(2R,3E,5R,7S,10E)-3,6,6,10-tetramethyltricyclo[10.3.0.05,7]pentadeca-1(12),3,10-triene-2,9-diol | 271597-34-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3E,5R,7S,10E)-3,6,6,10-tetramethyltricyclo[10.3.0.05,7]pentadeca-1(12),3,10-triene-2,9-diol
• CAS: 271597-34-3
• 化学式: C₁₉H₂₈O₂
• 分子量: 288.43
• InChiKey: CWLKOMIRFRDESW-IUMBBLSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3E,5R,7S,10E)-3,6,6,10-tetramethyltricyclo[10.3.0.05,7]pentadeca-1(12),3,10-triene-2,9-diol 在 二甲基亚砜 、 2-碘酰基苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以82%的产率得到(3E,5R,7S,10E)-3,6,6,10-tetramethyltricyclo[10.3.0.05,7]pentadeca-1(12),3,10-triene-2,9-dione
  参考文献：
  名称：

  Facile construction of the lathyrane-type framework via Cr–Ni-mediated cyclization as a key step

  摘要：

  A tricyclic compound (1) that has a lathyrane-type framework was designed as a model compound of the key intermediate of some diterpenes from Euphorbiacea and Thymeleacea. Two fragments 2 and 3 were derived from commercially available methyl cyclopentanone-2-carboxylate and (+)-3-carene, respectively. These fragments were coupled by a Cr(II)-Ni(II)-mediated reaction, followed by cyclization under the same conditions to afford 1 in moderate yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00133-7
• 作为产物：
  描述：

  2,2-dimethyl-3-(2-oxopropyl)-cis-cyclopropane-1-acetaldehyde dimethyl acetal 在 chromium dichloride 、 盐酸 、 Schwartz's reagent 、 正丁基锂 、 高氯酸 、 五氯化磷 、 碘 、 三乙基硼氢化锂 、 臭氧 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 32.0h， 生成 (2R,3E,5R,7S,10E)-3,6,6,10-tetramethyltricyclo[10.3.0.05,7]pentadeca-1(12),3,10-triene-2,9-diol
  参考文献：
  名称：

  Facile construction of the lathyrane-type framework via Cr–Ni-mediated cyclization as a key step

  摘要：

  A tricyclic compound (1) that has a lathyrane-type framework was designed as a model compound of the key intermediate of some diterpenes from Euphorbiacea and Thymeleacea. Two fragments 2 and 3 were derived from commercially available methyl cyclopentanone-2-carboxylate and (+)-3-carene, respectively. These fragments were coupled by a Cr(II)-Ni(II)-mediated reaction, followed by cyclization under the same conditions to afford 1 in moderate yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00133-7

文献信息

• Facile construction of the lathyrane-type framework via Cr–Ni-mediated cyclization as a key step
  作者：Tomoo Matsuura、Shosuke Yamamura、Yukimasa Terada

  DOI：10.1016/s0040-4039(00)00133-7

  日期：2000.3

  A tricyclic compound (1) that has a lathyrane-type framework was designed as a model compound of the key intermediate of some diterpenes from Euphorbiacea and Thymeleacea. Two fragments 2 and 3 were derived from commercially available methyl cyclopentanone-2-carboxylate and (+)-3-carene, respectively. These fragments were coupled by a Cr(II)-Ni(II)-mediated reaction, followed by cyclization under the same conditions to afford 1 in moderate yield. (C) 2000 Elsevier Science Ltd. All rights reserved.