(5S,6S)-5-acetyl-5-allyl-6-methyloct-7-en-2-one | 226545-96-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5S,6S)-5-acetyl-5-allyl-6-methyloct-7-en-2-one
• 英文别名: (3S)-3-[(2S)-but-3-en-2-yl]-3-prop-2-enylheptane-2,6-dione
• CAS: 226545-96-6
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: HLDGWNHRULCZPN-SMDDNHRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5S,6S)-5-acetyl-5-allyl-6-methyloct-7-en-2-one 在 Grubbs catalyst first generation 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以81%的产率得到4-((1S,2S)-1-Acetyl-2-methyl-cyclopent-3-enyl)-butan-2-one
  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 cerium(III) chloride 、 四丁基磷酸氢铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 26.0h， 生成 (5S,6S)-5-acetyl-5-allyl-6-methyloct-7-en-2-one
  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.