(2'S,3'R,4S)-3-(1'-oxo-2'-methyl-3'-mercaptobutyl)-4-isopropyl-5,5-dimethyl-1,3-oxazolidinone | 850733-68-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (2'S,3'R,4S)-3-(1'-oxo-2'-methyl-3'-mercaptobutyl)-4-isopropyl-5,5-dimethyl-1,3-oxazolidinone
• 英文别名: (4S)-5,5-dimethyl-3-[(2S,3R)-2-methyl-3-sulfanylbutanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 850733-68-5
• 化学式: C₁₃H₂₃NO₃S
• 分子量: 273.397
• InChiKey: SOSZJDJFZNVGEM-BBBLOLIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  46.61
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2'S,3'R,4S)-3-(1'-oxo-2'-methyl-3'-mercaptobutyl)-4-isopropyl-5,5-dimethyl-1,3-oxazolidinone 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (2S,3R)-2-Methyl-3-methylsulfanyl-butan-1-ol
  参考文献：
  名称：

  Asymmetric synthesis of 3-methylthio alcohols by intramolecular Michael addition reactions

  摘要：

  Chiral 3-methylthio alcohols have been synthesized through a known intramolecular sulfur transfer reaction that has been carried out in di- and trisubstituted alpha,beta-unsaturated N-enoyl oxazolidinethiones as substrates, giving rise to synlanti-diastereomers. The anti-diastereomer is favored and obtained via a highly diastereo-selective protonation step (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.021
• 作为产物：
  描述：

  (E)-1-((S)-4-Isopropyl-5,5-dimethyl-2-thioxo-oxazolidin-3-yl)-2-methyl-but-2-en-1-one 在 四氯化锡 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 14.0h， 以40%的产率得到(2'S,3'R,4S)-3-(1'-oxo-2'-methyl-3'-mercaptobutyl)-4-isopropyl-5,5-dimethyl-1,3-oxazolidinone
  参考文献：
  名称：

  Asymmetric synthesis of 3-methylthio alcohols by intramolecular Michael addition reactions

  摘要：

  Chiral 3-methylthio alcohols have been synthesized through a known intramolecular sulfur transfer reaction that has been carried out in di- and trisubstituted alpha,beta-unsaturated N-enoyl oxazolidinethiones as substrates, giving rise to synlanti-diastereomers. The anti-diastereomer is favored and obtained via a highly diastereo-selective protonation step (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.021

文献信息

• Chiral Thiols:  The Assignment of Their Absolute Configuration by ¹H NMR
  作者：Silvia Porto、José Manuel Seco、Aurelio Ortiz、Emilio Quiñoá、Ricardo Riguera

  DOI：10.1021/ol7022196

  日期：2007.11.1

  A general NMR spectroscopy protocol for determination of absolute configuration of thiols, that includes the introduction of new aryl-tert-butoxyacetic acids as chiral derivatizing agents (CDAs), is described.

  描述了用于确定硫醇的绝对构型的通用NMR光谱协议，包括引入新的芳基-叔丁氧基乙酸作为手性衍生剂（CDA）。