(3R)-3-[(E,2S)-4-diphenylphosphorylbut-3-en-2-yl]-2-methylcyclopentan-1-one | 131228-06-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R)-3-[(E,2S)-4-diphenylphosphorylbut-3-en-2-yl]-2-methylcyclopentan-1-one
• CAS: 131228-06-3；131321-10-3
• 化学式: C₂₂H₂₅O₂P
• 分子量: 352.413
• InChiKey: RSSDLKQPCRIGEG-QLVQEKPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  甲基环戊烯醇酮 、 苯基乙烯基砜 、 氧化膦,2-丁烯基二苯基-,(E)- 生成 (3R)-3-[(E,2S)-4-diphenylphosphorylbut-3-en-2-yl]-2-methylcyclopentan-1-one 、 (1RS,1'RS,2'E,3aSR,4SR,6SR,7aRS)-7a-methyl-1-<1'-methyl-3'-(diphenylphosphinoyl)prop-2'-enyl>-4,6-bis(phenylsulfonyl)octahydro-1H-inden-3a-ol
  参考文献：
  名称：

  Novel formation of isomeric bicyclo[3.2.0]heptan-1-ols from phenyl vinyl sulfoxide and the cyclopentanone lithium enolate generated by conjugate addition of lithiated (E)-but-2-enyldiphenylphosphine oxide to 2-methylcyclopent-2-enone

  摘要：

  Whereas the title enolate 2 in THF reacts at -10-degrees-C with 2 equiv of phenyl vinyl sulfone to provide the hydrindanol 9 (9%), it reacts with 1 equiv of phenyl vinyl sulfoxide to give 7-(phenylsulfinyl)bicyclo[3.2.0]heptan-1-ol sulfoxides 11 and 12 (50% overall) and adduct 10 (10%). The yield of the bicycloheptanols decreases to 35% in the dark and increases to 68% under irradiation. Their formation is entirely suppressed by HMPA. Stereochemistry of 12 was provided by X-ray crystallography of the derived sulfone 14. Base-induced ring opening of the sulfone in the presence of phenyl vinyl sulfone gives the alkylated cyclopentanones 17, 18, and 21 and the bicyclo[2.2.1]heptanone 20. The bicyclo[3.2.0]heptanols 11 and 12 are considered to arise by intramolecular nucleophilic or single electron transfer processes.

  DOI：

  10.1021/jo00020a018