(E)-tert-butyl (4-methoxybut-2-en-1-yl)(phenyl)carbamate | 1609118-16-2

• 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 (4-methoxybut-2-en-1-yl)(phenyl)carbamate
• 英文别名: tert-butyl N-[(E)-4-methoxybut-2-enyl]-N-phenylcarbamate
• CAS: 1609118-16-2
• 化学式: C₁₆H₂₃NO₃
• 分子量: 277.364
• InChiKey: LMQWYHDUPMFDCS-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-tert-butyl (4-methoxybut-2-en-1-yl)(phenyl)carbamate 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 以74%的产率得到(Z)-tert-butyl buta-1,3-dien-1-yl(phenyl)carbamate
  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-ol 在 三溴化磷 、 sodium hydride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.33h， 生成 (E)-tert-butyl (4-methoxybut-2-en-1-yl)(phenyl)carbamate
  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

文献信息

• Stereoselective preparation of (1Z)- and (1E)-N-Boc-1-amino-1,3-dienes by stereospecific base-promoted 1,4-elimination
  作者：Eiji Tayama、Yuka Toma

  DOI：10.1016/j.tet.2014.12.039

  日期：2015.1

  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.