1-[2-(3-isopropyl-2-methoxyphenyl)ethyl]-6-methyl-7-oxabicyclo[4.1.0]heptan-2-one | 1338951-58-8

• 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: 1-[2-(3-isopropyl-2-methoxyphenyl)ethyl]-6-methyl-7-oxabicyclo[4.1.0]heptan-2-one
• 英文别名: 1-[2-(2-Methoxy-3-propan-2-ylphenyl)ethyl]-6-methyl-7-oxabicyclo[4.1.0]heptan-2-one；1-[2-(2-methoxy-3-propan-2-ylphenyl)ethyl]-6-methyl-7-oxabicyclo[4.1.0]heptan-2-one
• CAS: 1338951-58-8
• 化学式: C₁₉H₂₆O₃
• 分子量: 302.414
• InChiKey: CCOZPKQUFZBZHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[2-(3-isopropyl-2-methoxyphenyl)ethyl]-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90%的产率得到cis-10a-hydroxy-7-isopropyl-8-methoxy-4a-methyl-3,4,4a,9,10,10a-hexahydrophenanthren-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-(3-isopropyl-2-methoxyphenyl)ethyl]-3-methylcyclohex-2-en-1-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以87%的产率得到1-[2-(3-isopropyl-2-methoxyphenyl)ethyl]-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

文献信息

• Cationic cyclization of keto-epoxides mediated by zirconium(IV) tetrachloride: diastereoselective synthesis of cis-decalinols
  作者：Sylvie Goncalves、Marc Nicolas、Philippe Maillos、Rachid Baati

  DOI：10.1016/j.tet.2011.08.050

  日期：2011.10

  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.