2-benzoyl-3-phenyl-cyclopropanecarbaldehyde

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-benzoyl-3-phenyl-cyclopropanecarbaldehyde
• 英文别名: (1R,2S,3R)-2-benzoyl-3-phenylcyclopropane-1-carbaldehyde
• 化学式: C₁₇H₁₄O₂
• 分子量: 250.297
• InChiKey: JAWHAAIAYFZUPR-BZUAXINKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-benzoyl-3-phenyl-cyclopropanecarbaldehyde 在 2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以92%的产率得到4,6-diphenyl-3,4-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  N-Heterocyclic Carbene Catalyzed Ring Expansion of Formylcyclopropanes: Synthesis of 3,4-Dihydro-α-pyrone Derivatives

  摘要：

  N-Heterocyclic carbene catalyzed ring expansion of readily accessible 2-acyl-l-formylcyclopropanes was developed. With 5 mol % of triazoliurn salt 5 and 30 mol % of DBU, ring expansion of various 2-acyl-l-formylcyclopropanes led to 3,4-dihydro-alpha-pyrones in good to excellent yields.

  DOI：

  10.1021/ol9002898
• 作为产物：
  描述：

  (R)-((1S,2R,3R)-2-(hydroxymethyl)-3-phenylcyclopropyl)(phenyl)methanol 在 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 生成 2-benzoyl-3-phenyl-cyclopropanecarbaldehyde
  参考文献：
  名称：

  通过氧化N杂环卡宾催化对映体对映体的对映选择性环丙烷化。

  摘要：

  碳催化的α，β-不饱和醛的氧化还原活化被用于产生α，β-不饱和酰基偶氮，其在与硫内酯和醇反应后进行环丙烷化，得到相应的环丙烷羧酸酯。使用手性碳烯，可以获得极佳的非对映异构性和对映选择性。

  DOI：

  10.1039/c2cc31501g

文献信息

• Arylation of Aldehydes To Directly Form Ketones via Tandem Nickel Catalysis
  作者：Chuanhu Lei、Daoyong Zhu、Vicente III Tiu Tangcueco、Jianrong Steve Zhou

  DOI：10.1021/acs.orglett.9b01782

  日期：2019.8.2

  both aliphatic and aromatic aldehydes proceeds with air-stable (hetero)arylboronic acids, with an exceptionally wide substrate scope. The neutral condition tolerates acidic hydrogen and sensitive polar groups and also preserves α-stereocenters of some chiral aldehydes. Interestingly, this nickel(0) catalysis does not follow common 1,2-insertion of arylmetal species to aldehydes and β-hydrogen elimination

  脂族和芳族醛的镍催化芳基化反应与空气稳定的（杂）芳基硼酸一起进行，底物范围特别宽。中性条件耐受酸性氢和敏感的极性基团，并且还保留了一些手性醛的α-立体中心。有趣的是，这种镍（0）催化反应并不遵循芳基金属物种对醛和β-氢消除的常见1,2-插入。
• Enantioselective Organocatalytic Cyclopropanations. The Identification of a New Class of Iminium Catalyst Based upon Directed Electrostatic Activation
  作者：Roxanne K. Kunz、David W. C. MacMillan

  DOI：10.1021/ja042774b

  日期：2005.3.1

  A new method for enantioselective organocatalytic cyclopropanation is described. This study outlines the identification of a new class of iminium catalyst based on the concept of directed electrostatic activation (DEA). This novel organocatalytic mechanism exploits dual activation of ylide and enal substrates through a proposed electrostatic activation and stereodirected protocol. Formation of trisubstituted

  描述了一种对映选择性有机催化环丙烷化的新方法。本研究概述了基于定向静电活化 (DEA) 概念的新型亚胺催化剂的鉴定。这种新颖的有机催化机制通过提出的静电激活和立体定向协议利用了叶立德和 enal 底物的双重激活。对多种α、β-不饱和醛和锍叶立德可形成具有高水平对映和非对映诱导的三取代环丙烷。此外，机理研究发现，该环丙烷化反应表现出与提议的 DEA 步骤一致的对映选择性和反应性特征。
• Peptide-Catalyzed Diastereo- and Enantioselective Cyclopropanation of Aromatic α,β-Unsaturated Aldehydes
  作者：Kengo Akagawa、Shota Takigawa、Iman Sho Nagamine、Ryota Umezawa、Kazuaki Kudo

  DOI：10.1021/ol402227y

  日期：2013.10.4

  Highly diastereo- and enantioselective cyclopropanation of aromatic α,β-unsaturated aldehydes was achieved using a resin-supported peptide catalyst under aqueous conditions. In the peptide sequence, the residue possessing an oxygen atom with the appropriate length of the side chain was essential for attaining good diastereoselectivity.

  使用树脂负载的肽催化剂在水性条件下，可以实现芳族α，β-不饱和醛的高度非对映和对映选择性环丙烷化。在肽序列中，具有氧原子且侧链长度合适的残基对于获得良好的非对映选择性至关重要。
• N-Heterocyclic Carbene-Catalyzed Redox Amidations of α-Functionalized Aldehydes with Amines
  作者：Jeffrey W. Bode、Stephanie S. Sohn

  DOI：10.1021/ja0768136

  日期：2007.11.1

  A catalytic method for the direct synthesis of carboxylic acid amides from amines and alpha-functionalized aldehydes is possible through the synergistic role of a N-heterocyclic carbene catalyst and imidazole, affording amides via activated carboxylates catalytically generated via an internal redox reaction of the aldehyde substrates. The use of imidazole or other N-heterocycles as an additive is essential to overcoming imine formation and serves as a uniquely reactive substrate for the generation of an acyl imidazolium intermediate that is converted to the final amide product.
• Application of novel sulfonamides in enantioselective organocatalyzed cyclopropanation
  作者：Antti Hartikka、Adam T. Ślósarczyk、Per I. Arvidsson

  DOI：10.1016/j.tetasy.2007.05.030

  日期：2007.7

  Three novel aryl sulfonamides derived from (2S)-indoline-2-carboxylic acid have been obtained and used as organocatalysts. The catalysts incorporate diverse functionality on the phenyl ring, enabling steric, and electronic fine tuning of the catalysts. The catalysts facilitate the reaction between a range of alpha, beta-unsaturated aldehydes and sulfur ylides, thus providing cyclopropane products in enantiomeric excesses of up to 99%. (c) 2007 Elsevier Ltd. All rights reserved.