methyl 2-(methylthio)-3-hydroxy-3-phenylpropionate | 41769-17-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl 2-(methylthio)-3-hydroxy-3-phenylpropionate
• 英文别名: methyl 3-hydroxy-2-methylsulfanyl-3-phenylpropanoate
• CAS: 41769-17-9
• 化学式: C₁₁H₁₄O₃S
• 分子量: 226.296
• InChiKey: NKRXQGDQYYMKGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(methylthio)-3-hydroxy-3-phenylpropionate 、 2,2-二甲氧基丙烷 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 生成 acetonide of 2-(methylthio)-3-phenylpropane-1,3-diol 、 acetonide of 2-(methylthio)-3-phenylpropane-1,3-diol
  参考文献：
  名称：

  Design of .alpha.-alkyl-.beta.-hydroxy esters suitable for providing optical resolution by lipase hydrolysis

  摘要：

  A study of the lipase-catalyzed hydrolyses of various alpha-substituted beta-acetoxy esters revealed that a sulfur functional group in the ester, which could play an important role in the stereorecognition by lipase A6 (Aspergillus sp.) and an anti conformation in the ester, promotes satisfactory results in the hydrolysis.

  DOI：

  10.1021/jo00002a054
• 作为产物：
  描述：

  甲基硫代乙酸甲酯 、 苯甲醛 在 lithium diisopropyl amide 作用下， 生成 methyl 2-(methylthio)-3-hydroxy-3-phenylpropionate
  参考文献：
  名称：

  Design of .alpha.-alkyl-.beta.-hydroxy esters suitable for providing optical resolution by lipase hydrolysis

  摘要：

  A study of the lipase-catalyzed hydrolyses of various alpha-substituted beta-acetoxy esters revealed that a sulfur functional group in the ester, which could play an important role in the stereorecognition by lipase A6 (Aspergillus sp.) and an anti conformation in the ester, promotes satisfactory results in the hydrolysis.

  DOI：

  10.1021/jo00002a054

文献信息

• Ligand-Promoted, Boron-Mediated Chemoselective Carboxylic Acid Aldol Reaction
  作者：Hideoki Nagai、Yuya Morita、Yohei Shimizu、Motomu Kanai

  DOI：10.1021/acs.orglett.6b00914

  日期：2016.5.6

  selective aldol reaction mediated by boron compounds and a mild organic base (DBU) was developed. Inclusion of electron-withdrawing groups in the amino acid derivative ligands reacted with BH3·SMe2 forms a boron promoter with increased Lewis acidity at the boron atom and facilitated the carboxylic acid selective enolate formation, even in the presence of other carbonyl groups such as amides, esters, ketones

  开发了由硼化合物和温和的有机碱（DBU）介导的第一个羧酸选择性羟醛反应。与BH 3 ·SMe 2反应的氨基酸衍生物配体中包含吸电子基团，形成硼促进剂，在硼原子上路易斯酸度增加，即使在存在其他羰基如酰胺，酯，酮或脂族醛。出色的配体效应导致了包括生物相关化合物在内的广泛底物范围。
• ITOH, TOSHIYUKI;KURODA, KEIKO;TOMOSADA, MIKI;TAKAGI, YUMIKO, J. ORG. CHEM., 56,(1991) N, C. 797-804
  作者：ITOH, TOSHIYUKI、KURODA, KEIKO、TOMOSADA, MIKI、TAKAGI, YUMIKO

  DOI：——

  日期：——
• Design of .alpha.-alkyl-.beta.-hydroxy esters suitable for providing optical resolution by lipase hydrolysis
  作者：Toshiyuki Itoh、Keiko Kuroda、Miki Tomosada、Yumiko Takagi

  DOI：10.1021/jo00002a054

  日期：1991.1

  A study of the lipase-catalyzed hydrolyses of various alpha-substituted beta-acetoxy esters revealed that a sulfur functional group in the ester, which could play an important role in the stereorecognition by lipase A6 (Aspergillus sp.) and an anti conformation in the ester, promotes satisfactory results in the hydrolysis.