1-(Phenylsulfinyl)-5-hexen-2-one | 51620-81-6

• 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: 1-(Phenylsulfinyl)-5-hexen-2-one
• 英文别名: 1-(benzenesulfinyl)hex-5-en-2-one
• CAS: 51620-81-6
• 化学式: C₁₂H₁₄O₂S
• 分子量: 222.308
• InChiKey: PTVULAADDZWCGX-UHFFFAOYSA-N

物化性质

• 沸点：
  386.8±25.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(Phenylsulfinyl)-5-hexen-2-one 生成 4-(Phenylsulfinyl)-1,8-nonadien-5-one
  参考文献：
  名称：

  SNIDER, BARRY B.;WAN, BARBARA YU-FONG;BUCKMAN, BRAD O.;FOXMAN, BRUCE M., J. ORG. CHEM., 56,(1991) N, C. 328-334

  摘要：

  DOI：
• 作为产物：
  描述：

  4-戊烯酸乙酯 、 甲基苯基亚砜 在 lithium diisopropyl amide 作用下， 生成 1-(Phenylsulfinyl)-5-hexen-2-one
  参考文献：
  名称：

  Manganese(III)-based asymmetric oxidative free-radical cyclization of unsaturated .beta.-keto sulfoxides

  摘要：

  beta-Keto sulfoxides and beta-keto sulfones can be used as substrates for Mn(III)- and Cu(II)-based oxidative free-radical cyclizations. The sulfoxide chiral center completely controls the stereochemistry of the cyclization. Oxidative cyclization of racemic sulfoxide 8 affords 13 as a single diastereomer. Oxidative cyclization of enantiomerically pure sulfoxide 20 gives 21 as a single enantiomer. The chiral auxiliary can be removed by oxidation with potassium peroxomonosulfate to give the sulfone followed by reduction with sodium amalgam to give bicyclo[3.2.1]octanone 23. Oxidative cyclization of 26 gives indanone 29, which spontaneously loses toluenesulfenic acid to give indenone 30.

  DOI：

  10.1021/jo00001a061

文献信息

• Facile formation of 4-hydroxyalk-2-enone functionality
  作者：Junzo Nokami、Akira Nishimura、Masaru Sunami、Shoji Wakabayashi

  DOI：10.1016/s0040-4039(00)95803-9

  日期：1987.1
• SNIDER, BARRY B.;WAN, BARBARA YU-FONG;BUCKMAN, BRAD O.;FOXMAN, BRUCE M., J. ORG. CHEM., 56,(1991) N, C. 328-334
  作者：SNIDER, BARRY B.、WAN, BARBARA YU-FONG、BUCKMAN, BRAD O.、FOXMAN, BRUCE M.

  DOI：——

  日期：——
• NOKAMI JUNZO; NISHIMURA AKIRA; SUNAMI MASARU; WAKABAYASHI SHOJI, TETRAHEDRON LETT., 28,(1987) N 6, 649-650
  作者：NOKAMI JUNZO、 NISHIMURA AKIRA、 SUNAMI MASARU、 WAKABAYASHI SHOJI

  DOI：——

  日期：——
• Manganese(III)-based asymmetric oxidative free-radical cyclization of unsaturated .beta.-keto sulfoxides
  作者：Barry B. Snider、Barbara Yu Fong Wan、Brad O. Buckman、Bruce M. Foxman

  DOI：10.1021/jo00001a061

  日期：1991.1

  beta-Keto sulfoxides and beta-keto sulfones can be used as substrates for Mn(III)- and Cu(II)-based oxidative free-radical cyclizations. The sulfoxide chiral center completely controls the stereochemistry of the cyclization. Oxidative cyclization of racemic sulfoxide 8 affords 13 as a single diastereomer. Oxidative cyclization of enantiomerically pure sulfoxide 20 gives 21 as a single enantiomer. The chiral auxiliary can be removed by oxidation with potassium peroxomonosulfate to give the sulfone followed by reduction with sodium amalgam to give bicyclo[3.2.1]octanone 23. Oxidative cyclization of 26 gives indanone 29, which spontaneously loses toluenesulfenic acid to give indenone 30.