(4S)-4-异丙基-5,5-二甲基-1,3-恶唑烷-2-硫酮 | 597558-53-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: (4S)-4-异丙基-5,5-二甲基-1,3-恶唑烷-2-硫酮
• 英文名称: (S)-4-isopropyl-5,5-dimethyl-1,3-oxazolidine-2-thione
• 英文别名: (S)-4-isopropyl-5,5-dimethyl-1,3-oxazolidinethione；(S)-4-isopropyl-5,5-dimethyloxazolidine-2-thione；(4S)-5,5-dimethyl-4-propan-2-yl-1,3-oxazolidine-2-thione
• CAS: 597558-53-7
• 化学式: C₈H₁₅NOS
• 分子量: 173.279
• InChiKey: JACWLYWDRFCVBC-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S)-4-异丙基-5,5-二甲基-1,3-恶唑烷-2-硫酮 在 niobium pentachloride sodium hydride 、 samarium(III) trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 (4S)-4-异丙基-5,5-二甲基-1,3-恶唑烷-2-酮
  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：

  N-trifluoroacetyl-(S)-valine methyl ester 在 sodium carbonate 作用下， 以 乙醚 、 水 为溶剂， 反应 32.0h， 生成 (4S)-4-异丙基-5,5-二甲基-1,3-恶唑烷-2-硫酮
  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

• Rearrangement of oxazolidinethiones to thiazolidinediones or thiazinanediones and their application for the synthesis of chiral allylic ureas and α-methyl-β-amino acids
  作者：Rocio Sabala、Jacqueline Hernández、Vladimir Carranza、Rosa L. Meza-León、Sylvain Bernès、Estibaliz Sansinenea、Aurelio Ortiz

  DOI：10.1016/j.tet.2009.11.035

  日期：2010.1

  A novel rearrangement has been found between oxazolidinethiones and acyl halides under N-acylation reaction conditions to afford N-substituted 2,4-thiazolidinediones and N-substituted 1,3-thiazinane-2,4-diones. These heterocycles were used for the synthesis of chiral allylic ureas and α-methyl-β-amino acids.

  在N-酰化反应条件下，在恶唑烷硫酮和酰基卤之间发现了新的重排，以提供N-取代的2,4-噻唑烷二酮和N-取代的1,3-噻嗪烷-2,4-二酮。这些杂环用于合成手性烯丙基脲和α-甲基-β-氨基酸。
• A novel nucleophilic attack to N-enoyl oxazolidinethiones
  作者：Aurelio Ortiz、Leticia Quintero、Guadalupe Mendoza、Sylvain Bernès

  DOI：10.1016/s0040-4039(03)01189-4

  日期：2003.6

  The oxazolidinethione synthon can act as a chiral auxiliary and nucleophile (S−) carrier molecule simultaneously. Surprisingly, the thiolate attacks N-enoyl oxazolidinethiones producing a new heterocycle, as established by X-ray analysis.

  所述oxazolidinethione合成子可作为手性助剂和亲核体（S作用-载体分子同时）。出乎意料的是，如通过X射线分析所确定的，硫醇盐攻击N-烯酰基恶唑烷硫酮，产生新的杂环。
• Synthesis of N-substituted 2,4-thiazolidinediones from oxazolidinethiones
  作者：Guadalupe Mendoza、Hector Hernández、Leticia Quintero、Martha Sosa-Rivadeneyra、Sylvain Bernès、Estibaliz Sansinenea、Aurelio Ortiz

  DOI：10.1016/j.tetlet.2005.09.116

  日期：2005.11

  A novel reaction has been found between oxazolidinethione and bromoacetyl bromide to afford N-substituted 2,4-thiazolidinediones through an intramolecular nucleophilic substitution reaction. Interestingly a step of elimination was carried out in trisubstituted oxazolidinethiones forming a double bond. (c) 2005 Elsevier Ltd. All rights reserved.
• Rearrangement of 5-phenylthiazolidine-2,4-diones to chiral α-ketoamides via α-elimination
  作者：Laura Munive、Sylvain Bernès、Estibaliz Sansinenea、Aurelio Ortiz

  DOI：10.1016/j.tetlet.2010.09.046

  日期：2010.11
• (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.