6-(buta-2,3-dienyl)-3-ethoxycyclohex-2-enone | 1010799-02-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(buta-2,3-dienyl)-3-ethoxycyclohex-2-enone
• CAS: 1010799-02-6
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: FZJOMKGPOFZZPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(buta-2,3-dienyl)-3-ethoxycyclohex-2-enone 、 [3-(1-methoxy-1-methyl-ethoxy)-prop-1-ynyl]-trimethylsilane 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.58h， 生成
  参考文献：
  名称：

  A General Synthetic Route to Differentially Functionalized Angularly and Linearly Fused [6−7−5] Ring Systems: A Rh(I)-Catalyzed Cyclocarbonylation Reaction

  摘要：

  Investigations of a Rh(I)-catalyzed cyclocarbonylation reaction reveal its general synthetic utility for accessing highly functionalized tricyclic [6-7-5] linear and angular ring systems from allene-ynes. Three types of allene-ynes were prepared and subjected to Rh(I)-catalyzed cyclocarbonylation conditions. For three series of allene-ynes, the [6-7-5] ring systems were afforded in varying yields depending on the substrate structure. One series of allene-ynes afforded the [6-6-5] ring system possessing an alpha-alkylidene cyclopentenone as a result of a selective reaction with the proximal double bond of the allene.

  DOI：

  10.1021/jo8007258
• 作为产物：
  描述：

  聚合甲醛 、 3-乙氧基-6-(丙-2-炔-1-基)环己-2-烯酮 在 二异丙胺 、 copper(I) bromide 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以77%的产率得到6-(buta-2,3-dienyl)-3-ethoxycyclohex-2-enone
  参考文献：
  名称：

  A General Synthetic Route to Differentially Functionalized Angularly and Linearly Fused [6−7−5] Ring Systems: A Rh(I)-Catalyzed Cyclocarbonylation Reaction

  摘要：

  Investigations of a Rh(I)-catalyzed cyclocarbonylation reaction reveal its general synthetic utility for accessing highly functionalized tricyclic [6-7-5] linear and angular ring systems from allene-ynes. Three types of allene-ynes were prepared and subjected to Rh(I)-catalyzed cyclocarbonylation conditions. For three series of allene-ynes, the [6-7-5] ring systems were afforded in varying yields depending on the substrate structure. One series of allene-ynes afforded the [6-6-5] ring system possessing an alpha-alkylidene cyclopentenone as a result of a selective reaction with the proximal double bond of the allene.

  DOI：

  10.1021/jo8007258

文献信息

• Mo(CO)₆- and [Rh(CO)₂Cl]₂-Catalyzed Allenic Cyclocarbonylation Reactions of Alkynones:  Efficient Access to Bicyclic Dienediones
  作者：Kay M. Brummond、Daitao Chen

  DOI：10.1021/ol702654x

  日期：2008.3.1

  Allenyl alkynones are efficiently transformed into fused bicyclic dienediones via cyclocarbonylation reaction conditions. Mo(CO)(6)/DMSO reaction conditions result in the formation of a bicyclo[3.3.0]octenone ring system, and the [Rh(CO)(2)Cl](2)-catalyzed reaction affords bicyclo[4.3.0]-nonenone and bicyclo[5.3.0]decenone scaffolds.