methyl 1,2-diphenylcyclopropane-1-carboxylate

• 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: methyl 1,2-diphenylcyclopropane-1-carboxylate
• 英文别名: methyl 1,2-diphenylcyclopropanecarboxylate
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: YAOZVDIKXMRFBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 1,2-diphenylcyclopropane-1-carboxylate 在 甲醇 、 1-氯-N,N,2-三甲基丙烯胺 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 (1,2-Diphenylcyclopropyl)-(4-methylpiperazin-1-yl)methanone
  参考文献：
  名称：

  Synthesis and biological characterization of a series of novel diaryl amide M1 antagonists

  摘要：

  Utilizing a combination of high-throughput and multi-step synthesis, SAR in a novel series of M-1 acetylcholine receptor antagonists was rapidly established. The efforts led to the discovery the highly potent M-1 antagonists 6 (VU0431263), and 8f (VU0433670). Functional Schild analysis and radioligand displacement experiments demonstrated the competitive, orthosteric binding of these compounds; human selectivity data are presented. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.011
• 作为产物：
  描述：

  Alpha-苯基-顺-肉桂酸 在 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 10.0h， 生成 methyl 1,2-diphenylcyclopropane-1-carboxylate
  参考文献：
  名称：

  Synthesis and biological characterization of a series of novel diaryl amide M1 antagonists

  摘要：

  Utilizing a combination of high-throughput and multi-step synthesis, SAR in a novel series of M-1 acetylcholine receptor antagonists was rapidly established. The efforts led to the discovery the highly potent M-1 antagonists 6 (VU0431263), and 8f (VU0433670). Functional Schild analysis and radioligand displacement experiments demonstrated the competitive, orthosteric binding of these compounds; human selectivity data are presented. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.011

文献信息

• Blue light-promoted cyclopropenizations of N-tosylhydrazones in water
  作者：Kaichuan Yan、Hua He、Jianglian Li、Yi Luo、Ruizhi Lai、Li Guo、Yong Wu

  DOI：10.1016/j.cclet.2021.05.031

  日期：2021.12

  Carbene transfer reactions play an important role in the field of organic synthesis because of their ability to construct a variety of molecules. Herein, we reported on blue light-induced cyclopropenizations of N-tosylhydrazones in water, which avoids the use of expensive metal-based catalysts and toxic organic solvents. This metal-free and operationally simple methodology enable highly efficient cyclopropenizations

  碳转移反应由于其能够构建多种分子的能力而在有机合成领域中起着重要作用。在本文中，我们报道了N-甲苯磺酰blue在水中的蓝光诱导环丙烷化反应，从而避免了使用昂贵的金属基催化剂和有毒有机溶剂。这种无金属且操作简单的方法可在温和的反应条件下实现高效的环丙烷化，XH插入反应和环丙烷化。
• Blue Light‐promoted Carbene Transfer Reactions of Tosylhydrazones
  作者：Yingying Xu、Guanghui Lv、Kaichuan Yan、Hua He、Jianglian Li、Yi Luo、Ruizhi Lai、Li Hai、Yong Wu

  DOI：10.1002/asia.202000378

  日期：2020.7

  Metal‐free photochemical carbene‐transfer reactions of tosylhydrazones were developed under blue light irradiation at room temperature. This reaction constructs C−X (X=C, N, O, S) bonds and cyclopropanes from readily available and stable starting materials.

  室温下在蓝光下进行了甲苯磺酰hydr的无金属光化学卡宾转移反应。该反应从容易获得且稳定的起始原料中构建CX（X = C，N，O，S）键和环丙烷。
• Highly Regio- and Enantioselective Formal [3 + 2]-Annulation of Indoles with Electrophilic Enol Carbene Intermediates
  作者：Changcheng Jing、Qing-Qing Cheng、Yongming Deng、Hadi Arman、Michael P. Doyle

  DOI：10.1021/acs.orglett.6b02192

  日期：2016.9.16

  formal [3 + 2]-annulation reactions of indoles and electrophilic enol carbenes. High enantioselectivity and exclusive regiocontrol occurred with enoldiazoacetamides using a less sterically encumbered prolinate-ligated dirhodium(II) catalyst in reactions with N-substituted indoles without substituents at the 2- or 3-positions via a selective vinylogous addition process. In this transformation, donor–acceptor

  手性环戊烷稠合的二氢吲哚通过吲哚和亲电子烯醇卡宾的正式[3 + 2]环化反应合成，具有高度的区域控制和对映控制。使用较少空间阻碍的脯氨酸盐连接的二碘（II）催化剂，通过选择性乙烯基醇加成反应，与2-或3-位无取代基的N-取代的吲哚反应，烯醇二乙酰胺发生了高对映选择性和排他性区域控制。在这种转化过程中，由烯丙基重氮乙酰胺生成的供体-受体环丙烯用作卡宾前体，形成金属卡宾中间体。
• Polynuclear Copper(I) Complexes with Chelating Bis- and Tris-N-Heterocyclic Carbene Ligands: Catalytic Activity in Nitrene and Carbene Transfer Reactions
  作者：Cristina Tubaro、Andrea Biffis、Riccardo Gava、Elena Scattolin、Andrea Volpe、Marino Basato、M. Mar Díaz-Requejo、Pedro J. Perez

  DOI：10.1002/ejoc.201101480

  日期：2012.3

  Di- and trinuclear complexes of copper(I) bearing bis- or tris-N-heterocyclic carbene ligands have been prepared and evaluated as catalysts in nitrene transfer reactions from PhI=NTs to unsaturated and saturated substrates (olefin aziridination and C–H bond amidation) and carbene transfer reactions from diazo compounds to olefins. The complexes exhibited moderate-to-high catalytic activity in both

  含双或三-N-杂环卡宾配体的铜（I）的双核和三核配合物已被制备并评估作为从PhI = NTs到不饱和和饱和底物（烯烃氮丙啶化和C-H键酰胺化）的氮烯转移反应的催化剂) 和卡宾从重氮化合物到烯烃的转移反应。复合物在这两个过程中都表现出中到高的催化活性。双核配合物促进了 C-H 键的甲苯磺酰胺化，以前没有报道过使用含 NHC 的铜催化剂。
• Determination of orientational isomerism in rhodium(ii) metallopeptides by pyrene fluorescence
  作者：Ramya Sambasivan、Zachary T. Ball

  DOI：10.1039/c2ob26667a

  日期：——

  Rhodium(II) metallopeptides display useful secondary structure, self-assembly, and catalytic activity. The bis-peptide complexes exhibit subtle orientational isomerism that affects function, but is challenging to characterize. We report that pyrene excimer fluorescence measurements provide a conclusive proof of isomeric structure.

  铑（II）金属肽显示出有用的二级结构、自组装和催化活性。双肽复合物表现出微妙的取向异构性，会影响其功能，但对其进行表征具有挑战性。我们报告说，芘准分子荧光测量为异构结构提供了确凿的证据。