methyl (5S)-6,6,7-trimethyl-3-oxobicyclo[3.3.0]octa-1,7-diene-2-carboxylate | 1146937-19-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (5S)-6,6,7-trimethyl-3-oxobicyclo[3.3.0]octa-1,7-diene-2-carboxylate
• CAS: 1146937-19-0
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: NJUVRDRXJGWCFM-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl (5S)-6,6,7-trimethyl-3-oxobicyclo[3.3.0]octa-1,7-diene-2-carboxylate 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以86%的产率得到methyl (3S,5S)-3-hydroxy-6,6,7-trimethylbicyclo[3.3.0]octa-1,7-diene-2-carboxylate
  参考文献：
  名称：

  Enantiospecific synthesis of angular triquinanes

  摘要：

  The enantiospecific synthesis of angular triquinanes has been developed starting from the readily available (S)-campholenaldehyde. Two alternate strategies have been used, one employing a Johnson's orthoester Claisen rearrangement followed by an intramolecular cyclopropanation and regioselective cyclopropane ring cleavage, and a second one based on a RCM reaction. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.08.016
• 作为产物：
  描述：

  methyl 2-diazo-3-oxo-4-[(1S)-2,2,3-trimethylcyclopent-3-en-1-yl]butanoate 在 吡啶 、 rhodium(II) acetate dimer 、 双氧水 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 methyl (5S)-6,6,7-trimethyl-3-oxobicyclo[3.3.0]octa-1,7-diene-2-carboxylate
  参考文献：
  名称：

  Enantiospecific synthesis of angular triquinanes

  摘要：

  The enantiospecific synthesis of angular triquinanes has been developed starting from the readily available (S)-campholenaldehyde. Two alternate strategies have been used, one employing a Johnson's orthoester Claisen rearrangement followed by an intramolecular cyclopropanation and regioselective cyclopropane ring cleavage, and a second one based on a RCM reaction. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.08.016

文献信息

• Enantiospecific approach to the tricyclic core structure of tricycloillicinone, ialibinones, and takaneones via ring-closing metathesis reaction
  作者：A. Srikrishna、B. Beeraiah、V. Gowri

  DOI：10.1016/j.tet.2009.01.096

  日期：2009.3

  Enantiospecific synthesis of the tricyclic core structure present in the biologically active natural products tricycloillicinone, ialibinones, and takaneones, starting from the readily available campholenaldehyde employing a transannular RCM reaction as the key step, has been accomplished.

  从具有环戊二烯基RCM反应作为关键步骤的容易获得的樟脑醛开始，已经完成了对生物活性天然产物三环硅环酮，艾利比诺酮和高铁酮中存在的三环核心结构的对映体特异性合成。