(3R,8aS)-2,2,8a-trimethyl-3-phenyl-3,6,7,8-tetrahydro-[1,3]oxazolo[3,2-a]pyridine-5-thione | 226545-90-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3R,8aS)-2,2,8a-trimethyl-3-phenyl-3,6,7,8-tetrahydro-[1,3]oxazolo[3,2-a]pyridine-5-thione
• CAS: 226545-90-0
• 化学式: C₁₆H₂₁NOS
• 分子量: 275.415
• InChiKey: JOPKCPIUUYHXTR-ZBFHGGJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  44.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,8aS)-2,2,8a-trimethyl-3-phenyl-3,6,7,8-tetrahydro-[1,3]oxazolo[3,2-a]pyridine-5-thione 在 platinum on activated charcoal ammonium acetate 、 氢气 、 sodium carbonate 作用下， 以 乙醇 、 氯仿 、 溶剂黄146 、 乙酸乙酯 为溶剂， -78.0~75.0 ℃ 、413.68 kPa 条件下， 生成 euphococcinine
  参考文献：
  名称：

  An efficient, asymmetric synthesis of (+)-euphococcinine

  摘要：

  The enantioselective synthesis of (+)-euphococcinine (1), a homotropane alkaloid, has been achieved in five steps from bicyclic lactam 5. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00665-1
• 作为产物：
  描述：

  (3R,8aS)-2,2,8a-trimethyl-3-phenyl-3,6,7,8-tetrahydro-[1,3]oxazolo[3,2-a]pyridin-5-one 在 2,4-双(4-苯氧苯基)-1,3-二硫杂-2,4-二磷杂环丁烷-2,4-二硫化物 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以87%的产率得到(3R,8aS)-2,2,8a-trimethyl-3-phenyl-3,6,7,8-tetrahydro-[1,3]oxazolo[3,2-a]pyridine-5-thione
  参考文献：
  名称：

  An Asymmetric Route to Novel Chiral Cyclohexenones with Spiro-Connected Cyclopentenes. Further Utility of Chiral Bicyclic Thiolactams and the [3,3] Thio-Claisen Products

  摘要：

  Sequential allylation of chiral, nonracemic thiolactam 8 affords clean thio-Claisen [3,3] products ii. The stereoselectivity of the rearrangement was found to be on the order of 10-11:1, with the exo-endo products responsible for the mixture. Addition of hydride or methyllithium-cerium chloride gave clean addition to the thiolactam in the form of its iminium salts 12. Hydrolysis gave 4,4-dialkylcyclohexenones 16, which were cyclized to the cyclopentene derivatives 16 using Grubbs' catalyst.

  DOI：

  10.1021/jo982426q

文献信息

• An Asymmetric Route to Novel Chiral Cyclohexenones with Spiro-Connected Cyclopentenes. Further Utility of Chiral Bicyclic Thiolactams and the [3,3] Thio-Claisen Products
  作者：René M. Lemieux、Paul N. Devine、Mark F. Mechelke、A. I. Meyers

  DOI：10.1021/jo982426q

  日期：1999.5.1

  Sequential allylation of chiral, nonracemic thiolactam 8 affords clean thio-Claisen [3,3] products ii. The stereoselectivity of the rearrangement was found to be on the order of 10-11:1, with the exo-endo products responsible for the mixture. Addition of hydride or methyllithium-cerium chloride gave clean addition to the thiolactam in the form of its iminium salts 12. Hydrolysis gave 4,4-dialkylcyclohexenones 16, which were cyclized to the cyclopentene derivatives 16 using Grubbs' catalyst.
• An efficient, asymmetric synthesis of (+)-euphococcinine
  作者：Mark F Mechelke、A.I Meyers

  DOI：10.1016/s0040-4039(00)00665-1

  日期：2000.6

  The enantioselective synthesis of (+)-euphococcinine (1), a homotropane alkaloid, has been achieved in five steps from bicyclic lactam 5. (C) 2000 Elsevier Science Ltd. All rights reserved.