(E)-methyl 4-(2-cyclopropylvinyl)benzoate | 1190899-28-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-methyl 4-(2-cyclopropylvinyl)benzoate
• 英文别名: methyl 4-[(E)-2-cyclopropylethenyl]benzoate
• CAS: 1190899-28-5
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: LEJWXPLJNMGYDR-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  (E)-methyl 4-(2-cyclopropylvinyl)benzoate 在 bis(1,5-cyclooctadiene)nickel (0) 、 二茂铁 、 1,3-双(2,6-二异丙基苯基)咪唑-2-烯 作用下， 以 氘代苯 为溶剂， 生成 methyl 4-(cyclopent-2-enyl)benzoate
  参考文献：
  名称：

  Mechanism of the Ni(0)-Catalyzed Vinylcyclopropane−Cyclopentene Rearrangement

  摘要：

  A combination of physical organic experiments and quantum chemical calculations were used to construct a detailed mechanistic model for the Ni(0)-N-heterocyclic carbene-catalyzed vinylcyclo-propane-cyclopentene rearrangement that involves a mutistep oxidative addition/haptotropic shift/reductive elimination pathway. No evidence for the intermediacy of radicals or zwitterions was found. The roles of substituents on the vinylcyclopropane substrate and variations in the ligands on Ni were evaluated. It is postulated that bulky carbene ligands facilitate formation of the active catalyst species.

  DOI：

  10.1021/jo901525u
• 作为产物：
  描述：

  (4-甲氧羰基苄基)三苯基溴化膦 、 环丙甲醛 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 生成 (Z)-methyl 4-(2-cyclopropylvinyl)benzoate 、 (E)-methyl 4-(2-cyclopropylvinyl)benzoate
  参考文献：
  名称：

  Mechanism of the Ni(0)-Catalyzed Vinylcyclopropane−Cyclopentene Rearrangement

  摘要：

  A combination of physical organic experiments and quantum chemical calculations were used to construct a detailed mechanistic model for the Ni(0)-N-heterocyclic carbene-catalyzed vinylcyclo-propane-cyclopentene rearrangement that involves a mutistep oxidative addition/haptotropic shift/reductive elimination pathway. No evidence for the intermediacy of radicals or zwitterions was found. The roles of substituents on the vinylcyclopropane substrate and variations in the ligands on Ni were evaluated. It is postulated that bulky carbene ligands facilitate formation of the active catalyst species.

  DOI：

  10.1021/jo901525u

文献信息

• ANTIBACTERIAL AGENTS
  申请人：Moser Heinz E.

  公开号：US20100190766A1

  公开（公告）日：2010-07-29

  Antibacterial compounds of formula (I) are provided: as well as stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of such compounds.

  提供化学式(I)的抗菌化合物：以及其立体异构体，药学上可接受的盐，酯和前药；包含这些化合物的制药组合物；通过给予这些化合物的途径治疗细菌感染的方法；以及制备这些化合物的过程。
• [EN] ANTIBACTERIAL AGENTS<br/>[FR] AGENTS ANTIBACTÉRIENS
  申请人：ACHAOGEN INC

  公开号：WO2008154642A2

  公开（公告）日：2008-12-18

  [EN] Antibacterial compounds of formula (I) are provided, as well as stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of such compounds.
  [FR] L'invention propose des composés antibactériens de formule (I), ainsi que des stéréoisomères, des sels pharmaceutiques acceptables, des esters et des promédicaments de ceux-ci ; des compositions pharmaceutiques comportant de tels composés ; des procédés de traitement d'infections bactériennes par l'administration de tels composés ; et des procédés pour la préparation de tels composés.
• Mechanism of the Ni(0)-Catalyzed Vinylcyclopropane−Cyclopentene Rearrangement
  作者：Selina C. Wang、Dawn M. Troast、Martin Conda-Sheridan、Gang Zuo、Donna LaGarde、Janis Louie、Dean J. Tantillo

  DOI：10.1021/jo901525u

  日期：2009.10.16

  A combination of physical organic experiments and quantum chemical calculations were used to construct a detailed mechanistic model for the Ni(0)-N-heterocyclic carbene-catalyzed vinylcyclo-propane-cyclopentene rearrangement that involves a mutistep oxidative addition/haptotropic shift/reductive elimination pathway. No evidence for the intermediacy of radicals or zwitterions was found. The roles of substituents on the vinylcyclopropane substrate and variations in the ligands on Ni were evaluated. It is postulated that bulky carbene ligands facilitate formation of the active catalyst species.