Methyl cis-6-<(phenylseleno)methyl>-1-(3-phenyl-2-propynyl)-3-cyclohexenecarboxylate

• 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: Methyl cis-6-<(phenylseleno)methyl>-1-(3-phenyl-2-propynyl)-3-cyclohexenecarboxylate
• 英文别名: methyl (1S,6S)-1-(3-phenylprop-2-ynyl)-6-(phenylselanylmethyl)cyclohex-3-ene-1-carboxylate
• 化学式: C₂₄H₂₄O₂Se
• 分子量: 423.413
• InChiKey: ASNDJTAKWIGQRG-QPPBQGQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  Methyl cis-6-<(phenylseleno)methyl>-1-(3-phenyl-2-propynyl)-3-cyclohexenecarboxylate 在 偶氮二异丁腈 、 三苯基氢化锡 作用下， 以 苯 为溶剂， 生成 Methyl (2Z,3aα,7aβ)-1,2,3,4,7,7a-hexahydro-2-(phenylmethylene)-3aH-indene-3a-carboxylate 、 Methyl (2E,3aα,7aβ)-1,2,3,4,7,7a-hexahydro-2-(phenylmethylene)-3aH-indene-3a-carboxylate
  参考文献：
  名称：

  Formation of trans ring-fused compounds by an alkylation-radical cyclization sequence

  摘要：

  Enolates derived from bicyclic lactones of type 1 (Scheme I) can be alkylated with 2-propynylic halides to give products 2, in which the unsaturated alkyl group is syn to the adjacent ring-fusion hydrogen. Reaction of 2 with sodium phenyl selenide and then with diazomethane produces esters 3, and these give trans ring-fused bicyclic compounds 4 when treated with triphenyltin hydride in the presence of a radical initiator. The bicyclic compounds afford ketones on double-bond cleavage, and the angular ester function can be converted into a methyl group. Similar processes occur if an aldehyde is used in the first step instead of a halide. The methodology is general.

  DOI：

  10.1021/jo00076a057
• 作为产物：
  描述：

  1-bromo-3-phenylprop-2-yne 在 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 14.5h， 生成 Methyl cis-6-<(phenylseleno)methyl>-1-(3-phenyl-2-propynyl)-3-cyclohexenecarboxylate
  参考文献：
  名称：

  Formation of trans ring-fused compounds by an alkylation-radical cyclization sequence

  摘要：

  Enolates derived from bicyclic lactones of type 1 (Scheme I) can be alkylated with 2-propynylic halides to give products 2, in which the unsaturated alkyl group is syn to the adjacent ring-fusion hydrogen. Reaction of 2 with sodium phenyl selenide and then with diazomethane produces esters 3, and these give trans ring-fused bicyclic compounds 4 when treated with triphenyltin hydride in the presence of a radical initiator. The bicyclic compounds afford ketones on double-bond cleavage, and the angular ester function can be converted into a methyl group. Similar processes occur if an aldehyde is used in the first step instead of a halide. The methodology is general.

  DOI：

  10.1021/jo00076a057

文献信息

• Formation of trans ring-fused compounds by an alkylation-radical cyclization sequence
  作者：Derrick L. J. Clive、Hartford W. Manning、Taryn L. B. Boivin、Maarten H. D. Postema

  DOI：10.1021/jo00076a057

  日期：1993.11

  Enolates derived from bicyclic lactones of type 1 (Scheme I) can be alkylated with 2-propynylic halides to give products 2, in which the unsaturated alkyl group is syn to the adjacent ring-fusion hydrogen. Reaction of 2 with sodium phenyl selenide and then with diazomethane produces esters 3, and these give trans ring-fused bicyclic compounds 4 when treated with triphenyltin hydride in the presence of a radical initiator. The bicyclic compounds afford ketones on double-bond cleavage, and the angular ester function can be converted into a methyl group. Similar processes occur if an aldehyde is used in the first step instead of a halide. The methodology is general.