Menthyl-S-methyl-xanthogenat | 168398-55-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Menthyl-S-methyl-xanthogenat
• 英文别名: O-[(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexyl] methylsulfanylmethanethioate
• CAS: 168398-55-8
• 化学式: C₁₂H₂₂OS₂
• 分子量: 246.438
• InChiKey: OUQVQJNYRJQTDS-AXFHLTTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  66.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Menthyl-S-methyl-xanthogenat 在 氨 作用下， 以 乙醇 、 水 为溶剂， 生成 O-[(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexyl] carbamothioate
  参考文献：
  名称：

  Asymmetric Three-Component Domino Reaction: An Original Access to Chiral Nonracemic 1,3-Thiazin-2-ones

  摘要：

  A new asymmetric three-component domino process, based on a diastereoselective hetero-Diels-Alder reaction, involving an aldehyde, an alkene, and a chiral thiocarbamate was developed. The chiral auxiliary is directly removed during this process, leading to enantioenriched 2H-1,3-thiazin-2-ones with up to 96% ee.

  DOI：

  10.1021/ol4027446
• 作为产物：
  描述：

  二硫化碳 、 D-薄荷醇 、 碘甲烷 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 Menthyl-S-methyl-xanthogenat
  参考文献：
  名称：

  Asymmetric Three-Component Domino Reaction: An Original Access to Chiral Nonracemic 1,3-Thiazin-2-ones

  摘要：

  A new asymmetric three-component domino process, based on a diastereoselective hetero-Diels-Alder reaction, involving an aldehyde, an alkene, and a chiral thiocarbamate was developed. The chiral auxiliary is directly removed during this process, leading to enantioenriched 2H-1,3-thiazin-2-ones with up to 96% ee.

  DOI：

  10.1021/ol4027446

文献信息

• A synthetic approach to the cis-fused marine pyranopyrans, (3E)- and (3Z)-dactomelyne. X-ray structure of a rare organomercurial
  作者：Alan P. Kozikowski、Jaemoon Lee

  DOI：10.1021/jo00290a014

  日期：1990.2
• Asymmetric Three-Component Domino Reaction: An Original Access to Chiral Nonracemic 1,3-Thiazin-2-ones
  作者：Flavie Peudru、Fabien Le Cavelier、Jean-François Lohier、Mihaela Gulea、Vincent Reboul

  DOI：10.1021/ol4027446

  日期：2013.11.15

  A new asymmetric three-component domino process, based on a diastereoselective hetero-Diels-Alder reaction, involving an aldehyde, an alkene, and a chiral thiocarbamate was developed. The chiral auxiliary is directly removed during this process, leading to enantioenriched 2H-1,3-thiazin-2-ones with up to 96% ee.