2-(2-(cyclohex-1-en-1-yl)ethyl)-3-methylcyclohex-2-enone | 101100-13-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-(cyclohex-1-en-1-yl)ethyl)-3-methylcyclohex-2-enone
• CAS: 101100-13-4
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: HRAQVSUADUKTIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  在 水 作用下， 以 乙腈 为溶剂， 以1.12 g的产率得到2-(2-(cyclohex-1-en-1-yl)ethyl)-3-methylcyclohex-2-enone
  参考文献：
  名称：

  An efficient one-pot four-step domino reaction for the synthesis of C2-substituted 3-methylcyclohex-2-enones

  摘要：

  An efficient one-pot four-step domino reaction of substituted beta-ketoesters has been optimized giving rise to a large panel of C2-substituted 3-methylcyclohex-2-enones, an important scaffold for the preparation of various initiators for cationic or radical cyclizations. The developed methodology is quite general and applicable to a wide range of beta-ketoester substrates, allowing the introduction of various functionalities at the C2 position of the 3-methylcyclohex-2-enones, in good to excellent yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.029