(3'R,4S)-3-(1'-oxo-3'-mercapto-3'-phenylpropyl)-4-isopropyl-5,5-dimethyl-1,3-oxazolidinone | 850733-77-6

• 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: (3'R,4S)-3-(1'-oxo-3'-mercapto-3'-phenylpropyl)-4-isopropyl-5,5-dimethyl-1,3-oxazolidinone
• 英文别名: (4S)-5,5-dimethyl-3-[(3S)-3-phenyl-3-sulfanylpropanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 850733-77-6
• 化学式: C₁₇H₂₃NO₃S
• 分子量: 321.441
• InChiKey: CSFMPEOGSMGNKY-ZFWWWQNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3'R,4S)-3-(1'-oxo-3'-mercapto-3'-phenylpropyl)-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 (S)-3-Methylsulfanyl-3-phenyl-propan-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：

  N-trifluoroacetyl-(S)-valine methyl ester 在 niobium pentachloride sodium hydride 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 44.0h， 生成 (3'R,4S)-3-(1'-oxo-3'-mercapto-3'-phenylpropyl)-4-isopropyl-5,5-dimethyl-1,3-oxazolidinone
  参考文献：
  名称：

  (S)-4-Isopropyl-5,5-dimethyl-1,3-oxazolidinethione as chiral auxiliary for the intramolecular sulfur transfer in α,β-unsaturated N-acylimides, promoted by NbCl5

  摘要：

  The 1,3-oxazolidinethi one 4 has been synthesized from (S)-valine and used in the intramolecular sulfur transfer in its N-enoyl derivatives in the presence of NbCl5 as catalyst, which, moreover, works as an indicator of the course of the reaction. The adducts have subsequently been transformed into the corresponding beta-mercapto esters by action of Sm(OTf)(3) in methanol. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02837-x

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）。