(3R,4S)-methyl 3-phenyl-4-(4-(trifluoromethyl)phenyl)cyclohepta-1,5-dienecarboxylate | 1345876-81-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (3R,4S)-methyl 3-phenyl-4-(4-(trifluoromethyl)phenyl)cyclohepta-1,5-dienecarboxylate
• 英文别名: methyl (3R,4S)-3-phenyl-4-[4-(trifluoromethyl)phenyl]cyclohepta-1,5-diene-1-carboxylate
• CAS: 1345876-81-4
• 化学式: C₂₂H₁₉F₃O₂
• 分子量: 372.387
• InChiKey: BBDBKDAGJBCNLM-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (E)-methyl 2-diazo-4-phenylbut-3-enoate 、 (E)-1-(buta-1,3-dien-1-yl)-4-(trifluoromethyl)benzene 在 dirhodium tetrakis((R)-1-(4-bromophenyl)-2,2-diphenylcyclopropanecarboxylate) 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到(3R,4S)-methyl 3-phenyl-4-(4-(trifluoromethyl)phenyl)cyclohepta-1,5-dienecarboxylate
  参考文献：
  名称：

  D₂-Symmetric Dirhodium Catalyst Derived from a 1,2,2-Triarylcyclopropanecarboxylate Ligand: Design, Synthesis and Application

  摘要：

  Dirhodium tetrakis-(R)-(1-(4-bromophenyl)-2,2-diphenylcyclopropanecarboxylate) (Rh-2(R-BTPCP)(4)) was found to be an effective chiral catalyst for enantioselective reactions of aryl- and styryldiazoacetates. Highly enantioselective cyclopropanations, tandem cyclopropanation/Cope rearrangements and a combined C- functionalization/Cope rearrangement were achieved using Rh-2(R-BTPCP)(4) as catalyst. The advantages of Rh-2(R-BTPCP)(4) include its ease of synthesis, its tolerance to the size of the ester group in the styryldiazoacetates, and its compatibility with clichloromethane as solvent. Computational studies suggest that the catalyst adopts a D-2-symmetric arrangement, but when the carbenoid binds to the catalyst, two of the p-bromophenyl groups on the ligands rotate outward to make room for the carbenoid and the approach of the substrate to the carbenoid.

  DOI：

  10.1021/ja2074104

文献信息

• DIRHODIUM CATALYST COMPOSITIONS AND SYNTHETIC PROCESSES RELATED THERETO
  申请人：EMORY UNIVERSITY

  公开号：US20140155643A1

  公开（公告）日：2014-06-05

  This disclosure relates to compositions comprising dirhodium catalysts and uses related thereto, e.g., in enantioselective transformations of donor/acceptor carbenoids. In certain embodiments, the dirhodium catalyst comprises a cyclopropyl ring substituted with a carboxylic acid ligand. In certain embodiments, the disclosure relates to compositions comprising a compound of the following formula, or salts thereof wherein, R 1 , R 2 , and R 3 are defined herein.

  这项披露涉及包含二铑催化剂的组合物及其相关用途，例如，在供体/受体卡宾的对映选择性转化中的用途。在某些实施例中，二铑催化剂包括一个环丙基环上取代有一个羧酸配体。在某些实施例中，该披露涉及包含以下式的化合物或其盐的组合物，其中R1、R2和R3在此处定义。
• US8975428B2
  申请人：——

  公开号：US8975428B2

  公开（公告）日：2015-03-10
• [EN] DIRHODIUM CATALYST COMPOSITIONS AND SYNTHETIC PROCESSES RELATED THERETO<br/>[FR] COMPOSITIONS DE CATALYSEUR DIRHODIUM ET PROCÉDÉS DE SYNTHÈSE S'Y RAPPORTANT
  申请人：UNIV EMORY

  公开号：WO2012167198A2

  公开（公告）日：2012-12-06

  This disclosure relates to compositions comprising dirhodium catalysts and uses related thereto, e.g., in enantioselective transformations of donor/acceptor carbenoids. In certain embodiments, the dirhodium catalyst comprises a cyclopropyl ring substituted with a carboxylic acid ligand. In certain embodiments, the disclosure relates to compositions comprising a compound of the following formula, or salts thereof wherein, R1, R2, and R3 are defined herein.
• [EN] AMINOOXAZOLE INHIBITORS OF CYCLIN DEPENDENT KINASES<br/>[FR] INHIBITEURS D'AMINOOXAZOLE DE KINASES DÉPENDANTES D'UNE CYCLINE
  申请人：NEOSOME LIFE SCIENCES LLC

  公开号：WO2012166463A2

  公开（公告）日：2012-12-06

  Oxazoie derivatives are described. The inventive compounds are useful as kinase inhibitors, and may be used in the treatment of cancer, such as prostate cancer, lung cancer, breast cancer, colon cancer, leukemia, CNS cancer, melanoma, ovarian cancer, and renal cancer.
• <i>D</i>₂-Symmetric Dirhodium Catalyst Derived from a 1,2,2-Triarylcyclopropanecarboxylate Ligand: Design, Synthesis and Application
  作者：Changming Qin、Vyacheslav Boyarskikh、Jørn H. Hansen、Kenneth I. Hardcastle、Djamaladdin G. Musaev、Huw M. L. Davies

  DOI：10.1021/ja2074104

  日期：2011.11.30

  Dirhodium tetrakis-(R)-(1-(4-bromophenyl)-2,2-diphenylcyclopropanecarboxylate) (Rh-2(R-BTPCP)(4)) was found to be an effective chiral catalyst for enantioselective reactions of aryl- and styryldiazoacetates. Highly enantioselective cyclopropanations, tandem cyclopropanation/Cope rearrangements and a combined C- functionalization/Cope rearrangement were achieved using Rh-2(R-BTPCP)(4) as catalyst. The advantages of Rh-2(R-BTPCP)(4) include its ease of synthesis, its tolerance to the size of the ester group in the styryldiazoacetates, and its compatibility with clichloromethane as solvent. Computational studies suggest that the catalyst adopts a D-2-symmetric arrangement, but when the carbenoid binds to the catalyst, two of the p-bromophenyl groups on the ligands rotate outward to make room for the carbenoid and the approach of the substrate to the carbenoid.