methyl (1R,2R,6S,7R)-8-oxotricyclo[5.4.0.0^2,6]undec-9-ene-1-carboxylate | 491600-91-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1R,2R,6S,7R)-8-oxotricyclo[5.4.0.0^2,6]undec-9-ene-1-carboxylate
• 英文别名: methyl (1R,2R,6S,7R)-8-oxotricyclo[5.4.0.02,6]undec-9-ene-1-carboxylate
• CAS: 491600-91-0
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: PIHMJTRDVMZUNF-IZWKTGJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (1R,2R,6S,7R)-8-oxotricyclo[5.4.0.0^2,6]undec-9-ene-1-carboxylate 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 8.0h， 生成 methyl (1'R,2'R,4R,5R,6'S,7'R)-4,5-dimethylspiro[1,3-dioxolane-2,8'-tricyclo[5.4.0.02,6]undecane]-1'-carboxylate
  参考文献：
  名称：

  [2+2] Photoadditions with chiral 2,5-cyclohexadienone synthons

  摘要：

  Three chiral 2,5-cyclohexadienone synthons bearing different chiral auxiliaries were examined in [2+2] photoadditions with cyclopentene. Regeneration of the 'masked' double bond in the adducts resulted in the preparation of optically active 5-4-6 adducts. The enantiomeric purity of each adduct was found to be >95% using comparative C-13 NMR analysis of the appropriate ketals. The asymmetry induced in the cycloaddition step of our methodology indicated that the facial selectivity was directly correlated to the degree of steric bulk of the chiral auxiliary oil the synthon. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00339-7
• 作为产物：
  描述：

  methyl 4,5-O-ethylpropylidene-3-dehydro-4-epi-shikimate 在 盐酸 、 硫酸 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 32.0h， 生成 methyl (1R,2R,6S,7R)-8-oxotricyclo[5.4.0.0^2,6]undec-9-ene-1-carboxylate
  参考文献：
  名称：

  [2+2] Photoadditions with chiral 2,5-cyclohexadienone synthons

  摘要：

  Three chiral 2,5-cyclohexadienone synthons bearing different chiral auxiliaries were examined in [2+2] photoadditions with cyclopentene. Regeneration of the 'masked' double bond in the adducts resulted in the preparation of optically active 5-4-6 adducts. The enantiomeric purity of each adduct was found to be >95% using comparative C-13 NMR analysis of the appropriate ketals. The asymmetry induced in the cycloaddition step of our methodology indicated that the facial selectivity was directly correlated to the degree of steric bulk of the chiral auxiliary oil the synthon. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00339-7

文献信息

• [2+2] Photoadditions with chiral 2,5-cyclohexadienone synthons
  作者：Gordon L. Lange、Craig C. Humber、Jeffrey M. Manthorpe

  DOI：10.1016/s0957-4166(02)00339-7

  日期：2002.7

  Three chiral 2,5-cyclohexadienone synthons bearing different chiral auxiliaries were examined in [2+2] photoadditions with cyclopentene. Regeneration of the 'masked' double bond in the adducts resulted in the preparation of optically active 5-4-6 adducts. The enantiomeric purity of each adduct was found to be >95% using comparative C-13 NMR analysis of the appropriate ketals. The asymmetry induced in the cycloaddition step of our methodology indicated that the facial selectivity was directly correlated to the degree of steric bulk of the chiral auxiliary oil the synthon. (C) 2002 Elsevier Science Ltd. All rights reserved.