(E)-1-[(4S)-5,5-dimethyl-4-propan-2-yl-2-sulfanylidene-1,3-oxazolidin-3-yl]but-2-en-1-one | 877377-54-3

• 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: (E)-1-[(4S)-5,5-dimethyl-4-propan-2-yl-2-sulfanylidene-1,3-oxazolidin-3-yl]but-2-en-1-one
• CAS: 877377-54-3
• 化学式: C₁₂H₁₉NO₂S
• 分子量: 241.354
• InChiKey: PUZNFMHXUHCMSM-FGEFZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-[(4S)-5,5-dimethyl-4-propan-2-yl-2-sulfanylidene-1,3-oxazolidin-3-yl]but-2-en-1-one 在 niobium pentachloride 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以50%的产率得到(3'R,4S)-3-(1'-oxo-3'-mercaptobutyl)-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
• 作为产物：
  描述：

  (S)-3-氨基-2,4-二甲基戊-2-醇 在 sodium hydride 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 20.0h， 生成 (E)-1-[(4S)-5,5-dimethyl-4-propan-2-yl-2-sulfanylidene-1,3-oxazolidin-3-yl]but-2-en-1-one
  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

• Novel rearrangement of N-enoyl oxazolidinethiones to N-substituted 1,3-thiazine-2,4-diones promoted by NbCl5
  作者：Hector Hernández、Sylvain Bernès、Leticia Quintero、Estibaliz Sansinenea、Aurelio Ortiz

  DOI：10.1016/j.tetlet.2005.12.019

  日期：2006.2

  NbCl5 has been employed as promoter of a novel rearrangement to afford chiral N-substituted 1,3-thiazine-2,4-diones with one or two new stereogenic centers from di- and trisubstituted N-enoyl oxazolidinethiones. The trisubstituted E-isomers provide the anti-diastereomers mainly.

  NbCl 5已被用作新型重排的促进剂，以提供具有一个或两个来自二和三取代的N-烯酰基恶唑烷硫酮的新的立体异构中心的手性N-取代的1,3-噻嗪-2,4-二酮。三取代的E-异构体主要提供抗-非对映异构体。
• (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
  作者：Aurelio Ortiz、Leticia Quintero、Hector Hernández、Sotero Maldonado、Guadalupe Mendoza、Sylvain Bernès

  DOI：10.1016/s0040-4039(02)02837-x

  日期：2003.2

  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.