ethyl (1S,2R,5R,7S)-1,7,9,10-tetramethyl-3-oxotricyclo[5.3.0.02,5]dec-9-ene-4-carboxylate | 1370360-58-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ethyl (1S,2R,5R,7S)-1,7,9,10-tetramethyl-3-oxotricyclo[5.3.0.02,5]dec-9-ene-4-carboxylate
• CAS: 1370360-58-9
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: OWVNLWKEGJWODX-NVVPXADQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  [(1S,3S)-3-isopropenyl-1-methyl-2-methylenecyclopentyl]acetic acid 在 dirhodium tetraacetate 、 对甲苯磺酰叠氮 、 草酰氯 、 氨 、 lithium 、 铜 、 碳酸氢钠 、 对甲苯磺酸 、 臭氧 、 copper(II) sulfate 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 环己烷 、 乙腈 、 苯 为溶剂， 反应 33.74h， 生成 ethyl (1S,2R,5R,7S)-1,7,9,10-tetramethyl-3-oxotricyclo[5.3.0.02,5]dec-9-ene-4-carboxylate 、 ethyl (1S,5R,8S)-8,10,11-trimethyl-4-oxotricyclo[6.3.0.01,5]undec-10-ene-3-carboxylate
  参考文献：
  名称：

  The substrate dependent competitive formation of cyclobutanones and cyclopentanones in an intramolecular rhodium carbenoid CH insertion reaction: enantiospecific total synthesis of silphiperfol-6-ene

  摘要：

  The enantiospecific total synthesis of silphiperfol-6-ene has been accomplished starting from the readily available monoterpene (R)-limonene, employing a rhodium carbenoid insertion into the CH bond of a tertiary methyl group. A substrate dependent competitive insertion of the rhodium carbenoid in the gamma- and beta-CH bonds to form cyclopentanone and cyclobutanones, respectively, has been described. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.01.016

文献信息

• The substrate dependent competitive formation of cyclobutanones and cyclopentanones in an intramolecular rhodium carbenoid CH insertion reaction: enantiospecific total synthesis of silphiperfol-6-ene
  作者：Adusumilli Srikrishna、Gopalasetty Nagaraju

  DOI：10.1016/j.tetasy.2012.01.016

  日期：2012.1

  The enantiospecific total synthesis of silphiperfol-6-ene has been accomplished starting from the readily available monoterpene (R)-limonene, employing a rhodium carbenoid insertion into the CH bond of a tertiary methyl group. A substrate dependent competitive insertion of the rhodium carbenoid in the gamma- and beta-CH bonds to form cyclopentanone and cyclobutanones, respectively, has been described. (C) 2012 Elsevier Ltd. All rights reserved.