methyl (R,E)-2-((S)-4-methyl-1,2-dihydronaphthalen-2-yl)-4-phenylbut-3-enoate | 1345876-83-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl (R,E)-2-((S)-4-methyl-1,2-dihydronaphthalen-2-yl)-4-phenylbut-3-enoate
• 英文别名: (R,E)-methyl 2-((S)-4-methyl-1,2-dihydronaphthalen-2-yl)-4-phenylbut-3-enoate；methyl (E,2R)-2-[(2S)-4-methyl-1,2-dihydronaphthalen-2-yl]-4-phenylbut-3-enoate
• CAS: 1345876-83-6
• 化学式: C₂₂H₂₂O₂
• 分子量: 318.415
• InChiKey: WZDIENYTLRHYMF-BMPCTQGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  5
• 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：
  2

反应信息

• 作为产物：
  描述：

  4-甲基-1,2-二氢萘 、 (E)-methyl 2-diazo-4-phenylbut-3-enoate 在 dirhodium tetrakis((R)-1-(4-bromophenyl)-2,2-diphenylcyclopropanecarboxylate) 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到methyl (R,E)-2-((S)-4-methyl-1,2-dihydronaphthalen-2-yl)-4-phenylbut-3-enoate
  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。
• Composite Polymer/Oxide Hollow Fiber Contactors: Versatile and Scalable Flow Reactors for Heterogeneous Catalytic Reactions in Organic Synthesis
  作者：Eric G. Moschetta、Solymar Negretti、Kathryn M. Chepiga、Nicholas A. Brunelli、Ying Labreche、Yan Feng、Fateme Rezaei、Ryan P. Lively、William J. Koros、Huw M. L. Davies、Christopher W. Jones

  DOI：10.1002/anie.201500841

  日期：2015.5.26

  Flexible composite polymer/oxide hollow fibers are used as flow reactors for heterogeneously catalyzed reactions in organic synthesis. The fiber synthesis allows for a variety of supported catalysts to be embedded in the walls of the fibers, thus leading to a diverse set of reactions that can be catalyzed in flow. Additionally, the fiber synthesis is scalable (e.g. several reactor beds containing many

  柔性复合聚合物/氧化物中空纤维用作有机合成中非均相催化反应的流动反应器。纤维合成允许将多种负载型催化剂嵌入纤维壁中，从而导致可以在流动中催化的多种反应。另外，纤维的合成是可扩展的（例如，可以使用在模块中包含多个纤维的几个反应器床），因此它们有可能被用于大规模生产有机化合物。在纤维壁中掺入非均相催化剂是传统填充床反应器的一种替代选择，可避免大的压降，这在使用微反应器时是一个关键的挑战。
• 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.
• <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.