2-cyclopentylidenemethylcyclohex-1-ene-1-carbaldehyde | 904744-68-9

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: 2-cyclopentylidenemethylcyclohex-1-ene-1-carbaldehyde
• 英文别名: 2-(Cyclopentylidenemethyl)cyclohexene-1-carbaldehyde；2-(cyclopentylidenemethyl)cyclohexene-1-carbaldehyde
• CAS: 904744-68-9
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: RZHIFOVLEJVIIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-cyclopentylidenemethylcyclohex-1-ene-1-carbaldehyde 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 生成 1-(2-cyclopentylidenemethyl-cyclohex-1-enyl)-prop-2-yn-1-ol
  参考文献：
  名称：

  Metal-Catalyzed Cycloisomerization of Enyne Functionalities via a 1,3-Alkylidene Migration

  摘要：

  We report a new metal-catalyzed 6-endo-dig cyclization of cis-4,6-dien-1-yn-3-ols, which produces substituted benzene and naphthalene derivatives with structural reorganization. In this process, we observe a 1,3-alkylidene migration via cleavage of the olefin double bond of the starting substrates. The ease and reliability of this cyclization are manifested by its compatibility with a wide array of diverse substrates and several pi-alkyne activators, including PtCl2, Zn(OTf)2, AuCl, and AuCl3.

  DOI：

  10.1021/ja062515h
• 作为产物：
  描述：

  2-溴-1-环己烯-1-甲醛 在 正丁基锂 、 叔丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 2-cyclopentylidenemethylcyclohex-1-ene-1-carbaldehyde
  参考文献：
  名称：

  Metal-Catalyzed Cycloisomerization of Enyne Functionalities via a 1,3-Alkylidene Migration

  摘要：

  We report a new metal-catalyzed 6-endo-dig cyclization of cis-4,6-dien-1-yn-3-ols, which produces substituted benzene and naphthalene derivatives with structural reorganization. In this process, we observe a 1,3-alkylidene migration via cleavage of the olefin double bond of the starting substrates. The ease and reliability of this cyclization are manifested by its compatibility with a wide array of diverse substrates and several pi-alkyne activators, including PtCl2, Zn(OTf)2, AuCl, and AuCl3.

  DOI：

  10.1021/ja062515h

文献信息

• Metal-Catalyzed Chemoselective Cycloisomerization of <i>cis</i>-2,4-Dien-1-als to 3-Cyclopentenones and 4-Alkylidene-3,4-dihydro-2<i>H</i>-pyrans
  作者：Ching-Yu Lo、Chung-Chang Lin、Hsin-Mei Cheng、Rai-Shung Liu

  DOI：10.1021/ol061248h

  日期：2006.7.1

  [GRAPHICS]PtCl2 (5 mol %) catalyst effected cycloisomerization of cis-2,4-dien-1-al (1) to 3-cyclopentenone (3) efficiently in hot toluene. In the presence of p-TSA, this PtCl2 catalysis gave 2-cyclopentenone (5) exclusively because of the secondary isomerization reaction. Although the 1-2 equilibrium state greatly favors aldehyde (1), PdCl2(PhCN)(2)(5 mol %) catalyzed cycloisomerization of aldehyde (1) to 4,6,7,8-tetrahydro-3H-isochromene (4) smoothly in hot toluene. A plausible mechanism is proposed on the basis of reaction observation and isotope-labeled experiment.