tert-butyl N-[(2S)-1-chloro-3-methylbutan-2-yl]carbamate | 183990-23-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: tert-butyl N-[(2S)-1-chloro-3-methylbutan-2-yl]carbamate
• CAS: 183990-23-0
• 化学式: C₁₀H₂₀ClNO₂
• 分子量: 221.727
• InChiKey: WLSDBQWBTPQYBV-MRVPVSSYSA-N

物化性质

• 沸点：
  288.0±23.0 °C(Predicted)
• 密度：
  1.016±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二氧化碳 、 tert-butyl N-[(2S)-1-chloro-3-methylbutan-2-yl]carbamate 在 正丁基锂 、 LiC₁₀H₇ 作用下， 生成 叔丁氧羰基-β-亮氨酸
  参考文献：
  名称：

  EPC-Synthesis of functionalised amides via chiral β-nitrogenated organolithium compounds

  摘要：

  The deprotonation of chiral chloroamides or carbamates 1, 4, 7, 10, 13 and 16 with n-butyllithium followed by in situ lithiation with lithium naphthalenide, both at -78 degrees C in THF, leads to the formation of the corresponding chiral dianionic intermediates, which by reaction with different electrophiles [H2O, D2O, Me(2)S(2), (CH2)(5)CO, Bu(t)CHO, PhCHO, CO2, CO(OEt)(2), BrCH(2)CO(2)Et and DCC] at -78 to 20 degrees C affords, after hydrolysis with water, the expected enantiopure compounds. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00382-5
• 作为产物：
  描述：

  L-缬氨醇 在 氯化亚砜 、 sodium carbonate 、 三乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 5.0h， 生成 tert-butyl N-[(2S)-1-chloro-3-methylbutan-2-yl]carbamate
  参考文献：
  名称：

  EPC-Synthesis of functionalised amides via chiral β-nitrogenated organolithium compounds

  摘要：

  The deprotonation of chiral chloroamides or carbamates 1, 4, 7, 10, 13 and 16 with n-butyllithium followed by in situ lithiation with lithium naphthalenide, both at -78 degrees C in THF, leads to the formation of the corresponding chiral dianionic intermediates, which by reaction with different electrophiles [H2O, D2O, Me(2)S(2), (CH2)(5)CO, Bu(t)CHO, PhCHO, CO2, CO(OEt)(2), BrCH(2)CO(2)Et and DCC] at -78 to 20 degrees C affords, after hydrolysis with water, the expected enantiopure compounds. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00382-5

文献信息

• EPC-Synthesis of functionalised amides via chiral β-nitrogenated organolithium compounds
  作者：Francisco Foubelo、Miguel Yus

  DOI：10.1016/0957-4166(96)00382-5

  日期：1996.10

  The deprotonation of chiral chloroamides or carbamates 1, 4, 7, 10, 13 and 16 with n-butyllithium followed by in situ lithiation with lithium naphthalenide, both at -78 degrees C in THF, leads to the formation of the corresponding chiral dianionic intermediates, which by reaction with different electrophiles [H2O, D2O, Me(2)S(2), (CH2)(5)CO, Bu(t)CHO, PhCHO, CO2, CO(OEt)(2), BrCH(2)CO(2)Et and DCC] at -78 to 20 degrees C affords, after hydrolysis with water, the expected enantiopure compounds. Copyright (C) 1996 Elsevier Science Ltd