(1S,2R)-2-(2-phenylpropan-2-yl)cyclohexyl 2-(methylthio)-2-thioxoacetate | 1361955-11-4

• 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-(2-phenylpropan-2-yl)cyclohexyl 2-(methylthio)-2-thioxoacetate
• CAS: 1361955-11-4
• 化学式: C₁₈H₂₄O₂S₂
• 分子量: 336.519
• InChiKey: MAZWYPUMGCYOJT-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,2R)-2-(2-phenylpropan-2-yl)cyclohexyl 2-(methylthio)-2-thioxoacetate 、 2,3-二甲基-1,3-丁二烯 在 copper(II) bis(trifluoromethanesulfonate) 、 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 为溶剂， 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
• 作为产物：
  描述：

  (1S,2R)-(+)-反-2-(1-甲基-1-苯乙基)环己醇 在 sulfur 、 N,N-二甲基苯胺 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 18.8h， 生成 (1S,2R)-2-(2-phenylpropan-2-yl)cyclohexyl 2-(methylthio)-2-thioxoacetate
  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