isopropenyl chloroformate | 1026672-53-6

• 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: isopropenyl chloroformate
• 英文别名: 3-Methylbut-3-enyl carbonochloridate
• CAS: 1026672-53-6
• 化学式: C₆H₉ClO₂
• 分子量: 148.589
• InChiKey: ISCVEKSMPLIGHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  158.1±19.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  isopropenyl chloroformate 在 吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 0.5h， 生成 Alpha,Alpha-二甲基-γ-丁内酯
  参考文献：
  名称：

  Bachi, Mario D.; Bosch, Eric, Heterocycles, 1989, vol. 28, # 2, p. 579 - 582

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲基-3-丁烯-1-醇 、 光气 以 苯 为溶剂， 生成 isopropenyl chloroformate
  参考文献：
  名称：

  Synthesis of .gamma.- and .delta.-lactones by free-radical annelation of Se-phenyl selenocarbonates

  摘要：

  A general method for the synthesis of gamma- and delta-lactones through the intramolecular addition of alkoxycarbonyl radicals, formed by reaction of Se-phenylselenocarbonates with n-Bu3SnH, onto carbon-carbon multiple bonds is described. This free-radical cyclization is characterized by high regioselectivity favoring exo addition and by a high ratio of cyclization to reduction. Monocyclic, fused bicyclic, and spirocyclic lactones are formed in good to excellent yield. Use of allyltri-n-butyltin as a chain-transfer agent in the place of n-Bu3SnH affords the corresponding 3-butenyl lactones.

  DOI：

  10.1021/jo00043a030
• 作为试剂：
  描述：

  N-苄氧羰基-缬氨酰-苯基丙氨酸甲酯 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 isopropenyl chloroformate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 benzyl N-[(2S)-1-[(2S,3S)-2-benzyl-3-hydroxy-5-oxopyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate
  参考文献：
  名称：

  Hydroxyoxazolidines as α-aminoacetaldehyde equivalents: Novel inhibitors of calpain

  摘要：

  The synthesis of [1-[(5-hydroxy-4-(phenylmethyl)-3-oxazolidinyl)carbonyl]-2-ethylpropyl] carbamic acid phenylmethyl ester (2; MDL 104,903), a potent inhibitor of calpain, is described. Synthesis of related compounds, which offer insights into the mechanism of action for 2, are also described, as is an O-acetyl prodrug derivative of 2. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00391-1

文献信息

• Bachi, Mario D.; Bosch, Eric, Heterocycles, 1989, vol. 28, # 2, p. 579 - 582
  作者：Bachi, Mario D.、Bosch, Eric

  DOI：——

  日期：——
• Synthesis of .gamma.- and .delta.-lactones by free-radical annelation of Se-phenyl selenocarbonates
  作者：Mario D. Bachi、Eric Bosch

  DOI：10.1021/jo00043a030

  日期：1992.8

  A general method for the synthesis of gamma- and delta-lactones through the intramolecular addition of alkoxycarbonyl radicals, formed by reaction of Se-phenylselenocarbonates with n-Bu3SnH, onto carbon-carbon multiple bonds is described. This free-radical cyclization is characterized by high regioselectivity favoring exo addition and by a high ratio of cyclization to reduction. Monocyclic, fused bicyclic, and spirocyclic lactones are formed in good to excellent yield. Use of allyltri-n-butyltin as a chain-transfer agent in the place of n-Bu3SnH affords the corresponding 3-butenyl lactones.