2,2'-methylenebis[(4R,5R)-4-methyl-5-phenyl-2-oxazoline] | 132098-55-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2'-methylenebis[(4R,5R)-4-methyl-5-phenyl-2-oxazoline]
• 英文别名: (4R,5R)-4-methyl-2-[[(4R,5R)-4-methyl-5-phenyl-4,5-dihydro-1,3-oxazol-2-yl]methyl]-5-phenyl-4,5-dihydro-1,3-oxazole
• CAS: 132098-55-6
• 化学式: C₂₁H₂₂N₂O₂
• 分子量: 334.418
• InChiKey: ULXXRDSOVACWDK-RPQNVMPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  L-(-)-去甲伪麻黄碱 、 丙二酸二乙酯 在 二甲基溴化锡 作用下， 生成 2,2'-methylenebis[(4R,5R)-4-methyl-5-phenyl-2-oxazoline]
  参考文献：
  名称：

  四环[7.3.1.0 2,8 .0 4,12 ] trideca-5,10-二烯的简并Cope重排

  摘要：

  四环[7.3.1.0 2,8 0.0 4,12 ]十三-5,10-二烯（3）合成的和部分经由可逆配体交换解决在其4 η二烯tfacac -铑（I）配合物10和11与C 2-手性双齿双-[[4（R）-甲基-5（R）-苯基恶唑啉基]甲烷]阴离子。在39 – 57°C之间测量（+）3的Cope重排，将其转换成其镜像。动力学参数表明，这种重排的速率比母体hexa-1,5-二烯的重排速率快10 8倍。保持架混合物3的应变和刚度提供一个解释。©1997爱思唯尔科学有限公司。

  DOI：

  10.1016/s0040-4020(97)00335-9

文献信息

• Asymmetric catalytic cyclopropanation of olefins: bis-oxazoline copper complexes
  作者：Richard E Lowenthal、Atsushi Abiko、Satoru Masamune

  DOI：10.1016/s0040-4039(00)98014-6

  日期：1990.1

  Bis-oxazolines (1–7) prepared from diethyl malonate and chiral amino alcohols were converted into their Cu(II) complexes which, upon activation, exhibit high enantioselectivity of up to 99 %ee for catalytic cyclopropanation of olefins.

  由丙二酸二乙酯和手性氨基醇制得的双恶唑啉（1–7）被转化为它们的Cu（II）配合物，该配合物在活化后对烯烃的催化环丙烷化表现出高达99％ee的高对映选择性。
• 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。
• 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。
• US6858559B2
  申请人：——

  公开号：US6858559B2

  公开（公告）日：2005-02-22
• [EN] NOVEL PROCESSES FOR THE PREPARATION OF PHENYLCYCLOPROPYLAMINE DERIVATIVES AND USE THEREOF FOR PREPARING TICAGRELOR<br/>[FR] NOUVEAUX PROCÉDÉS POUR LA PRÉPARATION DE DÉRIVÉS DE PHÉNYLCYCLOPROPYLAMINE ET LEUR UTILISATION POUR LA PRÉPARATION DE TICAGRELOR
  申请人：ACTAVIS GROUP PTC EHF

  公开号：WO2012001531A2

  公开（公告）日：2012-01-05

  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.