2-(2-Methyl-allyl)-2-pent-4-enyl-malonic acid diethyl ester | 197155-13-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-(2-Methyl-allyl)-2-pent-4-enyl-malonic acid diethyl ester
• 英文别名: Diethyl 2-(2-methylprop-2-enyl)-2-pent-4-enylpropanedioate
• CAS: 197155-13-8
• 化学式: C₁₆H₂₆O₄
• 分子量: 282.38
• InChiKey: WHOBZCRMULMVSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-Methyl-allyl)-2-pent-4-enyl-malonic acid diethyl ester 在 (C(CH₃)(CF₃)2O)2Mo(=N-2,6-(i-Pr)2-Ph)=CH-CPh(CH₃)2 作用下， 以 苯 为溶剂， 以96%的产率得到4-Methyl-cyclohept-3-ene-1,1-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Effects of Olefin Substitution on the Ring-Closing Metathesis of Dienes

  摘要：

  Ruthenium alkylidene 1 and molybdenum alkylidene 2 have been utilized in the ring-closing metathesis (RCM) of dienes containing gem-disubstituted olefins to yield td-and tetrasubstituted cyclic olefins. Dienes with sterically demanding and/or electron-withdrawing substituents such as Ph, CO2Me, and Bu-t were cyclized successfully with 2, but did not cyclize with 1. Tetrasubstituted cyclic olefins could be formed with 2, but not using alkylidene-1. Dienes with allylic functional groups yielded functionalized cyclic olefins when treated with 1.

  DOI：

  10.1021/jo970877p
• 作为产物：
  描述：

  5-溴-1-戊烯 在 sodium ethanolate 作用下， 生成 2-(2-Methyl-allyl)-2-pent-4-enyl-malonic acid diethyl ester
  参考文献：
  名称：

  Effects of Olefin Substitution on the Ring-Closing Metathesis of Dienes

  摘要：

  Ruthenium alkylidene 1 and molybdenum alkylidene 2 have been utilized in the ring-closing metathesis (RCM) of dienes containing gem-disubstituted olefins to yield td-and tetrasubstituted cyclic olefins. Dienes with sterically demanding and/or electron-withdrawing substituents such as Ph, CO2Me, and Bu-t were cyclized successfully with 2, but did not cyclize with 1. Tetrasubstituted cyclic olefins could be formed with 2, but not using alkylidene-1. Dienes with allylic functional groups yielded functionalized cyclic olefins when treated with 1.

  DOI：

  10.1021/jo970877p

文献信息

• Catalytic and Structural Studies of Hoveyda-Grubbs Type Pre-Catalysts Bearing Modified Ether Ligands
  作者：Stefano Guidone、Enguerrand Blondiaux、Cezary Samojłowicz、Łukasz Gułajski、Mariusz Kędziorek、Maura Malińska、Aleksandra Pazio、Krzysztof Woźniak、Karol Grela、Angelino Doppiu、Catherine S. J. Cazin

  DOI：10.1002/adsc.201200385

  日期：2012.10.8

  Catalytic and crystallographic studies of Hoveyda–Grubbs type pre-catalysts M51TM and M52TM were performed. These two new instruments in the olefin metathesis catalyst toolbox were shown to be active at ambient temperature and at low loading, leading to clean formation of ring-closing, ring-closing enyne and cross metathesis products.

  进行了Hoveyda-Grubbs型预催化剂M51 TM和M52 TM的催化和晶体学研究。烯烃复分解催化剂工具箱中的这两种新仪器显示在室温和低负荷下具有活性，从而导致闭环，闭环烯炔和交叉复分解产物的清洁形成。
• Rendering Schrock-type Molybdenum Alkylidene Complexes Air Stable: User-Friendly Precatalysts for Alkene Metathesis
  作者：Johannes Heppekausen、Alois Fürstner

  DOI：10.1002/anie.201102012

  日期：2011.8.16

  A matter of convenience: Schrock molybdenum alkylidenes are amongst the most powerful olefin metathesis catalysts known to date, but their sensitivity to air and moisture mandates their handling in a glove‐box or by Schlenk techniques. This inconvenience is circumvented by using the corresponding phenanthroline‐ or bipyridine adducts, which are bench‐stable and hence very user‐friendly. The active

  方便的问题：Schrock钼亚烷基是迄今为止已知最强大的烯烃复分解催化剂之一，但它们对空气和湿气的敏感性要求它们在手套箱中或通过Schlenk技术进行处理。使用相应的菲咯啉或联吡啶加合物可以避免这种不便，它们是稳定的，因此非常易于使用。在甲苯中用ZnCl 2处理时，活性物质可以毫不妥协的形式从这些预催化剂中释放出来（参见方案）。
• Effects of Olefin Substitution on the Ring-Closing Metathesis of Dienes
  作者：Thomas A. Kirkland、Robert H. Grubbs

  DOI：10.1021/jo970877p

  日期：1997.10.1

  Ruthenium alkylidene 1 and molybdenum alkylidene 2 have been utilized in the ring-closing metathesis (RCM) of dienes containing gem-disubstituted olefins to yield td-and tetrasubstituted cyclic olefins. Dienes with sterically demanding and/or electron-withdrawing substituents such as Ph, CO2Me, and Bu-t were cyclized successfully with 2, but did not cyclize with 1. Tetrasubstituted cyclic olefins could be formed with 2, but not using alkylidene-1. Dienes with allylic functional groups yielded functionalized cyclic olefins when treated with 1.