(3'S,6S)-3'-(4-methylphenyl)spiro[8,9-dihydro-7H-benzo[7]annulene-6,2'-oxirane]-5-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3'S,6S)-3'-(4-methylphenyl)spiro[8,9-dihydro-7H-benzo[7]annulene-6,2'-oxirane]-5-one
• 化学式: C₁₉H₁₈O₂
• 分子量: 278.351
• InChiKey: YGWPGDCQINZONS-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  E-2-(4'-methylbenzylidene)-1-benzosuberone 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 218.0h， 生成 (3'S,6S)-3'-(4-methylphenyl)spiro[8,9-dihydro-7H-benzo[7]annulene-6,2'-oxirane]-5-one
  参考文献：
  名称：

  Stereoselective epoxidation of 2-arylidene-1-indanones and 2-arylidene-1-benzosuberones

  摘要：

  Oxidation of the (E) and (Z) isomers of 2-arylidene-1-indanones (1) and 2-arylidene-1-benzosuberones (4) by alkaline hydrogen peroxide (method i) afforded the spiroepoxides trans-2a-g and trans-5a-g from both isomers as sole products in high yields. On the other hand, dimethyldioxirane epoxidation (method ii) of the (E) isomers 1a-g and 4a-g gave the corresponding trans spiroepoxides in good yields, whereas the (Z) isomers 1a, c, e and 4a, c, e led to the cis spiroepoxides in moderate yields. Dimethyldioxirane oxidation (method ii) of (Z)-1c and (Z)-4c, e gave diones 3c and 6c, e as by-products as well. Epoxidation of(Z)-1a, c, e and (Z)-4a, c, e by m-chloroperoxybenzoic acid (method iii) resulted in ca. 6:1 mixtures of cis-2a, c, e and trans-2a, c, e or cis-5a, c, e and trans-5a, c, e spiroepoxides.

  DOI：

  10.1007/bf00817259

文献信息

• Stereoselective epoxidation of 2-arylidene-1-indanones and 2-arylidene-1-benzosuberones
  作者：W. Adam、J. Hal�sz、Z. J�mbor、A. L�vai、C. Nemes、T. Patonay、G. T�th

  DOI：10.1007/bf00817259

  日期：——

  Oxidation of the (E) and (Z) isomers of 2-arylidene-1-indanones (1) and 2-arylidene-1-benzosuberones (4) by alkaline hydrogen peroxide (method i) afforded the spiroepoxides trans-2a-g and trans-5a-g from both isomers as sole products in high yields. On the other hand, dimethyldioxirane epoxidation (method ii) of the (E) isomers 1a-g and 4a-g gave the corresponding trans spiroepoxides in good yields, whereas the (Z) isomers 1a, c, e and 4a, c, e led to the cis spiroepoxides in moderate yields. Dimethyldioxirane oxidation (method ii) of (Z)-1c and (Z)-4c, e gave diones 3c and 6c, e as by-products as well. Epoxidation of(Z)-1a, c, e and (Z)-4a, c, e by m-chloroperoxybenzoic acid (method iii) resulted in ca. 6:1 mixtures of cis-2a, c, e and trans-2a, c, e or cis-5a, c, e and trans-5a, c, e spiroepoxides.