cycloalkyl group, or a phenyl or aralkyl group which may be substituted, or R 3 and R 4 may be bonded to each other to form a C 3-5 cyclic alkylene group, R 5 represents a hydrogen atom or a C 1-6 alkyl group, or the two R 5 groups may be bonded to each other to represent a C 3-5 cyclic alkylene group, (b) a monovalent or divalent copper compound, and (c) a strong acid or a Lewis acid or a mixture thereof, and a process for producing an optically active cyclopropanecarboxylate using the same.

  揭示了包括以下组分的不对称铜络合物：（a）公式（1）的手性双噁唑啉化合物：其中R1和R2不同，每个代表氢原子、烷基、环烷基、苯基或芳基烷基，可能被取代，R3和R4每个代表氢原子、烷基、环烷基、苯基或芳基烷基，可能被取代，或者R3和R4可以相互连接形成C3-5环烷基，R5代表氢原子或C1-6烷基，或者两个R5基团可以相互连接形成C3-5环烷基；（b）一价或二价铜化合物；和（c）强酸或Lewis酸或二者混合物，以及使用它们制备手性环丙烷羧酸酯的方法。
• Method for producing optically active chrysanthemic acid
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20020123645A1

  公开（公告）日：2002-09-05

  Disclosed is a method for producing an optically active chrysanthemic acid, which method is characterized by optical resolution of a chrysanthemic acid having a trans isomer ratio of not less than 70% and an optical purity of 2% e.e. to less than 10% e.e. with an optically active organic.

  公开了一种生产光学活性菊酯酸的方法，该方法的特征是利用光学活性有机物对具有不低于70%的顺式异构体比率和2% e.e.至少10% e.e.的光学纯度的菊酯酸进行光学分辨。
• Copper complexes of optically active bisoxazolines as enantioselective catalysts in cyclopropanation reactions
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP0895992A2

  公开（公告）日：1999-02-10

  An optically active bisoxazoline compound of the formula [I]: wherein R1 represents an alkyl group, cycloalkyl group, aralkyl group, phenyl group which may be substituted or an alkoxy group and two geminal alkyl groups may be joined together to form a cyclic structure;    R2 represents an alkyl group , cycloalkyl group, aralkyl group or phenyl group which may be substituted;    R3 represents a hydrogen atom, (C2-C4)alkyl group or cycloalkyl group; and    the asterisk * represents an asymmetric carbon atom.

  式[I]的光学活性双噁唑啉化合物： 其中 R1 代表烷基、环烷基、芳基、可被取代的苯基或烷氧基，两个烷基可连接在一起形成环状结构； R2 代表烷基、环烷基、芳基或可被取代的苯基； R3 代表氢原子、(C2-C4)烷基或环烷基；以及 星号 * 代表不对称碳原子。