Methyl cis-1-(2-hexynyl)-2-<(phenylseleno)methyl>cyclopentanecarboxylate | 130100-26-4

• 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-1-(2-hexynyl)-2-<(phenylseleno)methyl>cyclopentanecarboxylate
• 英文别名: methyl (1R,2R)-1-hex-2-ynyl-2-(phenylselanylmethyl)cyclopentane-1-carboxylate
• CAS: 130100-26-4
• 化学式: C₂₀H₂₆O₂Se
• 分子量: 377.385
• InChiKey: JSZYUDNEHSENQY-PXNSSMCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 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-1-(2-hexynyl)-2-<(phenylseleno)methyl>cyclopentanecarboxylate 在 偶氮二异丁腈 、 三苯基氢化锡 作用下， 以 苯 为溶剂， 以14%的产率得到
  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：

  hexahydro-cyclopenta[c]furan-1-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醚 为溶剂， 生成 Methyl cis-1-(2-hexynyl)-2-<(phenylseleno)methyl>cyclopentanecarboxylate
  参考文献：
  名称：

  自由基环化法构建反式环稠合化合物

  摘要：

  用丙-2-炔（和烯丙基）溴化物将衍生自（4）型双环内酯的烯醇化物烷基化，得到产物（5），其中不饱和烷基与剩余的环稠合氢同构；丙-2- ynylic醛类可以被用来代替卤化物，并且在这两种情况下，内酯开与苯基硒化钠，酯化和治疗与锡烷然后导致反形环稠合的双环化合物。

  DOI：

  10.1039/c39900000972

文献信息

• Construction of trans-ring-fused compounds by radical cyclızation
  作者：Derrick L. J. Clive、Hartford W. Manning、Taryn L. B. Boivin

  DOI：10.1039/c39900000972

  日期：——

  hydrogen; prop-2-ynylic aldehydes can be used instead of halides and, in both cases, lactone opening with sodium phenyl selenide, esterification, and treatment with a stannane then leads to trans-ring-fused bicyclic compounds.

  用丙-2-炔（和烯丙基）溴化物将衍生自（4）型双环内酯的烯醇化物烷基化，得到产物（5），其中不饱和烷基与剩余的环稠合氢同构；丙-2- ynylic醛类可以被用来代替卤化物，并且在这两种情况下，内酯开与苯基硒化钠，酯化和治疗与锡烷然后导致反形环稠合的双环化合物。
• 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.