1-(2-cyclohex-1-en-1-ylethyl)-6-methyl-7-oxabicyclo[4.1.0]heptan-2-one | 1338951-55-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-cyclohex-1-en-1-ylethyl)-6-methyl-7-oxabicyclo[4.1.0]heptan-2-one
• CAS: 1338951-55-5
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: ARRMODBIPOMTOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  29.6
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(2-cyclohex-1-en-1-ylethyl)-6-methyl-7-oxabicyclo[4.1.0]heptan-2-one 在 氯化锆(IV) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以66%的产率得到cis-8a-chloro-10a-hydroxy-4a-methyldodecahydrophenanthren-1(2H)-one
  参考文献：
  名称：

  Cationic cyclization of keto-epoxides mediated by zirconium(IV) tetrachloride: diastereoselective synthesis of cis-decalinols

  摘要：

  10-Methyl-cis-9-decalinols are important motifs in several natural products and key intermediates in total synthesis. Herein, we wish to describe a highly chemo- and diastereoselective cyclization of ketoepoxides leading to 10-methyl-cis-9-decalinols. This method based on the use of zirconium(IV) tetrachloride permits the access to a wide variety of cis-decalinols in good to excellent yields. The cationic cyclization could also be performed with chiral keto-epoxide with complete control of the diastereoselectivity affording cis-bicyclic tertiary alcohol with good enantiomeric excess. The chemo- and the diastereoselectivity are assumed to result from the ability of Zr(IV) to generate highly stable bidentic complexes with alpha-hydroxy-ketone intermediates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.050
• 作为产物：
  描述：

  2-(2-(cyclohex-1-en-1-yl)ethyl)-3-methylcyclohex-2-enone 在 双氧水 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 1-(2-cyclohex-1-en-1-ylethyl)-6-methyl-7-oxabicyclo[4.1.0]heptan-2-one
  参考文献：
  名称：

  Cationic cyclization of keto-epoxides mediated by zirconium(IV) tetrachloride: diastereoselective synthesis of cis-decalinols

  摘要：

  10-Methyl-cis-9-decalinols are important motifs in several natural products and key intermediates in total synthesis. Herein, we wish to describe a highly chemo- and diastereoselective cyclization of ketoepoxides leading to 10-methyl-cis-9-decalinols. This method based on the use of zirconium(IV) tetrachloride permits the access to a wide variety of cis-decalinols in good to excellent yields. The cationic cyclization could also be performed with chiral keto-epoxide with complete control of the diastereoselectivity affording cis-bicyclic tertiary alcohol with good enantiomeric excess. The chemo- and the diastereoselectivity are assumed to result from the ability of Zr(IV) to generate highly stable bidentic complexes with alpha-hydroxy-ketone intermediates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.050