(3R,8aS)-5-[(E)-but-2-enyl]sulfanyl-2,2,8a-trimethyl-3-phenyl-6-prop-2-enyl-7,8-dihydro-3H-[1,3]oxazolo[3,2-a]pyridine | 1026007-83-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (3R,8aS)-5-[(E)-but-2-enyl]sulfanyl-2,2,8a-trimethyl-3-phenyl-6-prop-2-enyl-7,8-dihydro-3H-[1,3]oxazolo[3,2-a]pyridine
• CAS: 1026007-83-9
• 化学式: C₂₃H₃₁NOS
• 分子量: 369.571
• InChiKey: ROPMKLBWDWBGGW-IPXVJXLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  37.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,8aS)-5-[(E)-but-2-enyl]sulfanyl-2,2,8a-trimethyl-3-phenyl-6-prop-2-enyl-7,8-dihydro-3H-[1,3]oxazolo[3,2-a]pyridine 在 cerium(III) chloride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 (3R,8aS)-6-Allyl-5-ethylsulfanyl-2,2,5,8a-tetramethyl-6-(1-methyl-allyl)-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine
  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
• 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]pyridine-5-thione 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 (3R,8aS)-5-[(E)-but-2-enyl]sulfanyl-2,2,8a-trimethyl-3-phenyl-6-prop-2-enyl-7,8-dihydro-3H-[1,3]oxazolo[3,2-a]pyridine
  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