(E)-tert-butyl buta-1,3-dien-1-yl(phenyl)carbamate | 1609118-07-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-tert-butyl buta-1,3-dien-1-yl(phenyl)carbamate
• 英文别名: tert-butyl (E)-buta-1,3-dien-1-yl(phenyl)carbamate；tert-butyl N-[(1E)-buta-1,3-dienyl]-N-phenylcarbamate
• CAS: 1609118-07-1
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: XJQXMNVHRPALAG-WUXMJOGZSA-N

物化性质

• 沸点：
  335.3±15.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  (E)-tert-butyl buta-1,3-dien-1-yl(phenyl)carbamate 、 2-二氮杂-2-(4-甲基苯基)乙酸甲酯 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以77%的产率得到rel-(1S,2R)-methyl 2-((E)-2-((tert-butoxycarbonyl)(phenyl)amino)vinyl)-1-(p-tolyl)cyclopropanecarboxylate
  参考文献：
  名称：

  Copper(II)–acid catalyzed cyclopropanation of 1,3-dienamides by electrophilic activation of α-aryl diazoesters

  摘要：

  Copper(II)-acid catalyzed cyclopropanation of electron-rich alkenes, such as 1,3-dienamides, with cc-aryl diazoesters are described. The reaction could be performed without rare metal catalysts, excess substrate, or the need for the slow addition of the diazoesters. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.03.115
• 作为产物：
  描述：

  (Z)-tert-butyl (4-methoxybut-2-en-1-yl)(phenyl)carbamate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以94%的产率得到(E)-tert-butyl buta-1,3-dien-1-yl(phenyl)carbamate
  参考文献：
  名称：

  Stereoselective preparation of (1Z)- and (1E)-N-Boc-1-amino-1,3-dienes by stereospecific base-promoted 1,4-elimination

  摘要：

  The base-promoted 1,4-elimination reaction of N-Boc-1-amino-4-methoxy-2-alkene 1 is shown to proceed with perfect stereoselectivity to afford the corresponding N-Boc-1-amino-1,3-diene 2 in good yields. The reaction is highly stereospecific. The substrate E-1 gave 1Z-2 by the 'Syn-Effect' and Z-1 gave 1E-2 via formation of a chelated intermediate. Our method is widely applicable to the preparation of various types of N-Boc-1-amino-1,3-dienes 2. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.12.039

文献信息

• 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.