tert-butyl {3-[2-(6-methyl-2-oxo-7-oxabicyclo[4.1.0]hept-1-yl)ethyl]phenyl}carbamate | 1338951-50-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl {3-[2-(6-methyl-2-oxo-7-oxabicyclo[4.1.0]hept-1-yl)ethyl]phenyl}carbamate
• CAS: 1338951-50-0
• 化学式: C₂₀H₂₇NO₄
• 分子量: 345.439
• InChiKey: LKGKIDNJNLLJDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  67.93
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl {3-[2-(6-methyl-2-oxo-7-oxabicyclo[4.1.0]hept-1-yl)ethyl]phenyl}carbamate 在 氯化锆(IV) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 tert-butyl (8a-hydroxy-4b-methyl-8-oxo-4b,5,6,7,8,8a,9,10-octahydrophenanthren-4-yl)carbamate 、 tert-butyl (8a-hydroxy-4b-methyl-8-oxo-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl)carbamate
  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：

  tert-butyl {3-[2-(2-methyl-6-oxocyclohex-1-en-1-yl)ethyl]phenyl}carbamate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 tert-butyl {3-[2-(6-methyl-2-oxo-7-oxabicyclo[4.1.0]hept-1-yl)ethyl]phenyl}carbamate
  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