(1R,2S,3R)-2-benzoyl-3-propylcyclopropane-1-carbaldehyde | 849582-79-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,3R)-2-benzoyl-3-propylcyclopropane-1-carbaldehyde
• 英文别名: (1R,2S,3R)-2-benzoyl-3-propyl-cyclopropanecarbaldehyde；(1R,2S,3R)-2-benzoyl-3-propylcyclopropanecarbaldehyde
• CAS: 849582-79-2
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: OOPDJZVELSRONO-UPJWGTAASA-N

物化性质

• 沸点：
  331.2±35.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  (1R,2S,3R)-2-benzoyl-3-propylcyclopropane-1-carbaldehyde 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 4.0h， 以63%的产率得到6-phenyl-4-propyl-3,4-dihydropyran-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：

  1-pentenol 、 (benzoylmethylene)dimethylsulfurane 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以47%的产率得到(1R,2S,3R)-2-benzoyl-3-propylcyclopropane-1-carbaldehyde
  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

文献信息

• 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。
• 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.
• Tetrazolic Acid Functionalized Dihydroindol:  Rational Design of a Highly Selective Cyclopropanation Organocatalyst
  作者：Antti Hartikka、Per I. Arvidsson

  DOI：10.1021/jo070519e

  日期：2007.7.1

  Herein we wish to report our development of an improved catalyst (S)-(-)-indoline-2-yl-1H-tetrazole (1) for the enantioselective organocatalyzed cyclopropanation of alpha,beta-unsaturated aldehydes with sulfur ylides. The new organocatalyst readily facilitates the enantioselective organocatalytic cyclopropanation, providing cyclized product in excellent diastereoselectivities ranging from 96% to 98% along with enantioselectivities exceeding 99% enantiomeric excess for all reacted alpha,beta-unsaturated aldehydes. The new catalyst provides the best results so far reported for intermolecular enantioselective organocatalyzed cyclopropanation.
• N-Heterocyclic Carbene Catalyzed CC Bond Cleavage in Redox Esterifications of Chiral Formylcyclopropanes
  作者：Stephanie S. Sohn、Jeffrey W. Bode

  DOI：10.1002/anie.200601919

  日期：2006.9.11
• Organocatalytic asymmetric cyclopropanation of α,β-unsaturated aldehydes with arsonium ylides
  作者：Yun-Hui Zhao、Gang Zhao、Wei-Guo Cao

  DOI：10.1016/j.tetasy.2007.10.007

  日期：2007.10

  A novel organocatalytic asymmetric cyclopropanation of alpha,beta-unsaturated aldehydes with arsonium ylides using diphenylprolinol silylether as a catalyst is described. A variety of chiral cyclopropyl aldehydes are obtained in moderate to good yields with up to 99:1 dr (diastereomeric ratio) and 99% ee under simple and mild reaction conditions. (c) 2007 Elsevier Ltd. All rights reserved.