(Z)-buta-1,3-dien-1-yl diisopropylcarbamate

• 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: (Z)-buta-1,3-dien-1-yl diisopropylcarbamate
• 英文别名: [(1Z)-buta-1,3-dienyl] N,N-di(propan-2-yl)carbamate
• 化学式: C₁₁H₁₉NO₂
• 分子量: 197.277
• InChiKey: YNTDLYYDJSCZLW-FPLPWBNLSA-N

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：
  0.55
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  a-叠氮基-苯乙酸甲酯 、 (Z)-buta-1,3-dien-1-yl diisopropylcarbamate 在 lithium aluminium tetrahydride 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.17h， 生成 2-(hydroxymethyl)-2-phenyl-3-vinylcyclopropyl diisopropylcarbamate
  参考文献：
  名称：

  Copper-Catalyzed Regiospecific and 1,2-Regioselective Cyclopropanation of (1Z)-1-Amino- and (1Z)-1-Oxy-1,3-butadienyl Derivatives

  摘要：

  The copper-catalyzed regiospecific and 1,2-regioselective cyclopropanation of (1Z)-1-amino- and (1Z)-1-oxy-1,3-butadienyl derivatives, which could be prepared by Z-stereoselective 1,4-elimination with a-aryl diazoesters was successfully demonstrated. This successful regiospecific protocol enabled the preparation of the corresponding 1-amino- and 1-oxy-2-vinylcyclopropane derivatives as almost single stereoisomers.

  DOI：

  10.1055/s-0034-1380426
• 作为产物：
  描述：

  (E)-4-methoxybut-2-en-1-yl diisopropylcarbamate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以90%的产率得到(Z)-buta-1,3-dien-1-yl diisopropylcarbamate
  参考文献：
  名称：

  Copper-Catalyzed Regiospecific and 1,2-Regioselective Cyclopropanation of (1Z)-1-Amino- and (1Z)-1-Oxy-1,3-butadienyl Derivatives

  摘要：

  The copper-catalyzed regiospecific and 1,2-regioselective cyclopropanation of (1Z)-1-amino- and (1Z)-1-oxy-1,3-butadienyl derivatives, which could be prepared by Z-stereoselective 1,4-elimination with a-aryl diazoesters was successfully demonstrated. This successful regiospecific protocol enabled the preparation of the corresponding 1-amino- and 1-oxy-2-vinylcyclopropane derivatives as almost single stereoisomers.

  DOI：

  10.1055/s-0034-1380426

文献信息

• Sequential Homoaldolization. Cuprate Rearrangement in a Stereoselective Synthesis of Stannyl Dienes: Application to the Synthesis of the Western C10-C15 Subunit of (.+-.)-Tylosin Aglycon
  作者：Patrick Le Menez、Valerie Fargeas、Isabelle Berque、Jacques Poisson、Janick Ardisson、Jean-Yves Lallemand、Ange Pancrazi

  DOI：10.1021/jo00117a007

  日期：1995.6

  A stereospecific synthesis of stannyl diene 5, corresponding to the C10-C15 fragment of(+/-)-tylosin aglycon 2, was reported. Silyl carbamate 16, submitted to the Hoppe homoaldolization conditions with propanal, gave the anti aldol product 17 in 89% yield. Further treatment including oxidation of the silyl group led to lactone 21. The corresponding dihydrofuran 23 was then transformed into vinylstannane 25, via an efficient Kocienski rearrangement. An iodine exchange was performed on 25 and followed by a Stille coupling reaction with tributylstannyl acetylide. Stannyl cupration of the resulting silylated enyne 27 led in 44% yield to a 1:1 mixture of the desired (E,E)-stannyl diene 5b and the unexpected (E,Z) isomer 29. The same reaction performed on desilylated enyne 28 delivered in 85% yield the pure (E,E)-stannyl diene 5.
• Copper-Catalyzed Regiospecific and 1,2-Regioselective Cyclopropanation of (1Z)-1-Amino- and (1Z)-1-Oxy-1,3-butadienyl Derivatives
  作者：Eiji Tayama、Shun Saito

  DOI：10.1055/s-0034-1380426

  日期：——

  The copper-catalyzed regiospecific and 1,2-regioselective cyclopropanation of (1Z)-1-amino- and (1Z)-1-oxy-1,3-butadienyl derivatives, which could be prepared by Z-stereoselective 1,4-elimination with a-aryl diazoesters was successfully demonstrated. This successful regiospecific protocol enabled the preparation of the corresponding 1-amino- and 1-oxy-2-vinylcyclopropane derivatives as almost single stereoisomers.