(+/-)-Methyl (2-naphthylsulfinyl)acetate | 138331-42-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+/-)-Methyl (2-naphthylsulfinyl)acetate
• 英文别名: Methyl 2-naphthalen-2-ylsulfinylacetate
• CAS: 138331-42-7
• 化学式: C₁₃H₁₂O₃S
• 分子量: 248.302
• InChiKey: QBFQUXOKUTVBGU-UHFFFAOYSA-N

物化性质

• 沸点：
  447.6±28.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-Methyl (2-naphthylsulfinyl)acetate 在 水 作用下， 以 甲苯 为溶剂， 反应 27.0h， 生成 (+)-(naphthalene-2-sulfinyl)-acetic acid 、 (S)-(-)-(2-Naphthylsulfinyl)acetic acid
  参考文献：
  名称：

  Biocatalytic resolutions of sulfinylalkanoates: a facile route to optically active sulfoxides

  摘要：

  Two methods are presented for kinetic resolutions of compounds containing ester and sulfoxide functionalities (sulfinylalkanoates). In the first a crude lipase preparation from Pseudomonas sp. (K10) mediates enantioselective hydrolysis of these esters in an aqueous environment. The second method uses the same lipase preparation to promote enantioselective transesterifications with alcohols in hexane. Both procedures are suitable for preparation of sulfinylalkanoates where the ester and sulfoxide groups are separated by one or two methylene units (sulfinylacetates and sulfinylpropanoates) but compounds with three methylene "spacer groups" (sulfinylbutanoates) are not substrates for the lipase under either set of conditions.

  DOI：

  10.1021/jo00030a044

文献信息

• Biocatalytic resolutions of sulfinylalkanoates: a facile route to optically active sulfoxides
  作者：Kevin Burgess、Ian Henderson、Kwok Kan Ho

  DOI：10.1021/jo00030a044

  日期：1992.2

  Two methods are presented for kinetic resolutions of compounds containing ester and sulfoxide functionalities (sulfinylalkanoates). In the first a crude lipase preparation from Pseudomonas sp. (K10) mediates enantioselective hydrolysis of these esters in an aqueous environment. The second method uses the same lipase preparation to promote enantioselective transesterifications with alcohols in hexane. Both procedures are suitable for preparation of sulfinylalkanoates where the ester and sulfoxide groups are separated by one or two methylene units (sulfinylacetates and sulfinylpropanoates) but compounds with three methylene "spacer groups" (sulfinylbutanoates) are not substrates for the lipase under either set of conditions.