(+/-)-2-phenyl-2-phenylsulfanyl-propionic acid ethyl ester | 42253-93-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (+/-)-2-phenyl-2-phenylsulfanyl-propionic acid ethyl ester
• 英文别名: (+/-)-2-Phenyl-2-phenylmercapto-propionsaeure-aethylester；2-Phenyl-2-phenylmercaptopropionsaeureaethylester；Ethyl 2-phenyl-2-phenylsulfanylpropanoate
• CAS: 42253-93-0；42253-94-1
• 化学式: C₁₇H₁₈O₂S
• 分子量: 286.395
• InChiKey: CBPKQLKJYWXXNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-2-phenyl-2-phenylsulfanyl-propionic acid ethyl ester 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (+/-)-2-Phenyl-2-phenylmercapto-propionsaeure
  参考文献：
  名称：

  Stereospecific Decarboxylative Allylation of Sulfones

  摘要：

  Allyl sulfonylacetic esters undergo highly stereospecific, palladium-catalyzed decarboxylative allylation. The reaction allows the stereospecific formation of tertiary homoallylic sulfones in high yield. In contrast to related reactions that proceed at -100 degrees C and require highly basic preformed organometallics, the decarboxylative coupling described herein occurs under mild nonbasic conditions and requires no stoichiometric additives. Allylation of the intermediate a-sulfonyl anion is more rapid than racemization, leading to a highly enantiospecific process. Density functional theory calculations indicate that the barrier for racemization is 9.9 kcal/mol, so the barrier for allylation must be <9.9 kcal/mol.

  DOI：

  10.1021/ja104196x
• 作为产物：
  描述：

  DL-阿卓乳酸半水物 在 五氯化磷 作用下， 生成 (+/-)-2-phenyl-2-phenylsulfanyl-propionic acid ethyl ester
  参考文献：
  名称：

  Stereochemical Paths of Reductive Desulfuration

  摘要：

  DOI：

  10.1021/ja01124a048

文献信息

• US4242519A
  申请人：——

  公开号：US4242519A

  公开（公告）日：1980-12-30
• US4278802A
  申请人：——

  公开号：US4278802A

  公开（公告）日：1981-07-14
• US4308208A
  申请人：——

  公开号：US4308208A

  公开（公告）日：1981-12-29
• Stereochemical Paths of Reductive Desulfuration
  作者：William A. Bonner

  DOI：10.1021/ja01124a048

  日期：1952.2
• Stereospecific Decarboxylative Allylation of Sulfones
  作者：Jimmie D. Weaver、Being J. Ka、David K. Morris、Ward Thompson、Jon A. Tunge

  DOI：10.1021/ja104196x

  日期：2010.9.8

  Allyl sulfonylacetic esters undergo highly stereospecific, palladium-catalyzed decarboxylative allylation. The reaction allows the stereospecific formation of tertiary homoallylic sulfones in high yield. In contrast to related reactions that proceed at -100 degrees C and require highly basic preformed organometallics, the decarboxylative coupling described herein occurs under mild nonbasic conditions and requires no stoichiometric additives. Allylation of the intermediate a-sulfonyl anion is more rapid than racemization, leading to a highly enantiospecific process. Density functional theory calculations indicate that the barrier for racemization is 9.9 kcal/mol, so the barrier for allylation must be <9.9 kcal/mol.