3-Isopropenyl-3-methyl-cyclobut-1-ene-1,2-dicarboxylic acid dimethyl ester | 283156-23-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-Isopropenyl-3-methyl-cyclobut-1-ene-1,2-dicarboxylic acid dimethyl ester
• 英文别名: Dimethyl 3-methyl-3-prop-1-en-2-ylcyclobutene-1,2-dicarboxylate
• CAS: 283156-23-0
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: SRONNEJFRHQXCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  3-Isopropenyl-3-methyl-cyclobut-1-ene-1,2-dicarboxylic acid dimethyl ester 在 bis(triphenylphosphine)nickel(II) chloride 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 dimethyl 4,5-dimethylcyclohexa-1,4-diene-1,2-dicarboxylate
  参考文献：
  名称：

  The ring expansion of a dimethyl-substituted vinylcyclobutene derivative by metal complexes that can undergo an inner-sphere electron transfer

  摘要：

  The ring expansion of a dimethyl-substituted vinylcyclobutene derivative to the corresponding dimethyl-substituted cyclohexadiene or aromatic compound was studied. It was found that metal complexes of Ni(I), Ti(III), Sm(II), and Fe(II), which can undergo an inner-sphere electron-transfer reaction, allow the rearrangement to occur at room temperature. Other oxidation states of these metals and complexes that can only undergo an outer-sphere electron-transfer process do not promote this ring expansion reaction. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00054-1
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 锌 作用下， 以 1,4-二氧六环 、 正己烷 为溶剂， 反应 24.0h， 以69%的产率得到3-Isopropenyl-3-methyl-cyclobut-1-ene-1,2-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  The rearrangement of 3-vinylcyclobutene derivatives promoted by metallic Lewis acids

  摘要：

  The rearrangement of 3-vinylcyclobutene derivatives in the presence of metallic Lewis acids is discussed. Although most of the Lewis acids tried were too weak to cause any chemistry to occur, WCl6 and AlCl3 promote an interesting isomerization reaction. Especially significant is, for the first time, starting with a vinylcyclobutene, a product with a five-membered ring rather than a six-membered ring was obtained. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(02)01585-1

文献信息

• The ring expansion of a dimethyl-substituted vinylcyclobutene derivative by metal complexes that can undergo an inner-sphere electron transfer
  作者：Herman L Holt、Tom Russo、Allan R Pinhas

  DOI：10.1016/s0022-328x(00)00054-1

  日期：2000.4

  The ring expansion of a dimethyl-substituted vinylcyclobutene derivative to the corresponding dimethyl-substituted cyclohexadiene or aromatic compound was studied. It was found that metal complexes of Ni(I), Ti(III), Sm(II), and Fe(II), which can undergo an inner-sphere electron-transfer reaction, allow the rearrangement to occur at room temperature. Other oxidation states of these metals and complexes that can only undergo an outer-sphere electron-transfer process do not promote this ring expansion reaction. (C) 2000 Elsevier Science S.A. All rights reserved.
• The rearrangement of 3-vinylcyclobutene derivatives promoted by metallic Lewis acids
  作者：Martin A Lovchik、Allan R Pinhas

  DOI：10.1016/s0022-328x(02)01585-1

  日期：2002.8

  The rearrangement of 3-vinylcyclobutene derivatives in the presence of metallic Lewis acids is discussed. Although most of the Lewis acids tried were too weak to cause any chemistry to occur, WCl6 and AlCl3 promote an interesting isomerization reaction. Especially significant is, for the first time, starting with a vinylcyclobutene, a product with a five-membered ring rather than a six-membered ring was obtained. (C) 2002 Elsevier Science B.V. All rights reserved.