tert-butyl N-(2-oxoethyl)-N-(3-phenylprop-2-ynyl)carbamate | 927383-88-8

• 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: tert-butyl N-(2-oxoethyl)-N-(3-phenylprop-2-ynyl)carbamate
• CAS: 927383-88-8
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: DAYQRNWADIKXEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-(2-oxoethyl)-N-(3-phenylprop-2-ynyl)carbamate 、 alkaline earth salt of/the/ methylsulfuric acid 以 四氢呋喃 为溶剂， 反应 0.25h， 以70%的产率得到N-tert-butoxycarbonyl-3-phenyl-2,4,6,6a-tetrahydrofuro[2,3-c]pyrrol-2-one
  参考文献：
  名称：

  Butenolide Synthesis by Molybdenum-Mediated Hetero-Pauson−Khand Reaction of Alkynyl Aldehydes

  摘要：

  The highly reactive complex Mo(CO)(3)(DMF)(3) promotes the CO gas-free cyclocarbonylation of 1,5- and 1,6-alkynyl aldehydes under very mild reaction conditions to provide fused butenolides in good yields. This novel Mo-mediated hetero-Pauson-Khand reaction is very general with regard to the substitution at the alkyne terminus and tether (18 tested cases). Using readily available chiral alkynyl aldehydes, this procedure has been applied to the enantio- and stereoselective synthesis of highly substituted bicyclic butenolides, including an intermediate in natural product synthesis.

  DOI：

  10.1021/ja0684186
• 作为产物：
  描述：

  tert-butyl (2-hydroxyethyl)(prop-2-yn-1-yl)carbamate 在 palladium diacetate copper(l) iodide 、 戴斯-马丁氧化剂 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 13.0h， 生成 tert-butyl N-(2-oxoethyl)-N-(3-phenylprop-2-ynyl)carbamate
  参考文献：
  名称：

  Butenolide Synthesis by Molybdenum-Mediated Hetero-Pauson−Khand Reaction of Alkynyl Aldehydes

  摘要：

  The highly reactive complex Mo(CO)(3)(DMF)(3) promotes the CO gas-free cyclocarbonylation of 1,5- and 1,6-alkynyl aldehydes under very mild reaction conditions to provide fused butenolides in good yields. This novel Mo-mediated hetero-Pauson-Khand reaction is very general with regard to the substitution at the alkyne terminus and tether (18 tested cases). Using readily available chiral alkynyl aldehydes, this procedure has been applied to the enantio- and stereoselective synthesis of highly substituted bicyclic butenolides, including an intermediate in natural product synthesis.

  DOI：

  10.1021/ja0684186

文献信息

• Butenolide Synthesis by Molybdenum-Mediated Hetero-Pauson−Khand Reaction of Alkynyl Aldehydes
  作者：Javier Adrio、Juan C. Carretero

  DOI：10.1021/ja0684186

  日期：2007.1.1

  The highly reactive complex Mo(CO)(3)(DMF)(3) promotes the CO gas-free cyclocarbonylation of 1,5- and 1,6-alkynyl aldehydes under very mild reaction conditions to provide fused butenolides in good yields. This novel Mo-mediated hetero-Pauson-Khand reaction is very general with regard to the substitution at the alkyne terminus and tether (18 tested cases). Using readily available chiral alkynyl aldehydes, this procedure has been applied to the enantio- and stereoselective synthesis of highly substituted bicyclic butenolides, including an intermediate in natural product synthesis.