trans-1,2-diphenyl-1-cyclopropanecarboxylic acid | 42333-02-8

• 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: trans-1,2-diphenyl-1-cyclopropanecarboxylic acid
• 英文别名: (Z)-1,2-diphenylcyclopropanecarboxylic acid；cis-1,2-diphenylcyclopropane-1-carboxylic acid；(Z)-1,2-Diphenylcyclopropancarbonsaeure；(1S,2R)-1,2-diphenylcyclopropanecarboxylic acid；(1S,2R)-1,2-diphenylcyclopropane-1-carboxylic acid
• CAS: 42333-02-8
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: FRACCHQHBCIENL-GDBMZVCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-1,2-diphenyl-1-cyclopropanecarboxylic acid 在 硫酸 作用下， 以67%的产率得到2,4-diphenyl-γ-butyrolactone
  参考文献：
  名称：

  Sychkova, L. D.; Kharitonova, O. V.; Shabarov, Yu. S., Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 1298 - 1301

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 2-diethoxyphosphoryl-2-phenylacetate 在 正丁基锂 、 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 为溶剂， 反应 2.91h， 生成 trans-1,2-diphenyl-1-cyclopropanecarboxylic acid
  参考文献：
  名称：

  Synthesis, biological activity and mechanistic insights of 1-substituted cyclopropylamine derivatives: A novel class of irreversible inhibitors of histone demethylase KDM1A

  摘要：

  Histone demethylase KDM1A (also known as LSD1) has become an attractive therapeutic target for the treatment of cancer as well as other disorders such as viral infections. We report on the synthesis of compounds derived from the expansion of tranylcypromine as a chemical scaffold for the design of novel demethylase inhibitors. These compounds, which are substituted on the cyclopropyl core moiety, were evaluated for their ability to inhibit KDM1A in vitro as well as to function in cells by modulating the expression of Gfi-1b, a well recognized KDM1A target gene. The molecules were all found to covalently inhibit KDM1A and to become increasingly selective against human monoamine oxidases MAO A and MAO B through the introduction of bulkier substituents on the cyclopropylamine ring. Structural and biochemical analysis of selected trans isomers showed that the two stereoisomers are endowed with similar inhibitory activities against KDM1A, but form different covalent adducts with the FAD co-enzyme. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.068

文献信息

• Enantioselective dirhodium(II)-catalyzed cyclopropanations with trimethylsilylethyl and trichloroethyl aryldiazoacetates
  作者：Solymar Negretti、Carolyn M. Cohen、Jane J. Chang、David M. Guptill、Huw M.L. Davies

  DOI：10.1016/j.tet.2015.05.045

  日期：2015.9

  readily prepared by rhodium-catalyzed cyclopropanation of alkenes with aryldiazoacetates and styryldiazoaceates, in which the ester functionality is either trimethylsilylethyl (TMSE) or trichloroethyl (TCE). By having labile protecting groups on the ester, chiral triarylcyclopropane carboxylate ligands were conveniently prepared. The asymmetric induction during cyclopropanation is dependent on the

  通过用芳基重氮乙酸酯和苯乙烯基二重氮酸酯对烯烃进行铑催化的环丙烷化，可以轻松制备高度官能化的环丙烷羧酸酯，其中酯官能度为三甲基甲硅烷基乙基（TMSE）或三氯乙基（TCE）。通过在酯上具有不稳定的保护基，可以方便地制备手性三芳基环丙烷羧酸酯配体。环丙烷化过程中的不对称诱导取决于酯基和手性四羧酸四氢吡啶鎓催化剂的性质。脯氨酸盐催化剂Rh 2（S -DOSP）4是TMSE重氮酯与苯乙烯不对称分子间环丙烷化的最佳催化剂，而Rh 2（R -BPCP）4 是TCE重氮酯的最佳催化剂。
• Tertiary cyclopropyl carbagermatranes: synthesis and cross-coupling
  作者：Shuo Yang、Wei-Tao Jiang、Bin Xiao

  DOI：10.1039/d1cc02930d

  日期：——

  The construction of the cyclopropyl quaternary carbon center can afford a series of 1,1-olefin bioisosteres. Here, we report tertiary cyclopropyl carbagermatranes, which can be easily obtained by the zinc-mediated decarboxylation of NHP esters. In addition, they exhibit efficient reactivity in the palladium-catalyzed cross-coupling reaction and orthogonal reactivity with boron reagents, therefore acting

  环丙基季碳中心的构建可以提供一系列1,1-烯烃生物等排体。在这里，我们报告了叔环丙基卡巴格马酯，它可以通过锌介导的 NHP 酯的脱羧轻松获得。此外，它们在钯催化的交叉偶联反应中表现出有效的反应性以及与硼试剂的正交反应性，因此可用作合成叔环丙烷的强亲核试剂和形成季中心的有效中间体。
• 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。
• Dirhodium catalyst compositions and synthetic processes related thereto
  申请人：Davies Huw M. L.

  公开号：US08975428B2

  公开（公告）日：2015-03-10

  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.

  本公开涉及包含双铑催化剂的组合物及其相关用途，例如，在供体/受体卡宾化合物的对映选择性转化中的应用。在某些实施例中，双铑催化剂包括一个被羧酸配体取代的环丙基环。在某些实施例中，本公开涉及包含以下化合物或其盐的组合物，其中，R1、R2和R3如本文所定义。
• <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.