(S)-3-methyl-2-(N-tert-butoxycarbonylprop-2-ynylamino)butanal | 927384-06-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-3-methyl-2-(N-tert-butoxycarbonylprop-2-ynylamino)butanal
• 英文别名: tert-butyl N-[(2S)-3-methyl-1-oxobutan-2-yl]-N-prop-2-ynylcarbamate
• CAS: 927384-06-3
• 化学式: C₁₃H₂₁NO₃
• 分子量: 239.315
• InChiKey: KPQZDMVTMMMXNK-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  (S)-3-methyl-2-(N-tert-butoxycarbonylprop-2-ynylamino)butanal 、 alkaline earth salt of/the/ methylsulfuric acid 在 三乙基硼 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 (6S,6aR)-N-tert-butoxycarbonyl-6,6a-dihydro-6-isopropyl-2-oxo-2H-furo[3,2-c]-5-pyrrole 、 (6S,6aS)-N-tert-butoxycarbonyl-6,6a-dihydro-6-isopropyl-2-oxo-2H-furo[3,2-c]-5-pyrrole
  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：

  methyl (S)-3-methyl-2-(2-propynylamino)butanoate 在 sodium hydroxide 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 (S)-3-methyl-2-(N-tert-butoxycarbonylprop-2-ynylamino)butanal
  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