2,2,2-trichloroethyl N,N-diisopropylcarbamate | 444673-08-9

• 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: 2,2,2-trichloroethyl N,N-diisopropylcarbamate
• CAS: 444673-08-9
• 化学式: C₉H₁₆Cl₃NO₂
• 分子量: 276.591
• InChiKey: PCESEPHSHVUXIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,2,2-trichloroethyl N,N-diisopropylcarbamate 在 lithium diisopropyl amide 、 甲醇 作用下， 以 乙醚 、 正己烷 为溶剂， 以90%的产率得到2,2-dichloroethenyl N,N-diisopropylcarbamate
  参考文献：
  名称：

  Synthesis of an Ethynyl Carbamate and Application for Enantioselective Cyclocarbolithiation

  摘要：

  [GRAPHICS]The intramolecular trans-cyclocarbolithiation of the alpha-lithiated 4-substituted 5-hexynyl carbamate (1S,4RS)-14 employing lithiodestannylation is presented. The 5-exo-dig cyclization products cis-/trans-16a were formed exclusively. The highly enantioenriched organotin precursor (S)-11 was synthesized via an asymmetric deprotonation of the corresponding alkyl carbarnate 10 by the chiral complex sec-butyllithium/(-)sparteine and subsequent substitution with tributyltin chloride.

  DOI：

  10.1021/ol0260674
• 作为产物：
  描述：

  2,2,2-三氯乙醇 、 二异丙基甲胺酰氯 以 吡啶 为溶剂， 反应 16.0h， 以81%的产率得到2,2,2-trichloroethyl N,N-diisopropylcarbamate
  参考文献：
  名称：

  Synthesis of an Ethynyl Carbamate and Application for Enantioselective Cyclocarbolithiation

  摘要：

  [GRAPHICS]The intramolecular trans-cyclocarbolithiation of the alpha-lithiated 4-substituted 5-hexynyl carbamate (1S,4RS)-14 employing lithiodestannylation is presented. The 5-exo-dig cyclization products cis-/trans-16a were formed exclusively. The highly enantioenriched organotin precursor (S)-11 was synthesized via an asymmetric deprotonation of the corresponding alkyl carbarnate 10 by the chiral complex sec-butyllithium/(-)sparteine and subsequent substitution with tributyltin chloride.

  DOI：

  10.1021/ol0260674