(2S,3S)-2,5-Bis-(2-benzenesulfinyl-ethyl)-3-[(E)-(R)-3-(diphenyl-phosphinoyl)-1-methyl-allyl]-2-methyl-cyclopentanone | 135455-41-3

• 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: (2S,3S)-2,5-Bis-(2-benzenesulfinyl-ethyl)-3-[(E)-(R)-3-(diphenyl-phosphinoyl)-1-methyl-allyl]-2-methyl-cyclopentanone
• CAS: 135455-41-3
• 化学式: C₃₈H₄₁O₄PS₂
• 分子量: 656.847
• InChiKey: UEOZALCPVMRAKF-SETNETBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.76
• 重原子数：
  45.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  68.28
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2,5-Bis-(2-benzenesulfinyl-ethyl)-3-[(E)-(R)-3-(diphenyl-phosphinoyl)-1-methyl-allyl]-2-methyl-cyclopentanone 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到(1'RS,2RS,2'E,3SR,5RS/SR)-2-Methyl-3-<1'-methyl-3'-(diphenylphosphinoyl)prop-2'-enyl>-2,5-bis<2''-(phenylsulfonyl)ethyl>cyclopentan-1-one
  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
• 作为产物：
  描述：

  甲基环戊烯醇酮 、 苯基乙烯基亚砜 、 氧化膦,2-丁烯基二苯基-,(E)- 生成 (2S,3S)-2,5-Bis-(2-benzenesulfinyl-ethyl)-3-[(E)-(R)-3-(diphenyl-phosphinoyl)-1-methyl-allyl]-2-methyl-cyclopentanone 、 (2R,3R)-2,5,5-Tris-(2-benzenesulfinyl-ethyl)-3-[(E)-(S)-3-(diphenyl-phosphinoyl)-1-methyl-allyl]-2-methyl-cyclopentanone 、 (1RS,1'RS,2'E,4RS,5RS,7RS)-5-methyl-4-<1'-methyl-3'-(diphenylphosphinoyl)prop-2'-enyl>-7-(phenylsulfinyl)bicyclo<3.2.0>heptan-1-ol 、 (1RS,1'RS,2'E,4RS,5RS,7SR)-5-methyl-4-<1'-methyl-3'-(diphenylphosphinoyl)prop-2'-enyl>-7-(phenylsulfinyl)bicyclo<3.2.0>heptan-1-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