4,5-dimethyl-2-(methylsulfanyl)-3,6-dihydro-2H-thiopyran-2-carboxylic acid brucinium salt | 1361955-35-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 马钱子生物碱
• 英文名称: 4,5-dimethyl-2-(methylsulfanyl)-3,6-dihydro-2H-thiopyran-2-carboxylic acid brucinium salt
• CAS: 1361955-35-2
• 化学式: C₉H₁₄O₂S₂*C₂₃H₂₆N₂O₄
• 分子量: 612.811
• InChiKey: DGUSPIAZICQQFC-SFUMKHBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  42.0
• 可旋转键数：
  4.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  88.54
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  2,3-二甲基-1,3-丁二烯 在 copper(II) bis(trifluoromethanesulfonate) 、 potassium hydroxide 、 2,2′-亚甲基双[(4R,5S)-4,5-二苯基-2-噁唑啉] 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 15.0h， 生成 4,5-dimethyl-2-(methylsulfanyl)-3,6-dihydro-2H-thiopyran-2-carboxylic acid brucinium salt
  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