1-cyclopropyl-3,3-dimethyl-1-(pent-3-yn-1-yl)urea | 1428156-81-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: 1-cyclopropyl-3,3-dimethyl-1-(pent-3-yn-1-yl)urea
• 英文别名: 1-Cyclopropyl-3,3-dimethyl-1-pent-3-ynylurea
• CAS: 1428156-81-3
• 化学式: C₁₁H₁₈N₂O
• 分子量: 194.277
• InChiKey: JGCSBKCDVCOION-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-cyclopropyl-3,3-dimethyl-1-(pent-3-yn-1-yl)urea 在 bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate 、 copper(l) iodide 、 三[3,4-双(三氟甲基)苯基]膦 作用下， 以 四氢呋喃 、 正己烷 、 苯甲腈 为溶剂， -78.0~130.0 ℃ 、101.33 kPa 条件下， 反应 29.17h， 生成 3a-butyl-N,N,4-trimethyl-5-oxooctahydro-1H-indole-1-carboxamide 、 3a-butyl-N,N,4-trimethyl-5-oxooctahydro-1H-indole-1-carboxamide
  参考文献：
  名称：

  Directed carbonylative (3+1+2) cycloadditions of amino-substituted cyclopropanes and alkynes: reaction development and increased efficiencies using a cationic rhodium system

  摘要：

  Urea-directed carbonylative insertion of Rh(I)-catalysts into one of the two proximal C-C bonds of aminocyclopropanes generates rhodacyclopentanone intermediates. These are trapped by N-tethered alkynes to provide a (3+1+2) cycloaddition protocol that accesses N-heterobicyclic enones. Stoichiometric studies on a series of model rhodacyclopentanone complexes outline key structural features and provide a rationale for the efficacy of urea directing groups. A comprehensive evaluation of cycloaddition scope and a 'second generation' cationic Rh(I)-system, which provides enhanced yields and reaction rates for challenging substrates, are presented. (C) 2015 The Authors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2015.08.052
• 作为产物：
  描述：

  3-戊炔-1-醇 在 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 50.0h， 生成 1-cyclopropyl-3,3-dimethyl-1-(pent-3-yn-1-yl)urea
  参考文献：
  名称：

  Directing Group Enhanced Carbonylative Ring Expansions of Amino-Substituted Cyclopropanes: Rhodium-Catalyzed Multicomponent Synthesis of N-Heterobicyclic Enones

  摘要：

  Aminocyclopropanes equipped with suitable N-directing groups undergo efficient and regioselective Rh-catalyzed carbonylative C-C bond activation. Trapping of the resultant metallacycles with tethered alkynes provides an atom-economic entry to diverse N-heterobicyclic enones. These studies provide a blueprint for myriad N-heterocyclic methodologies.

  DOI：

  10.1021/ja401936c