(E)-4-methoxybut-2-en-1-ol | 22427-04-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-4-methoxybut-2-en-1-ol
• 英文别名: 4-methoxybut-2-en-1-ol；4-methoxy-but-2t-en-1-ol；4-methoxy-2-butene-1-ol；trans-4-Methoxy-2-buten-1-ol
• CAS: 22427-04-9
• 化学式: C₅H₁₀O₂
• 分子量: 102.133
• InChiKey: JWAVFTBBSAZCCU-NSCUHMNNSA-N

物化性质

• 沸点：
  156.9±28.0 °C(Predicted)
• 密度：
  0.940±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4-methoxybut-2-en-1-ol 在 三溴化磷 作用下， 以 乙醚 为溶剂， 反应 0.33h， 以539 mg的产率得到反式-1-溴-4-甲氧基-2-丁烯
  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：

  4-methoxy-but-2-yn-1-ol 在 红铝 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 2.0h， 以1.48g的产率得到(E)-4-methoxybut-2-en-1-ol
  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

• Method of intercoversion of enantiomers of acyclic
  申请人：Eastman Kodak Company

  公开号：US05250743A1

  公开（公告）日：1993-10-05

  In accordance with the present invention, a method for the interconvertion of the enantiomers of acyclic 1,2-dihydroxy-3-alkenes or for converting either enantiomer of acylic 1,2-dihydroxy-3-alkenes to the corresponding antipodal 1-hydroxy-2-alkoxy-3-alkene compounds has been discovered, comprising reacting in an acidic reaction media either enantiomer of an acylic vinyl epoxide (which can be derived from the corresponding acyclic 1,2-dihydroxy-3-alkene) with water, alcohol, or a mixture thereof. When substantially optically pure acyclic vinyl epoxide compounds are employed in the inventive method, the interconverted acyclic 1,2-dihydroxy-3-alkene or 1-hydroxy-2-alkoxy-3-alkene compound products are also substantially optically pure.

  根据本发明，发现了一种用于互变无环1,2-双羟基-3-烯烃对映体或将无环1,2-双羟基-3-烯烃的任一对映体转化为相应的对映异构体1-羟基-2-烷氧基-3-烯烃化合物的方法，包括在酸性反应介质中反应无环乙烯环氧化物的任一对映体（可以由相应的无环1,2-双羟基-3-烯烃衍生）与水、醇或其混合物。当使用基本上光学纯的无环乙烯环氧化合物进行本发明的方法时，互变的无环1,2-双羟基-3-烯烃或1-羟基-2-烷氧基-3-烯烃化合物产物也基本上是光学纯的。
• 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.
• Regioselective synthesis of secondary 1,3-dienamides by successive eliminations
  作者：Eiji Tayama、Shun Saito

  DOI：10.1016/j.tet.2015.11.065

  日期：2016.2

  The regioselective synthesis of secondary 1,3-dienamides 3 (1-N-acylamino-1,3-dienes) is successfully demonstrated by regiospecific base -promoted 1,4 -elimination of (Z)- or (E)-N,N-di-Boc-4-methoxy-2-buten-1 -ylamine 1 followed by mono-Boc elimination in situ. (C) 2015 Elsevier Ltd. All rights reserved,
• Electroorganic chemistry. 68. A new method of 1,4-transposition of a carbonyl group
  作者：Tatsuya Shono、Shigenori Kashimura

  DOI：10.1021/jo00159a042

  日期：1983.6
• [2,3]-Wittig rearrangement of methyl β-pyrrolidinyl-γ-allyloxy-(E)-2-butenoate. Expeditious synthesis of 5-alkenyl-4-pyrrolidin-1-yl-5H-furan-2-ones
  作者：Yu-Jang Li、Pei-Ting Lee、Chuen-Mei Yang、Yuan-Kang Chang、Ying-Chieh Weng、Yi-Hung Liu

  DOI：10.1016/j.tetlet.2004.01.013

  日期：2004.2

  Dienolates of various gamma-allyloxy substituted methyl beta-pyrrolidinyl (E)-2-butenoate undergo a [2,3]-Wittig rearrangement to generate various 5-alkenyl-4-pyrrolidin-1-yl-5H-furan-2-one type compounds. (C) 2004 Elsevier Ltd. All rights reserved.