2,3-Dimethyl-6-(phenylsulfinyl)-1,8-nonadien-5-one | 131617-76-0

• 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: 2,3-Dimethyl-6-(phenylsulfinyl)-1,8-nonadien-5-one
• 英文别名: 6-(benzenesulfinyl)-2,3-dimethylnona-1,8-dien-5-one
• CAS: 131617-76-0；131682-59-2；131682-60-5；131682-61-6
• 化学式: C₁₇H₂₂O₂S
• 分子量: 290.426
• InChiKey: MAZVOUIYDWRNMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  20.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,3-Dimethyl-6-(phenylsulfinyl)-1,8-nonadien-5-one 在 copper diacetate 、 manganese triacetate 作用下， 以 溶剂黄146 为溶剂， 反应 22.0h， 生成 exo-(1S^*,5R^*)-4,5-Dimethyl-6-methylene-1(R^*)-(phenylsulfinyl)bicyclo<3.2.1>octan-2-one 、 endo-(1S^*,5R^*)-4,5-Dimethyl-6-methylene-1(R^*)-(phenylsulfinyl)bicyclo<3.2.1>octan-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
• 作为产物：
  描述：

  甲基苯基亚砜 在 sodium hydride 、 lithium diisopropyl amide 作用下， 反应 6.25h， 生成 2,3-Dimethyl-6-(phenylsulfinyl)-1,8-nonadien-5-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

• 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：——