2-[(E)-1-pentenyl]-3-methylmaleic anhydride | 240143-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 2-[(E)-1-pentenyl]-3-methylmaleic anhydride
• 英文别名: 3-methyl-4-[(E)-pent-1-enyl]furan-2,5-dione
• CAS: 240143-71-9
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: FHZWLUSSTOGXCU-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(E)-1-pentenyl]-3-methylmaleic anhydride 在 三乙胺 、 magnesium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以8.5%的产率得到(E)-(5R,6S,10aR)-10a-Methyl-5,6-dipropyl-5,6,10a,11-tetrahydro-4H-2,9-dioxa-dicyclopenta[a,d]cyclononene-1,3,8,10-tetraone
  参考文献：
  名称：

  Reinvestigation of the dimerisation process forming isoglaucanic acid

  摘要：

  The base catalysed dimerisation of 2-[(E)-1'-pentenyl]-3-methyl maleic anhydride has been extensively reinvestigated and the relative stereochemistry of an isoglaucanic acid derivative product has been determined by X-ray crystallography. The dimerisation process has been improved and the work up has been simplified, doubling the yield. Further co-products have been isolated and characterised from which a stepwise mechanism is proposed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00360-9
• 作为产物：
  描述：

  (E)-1-iodo-1-pentene 在 盐酸 、 sodium hydroxide 、 zinc dibromide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 18.75h， 生成 2-[(E)-1-pentenyl]-3-methylmaleic anhydride
  参考文献：
  名称：

  A Rapid Entry to Natural and Unnatural Disubstituted Maleic Anhydrides

  摘要：

  铜介导的乙炔二甲酸二甲酯的串联邻位双官能化反应，以及在某些情况下其中一个取代基的氧化反应，为获得各种天然和非天然的二取代马来酸酐提供了多用途的快速途径。

  DOI：

  10.1055/s-2002-25344

文献信息

• Progress toward a Biomimetic Synthesis of Phomoidride B
  作者：Gary A. Sulikowski、Weidong Liu、Fabio Agnelli、R. Michael Corbett、Zhushou Luo、Stefan J. Hershberger

  DOI：10.1021/ol025595c

  日期：2002.5.1

  [GRAPHIC]An intramolecular cyclization strategy for effecting a biomimetic synthesis of the core structure of the fungal secondary metabolites phomoidrides A and B is described. The cyclization substrate 20 is prepared in eight steps from dibromide 10. Treatment of 20 with triethylamine in acetonitrile results in a rapid cyclization to give 21 and 22 in good yield.
• A Rapid Entry to Natural and Unnatural Disubstituted Maleic Anhydrides
  作者：Robert M. Adlington、Jack E. Baldwin、Rhona J. Cox、Gareth J. Pritchard

  DOI：10.1055/s-2002-25344

  日期：——

  Copper-mediated tandem vicinal difunctionalisation of dimethyl acetylenedicarboxylate, followed in selected cases by oxidation of one of the substituents, provides a versatile and rapid route to a variety of natural and unnatural disubstituted maleic anhydrides.

  铜介导的乙炔二甲酸二甲酯的串联邻位双官能化反应，以及在某些情况下其中一个取代基的氧化反应，为获得各种天然和非天然的二取代马来酸酐提供了多用途的快速途径。
• Reinvestigation of the dimerisation process forming isoglaucanic acid
  作者：Jack E Baldwin、Andreas Beyeler、Rhona J Cox、Clare Keats、Gareth J Pritchard、Robert M Adlington、David J Watkin

  DOI：10.1016/s0040-4020(99)00360-9

  日期：1999.6

  The base catalysed dimerisation of 2-[(E)-1'-pentenyl]-3-methyl maleic anhydride has been extensively reinvestigated and the relative stereochemistry of an isoglaucanic acid derivative product has been determined by X-ray crystallography. The dimerisation process has been improved and the work up has been simplified, doubling the yield. Further co-products have been isolated and characterised from which a stepwise mechanism is proposed. (C) 1999 Elsevier Science Ltd. All rights reserved.

表征谱图