(1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl 4,5-dimethyl-2-(methylsulfanyl)-3,6-dihydro-2H-thiopyran-2-carboxylate | 1361955-23-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl 4,5-dimethyl-2-(methylsulfanyl)-3,6-dihydro-2H-thiopyran-2-carboxylate
• 英文别名: [(1S,2R)-2-(2-phenylpropan-2-yl)cyclohexyl] (6S)-3,4-dimethyl-6-methylsulfanyl-2,5-dihydrothiopyran-6-carboxylate
• CAS: 1361955-23-8
• 化学式: C₂₄H₃₄O₂S₂
• 分子量: 418.665
• InChiKey: XGITWNPXHQMDGZ-HFMPRLQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (1S,2R)-(+)-反-2-(1-甲基-1-苯乙基)环己醇 在 copper(II) bis(trifluoromethanesulfonate) 、 sulfur 、 N,N-二甲基苯胺 、 三乙胺 、 2,2′-亚甲基双[(4R,5S)-4,5-二苯基-2-噁唑啉] 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 18.8h， 生成 (1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl 4,5-dimethyl-2-(methylsulfanyl)-3,6-dihydro-2H-thiopyran-2-carboxylate 、 (1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl 4,5-dimethyl-2-(methylsulfanyl)-3,6-dihydro-2H-thiopyran-2-carboxylate
  参考文献：
  名称：

  Asymmetric diastereoselective thia-hetero-Diels–Alder reactions of dithioesters

  摘要：

  Asymmetric thia-Diels-Alder reactions involving new dithioesters bearing a chiral auxiliary are described, with diastereoselectivities up to 78%. Double-stereodifferentiating experiments employing chiral substrates in the presence of a chiral Lewis acid catalyst have been also carried out and, in this case, a diastereomeric excess of 90% was reached. The absolute stereochemistry of cycloadducts resulting from dithiooxalates and carbonyloxazolidinone dithioesters was assigned based on an X-ray structure and chemical correlation. In order to rationalize the sense of the chiral induction, stereochemical models for Cu(II)/bis(oxazoline)/dithioester complexes are proposed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.039

文献信息

• Asymmetric diastereoselective thia-hetero-Diels–Alder reactions of dithioesters
  作者：Hélène Dentel、Isabelle Chataigner、Jean-François Lohier、Mihaela Gulea

  DOI：10.1016/j.tet.2012.01.039

  日期：2012.3

  Asymmetric thia-Diels-Alder reactions involving new dithioesters bearing a chiral auxiliary are described, with diastereoselectivities up to 78%. Double-stereodifferentiating experiments employing chiral substrates in the presence of a chiral Lewis acid catalyst have been also carried out and, in this case, a diastereomeric excess of 90% was reached. The absolute stereochemistry of cycloadducts resulting from dithiooxalates and carbonyloxazolidinone dithioesters was assigned based on an X-ray structure and chemical correlation. In order to rationalize the sense of the chiral induction, stereochemical models for Cu(II)/bis(oxazoline)/dithioester complexes are proposed. (C) 2012 Elsevier Ltd. All rights reserved.