methyl (3aS,6aR)-2-hydroxy-4,4,5-trimethyl-6a-vinyl-3,3a,4,6a-tetrahydropentalene-1-carboxylate | 1146937-23-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基硫酯
• 英文名称: methyl (3aS,6aR)-2-hydroxy-4,4,5-trimethyl-6a-vinyl-3,3a,4,6a-tetrahydropentalene-1-carboxylate
• CAS: 1146937-23-6
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: BQTIAAZDCKMNSS-XHDPSFHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl (3aS,6aR)-2-hydroxy-4,4,5-trimethyl-6a-vinyl-3,3a,4,6a-tetrahydropentalene-1-carboxylate 在 potassium carbonate 作用下， 以 丙酮 、 苯 为溶剂， 反应 2.5h， 生成 methyl (1R,2R,5S)-2-allyl-6,6,7-trimethyl-3-oxo-1-vinylbicyclo[3.3.0]oct-7-ene-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 、 copper(l) iodide 、 rhodium(II) acetate dimer 、 双氧水 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 1.83h， 生成 methyl (3aS,6aR)-2-hydroxy-4,4,5-trimethyl-6a-vinyl-3,3a,4,6a-tetrahydropentalene-1-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。