di((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) [2-(methylsulfanyl)-3,6-dihydro-2H-thiopyran-2-yl]phosphonate | 1361955-30-7

• 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: di((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) [2-(methylsulfanyl)-3,6-dihydro-2H-thiopyran-2-yl]phosphonate
• 英文别名: 6-[bis[[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy]-oxidophosphaniumyl]-6-methylsulfanyl-2,5-dihydrothiopyran
• CAS: 1361955-30-7
• 化学式: C₂₆H₄₇O₃PS₂
• 分子量: 502.763
• InChiKey: JAECZALYLSDIOQ-HMAMVKBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  92.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3-丁二烯 、 S-methyl O,O-di-(-)-menthyl phosphonodithioformate 以 二氯甲烷 为溶剂， 以79%的产率得到di((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) [2-(methylsulfanyl)-3,6-dihydro-2H-thiopyran-2-yl]phosphonate
  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.