(4R)-4-allyl-4-((3S)-but-1-en-3-yl)cyclohex-2-enone | 226545-94-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R)-4-allyl-4-((3S)-but-1-en-3-yl)cyclohex-2-enone
• 英文别名: (4R)-4-[(2S)-but-3-en-2-yl]-4-prop-2-enylcyclohex-2-en-1-one
• CAS: 226545-94-4
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: AMNXYDJWTWOYEN-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4R)-4-allyl-4-((3S)-but-1-en-3-yl)cyclohex-2-enone 在 Grubbs catalyst first generation 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以94%的产率得到(1S,5R)-1-methyl-8-oxospiro[4.5]deca-2,6-diene
  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 (4R)-4-allyl-4-((3S)-but-1-en-3-yl)cyclohex-2-enone
  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.