(+)-(R)-Methyl 3,5-dioxo-6-(p-tolylsulfinyl)hexanoate | 171523-66-3

• 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: (+)-(R)-Methyl 3,5-dioxo-6-(p-tolylsulfinyl)hexanoate
• 英文别名: methyl 6-[(R)-(4-methylphenyl)sulfinyl]-3,5-dioxohexanoate
• CAS: 171523-66-3
• 化学式: C₁₄H₁₆O₅S
• 分子量: 296.344
• InChiKey: HODYVBIMPMDEGT-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  96.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-(R)-Methyl 3,5-dioxo-6-(p-tolylsulfinyl)hexanoate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以45%的产率得到(+)-<5(S),S(R)> methyl 3-oxo-5-hydroxy-6-(p-tolylsulfinyl) hexanoate
  参考文献：
  名称：

  Enantioselective synthesis of a bicyclic ketal induced by chiral sulfoxides: (−)-(1R, 3R, 5S)-endo-1,3-dimethyl-2,9-dioxabicyclo-[3,3,1]-nonane

  摘要：

  The bicyclic ketal, (-)-(1R,3R,5S)-1,3-dimethyl-2,9-dioxabicyclo-[3,3,1]-nonane, was prepared by a short enantioselective reduction of an enantiomerically pure beta,delta-diketosulfoxide.

  DOI：

  10.1016/0957-4166(95)00356-t
• 作为产物：
  描述：

  3,5-二酮己酸甲酯 、 (-)-menthyl p-toluenesulfinate 在 正丁基锂 、 sodium hydride 作用下， 生成 (+)-(R)-Methyl 3,5-dioxo-6-(p-tolylsulfinyl)hexanoate
  参考文献：
  名称：

  Enantioselective synthesis of a bicyclic ketal induced by chiral sulfoxides: (−)-(1R, 3R, 5S)-endo-1,3-dimethyl-2,9-dioxabicyclo-[3,3,1]-nonane

  摘要：

  The bicyclic ketal, (-)-(1R,3R,5S)-1,3-dimethyl-2,9-dioxabicyclo-[3,3,1]-nonane, was prepared by a short enantioselective reduction of an enantiomerically pure beta,delta-diketosulfoxide.

  DOI：

  10.1016/0957-4166(95)00356-t

文献信息

• PROCEDE DE PREPARATION DE COMPOSES A GROUPEMENT BETA-HYDROXY-DELTA-LACTONE ANALOGUES DE LA (+) COMPACTINE ET DE LA (+) MEVINOLINE
  申请人：L'OREAL

  公开号：EP0805800B1

  公开（公告）日：2001-03-14
• Enantioselective synthesis of a bicyclic ketal induced by chiral sulfoxides: (−)-(1R, 3R, 5S)-endo-1,3-dimethyl-2,9-dioxabicyclo-[3,3,1]-nonane
  作者：Guy Solladié、Nathalie Huser

  DOI：10.1016/0957-4166(95)00356-t

  日期：1995.11

  The bicyclic ketal, (-)-(1R,3R,5S)-1,3-dimethyl-2,9-dioxabicyclo-[3,3,1]-nonane, was prepared by a short enantioselective reduction of an enantiomerically pure beta,delta-diketosulfoxide.
• Chiral Sulfoxides in Asymmetric Synthesis: Enantioselective Synthesis of the Lactonic Moiety of (+)-Compactin and (+)-Mevinolin. Application to a Compactin Analog
  作者：Guy Solladie、Claude Bauder、Leucio Rossi

  DOI：10.1021/jo00129a018

  日期：1995.12

  The lactonic part of (+)-compactin and (+)-mevinolin as well as a compactin analogue were synthesized in an enantioselective way from a beta,delta-diketo sulfoxide easily obtained by the reaction of the trianion of methyl 3,5-dioxohexanoate with (-)-menthyl (S)-p-toluenesulfinate. The main reaction was the two-step stereoselective reduction of beta,delta-diketo sulfoxide without any protective group.