2-(2'-Carbethoxyvinyl)-2-(3'-prop-1'-ynyl)cyclohexanone | 151813-17-1

• 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'-Carbethoxyvinyl)-2-(3'-prop-1'-ynyl)cyclohexanone
• 英文别名: ethyl (E)-3-(2-oxo-1-prop-2-ynylcyclohexyl)prop-2-enoate
• CAS: 151813-17-1
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: IKXFNKPKEXLOPL-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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-(2'-Carbethoxyvinyl)-2-(3'-prop-1'-ynyl)cyclohexanone 在 palladium on barium sulfate 氢气 作用下， 以 吡啶 为溶剂， 反应 0.33h， 生成 2-(3'-Prop-1'-enyl)-2-(2'-carbethoxyvinyl)cyclohexanone
  参考文献：
  名称：

  Stereocontrolled synthesis of angularly fused tricyclic systems by tin-mediated radical cyclization

  摘要：

  Two efficient pathways for the stereocontrolled synthesis of functionalized, angularly fused tricyclic carbocycles from readily available 2-formylcycloalkanones are described. Tricyclo[7.4.0.0(4,9)]tridecane 13, tricyclo[7.5.0.0(4,9)]tetradecane 16, and tricyclo[7.3.0.0(4,9)]dodecanes 20 and 21 were synthesized by means of path A. Path B is highly convergent, is 95% stereoselective, and leads to a tricyclo-[7.4.0.0(4,9)]tridecane skeleton 29.

  DOI：

  10.1021/jo00079a023
• 作为产物：
  描述：

  2-(羟基亚甲基)环己酮 在 potassium tert-butylate 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 2.5h， 生成 2-(2'-Carbethoxyvinyl)-2-(3'-prop-1'-ynyl)cyclohexanone
  参考文献：
  名称：

  Stereocontrolled synthesis of angularly fused tricyclic systems by tin-mediated radical cyclization

  摘要：

  Two efficient pathways for the stereocontrolled synthesis of functionalized, angularly fused tricyclic carbocycles from readily available 2-formylcycloalkanones are described. Tricyclo[7.4.0.0(4,9)]tridecane 13, tricyclo[7.5.0.0(4,9)]tetradecane 16, and tricyclo[7.3.0.0(4,9)]dodecanes 20 and 21 were synthesized by means of path A. Path B is highly convergent, is 95% stereoselective, and leads to a tricyclo-[7.4.0.0(4,9)]tridecane skeleton 29.

  DOI：

  10.1021/jo00079a023

文献信息

• Synthesis of functionalised bicyclo[4.4.0] and spiro [5.4] compounds by tin-mediated radical cyclization
  作者：Ponnusamy Shanmugam、Rajagopal Srinivasan、Krishnamoorthy Rajagopalan

  DOI：10.1016/s0040-4020(97)00735-7

  日期：1997.8

  Functionalised bicyclo[4.4.0] system 5, and spiro[5.4] system 10 were synthesised from the bispropargyl compound 3 and the monopropargyl compound 6 by tin-mediated radical cyclization. (C) 1997 Elsevier Science Ltd.