methyl (1R,2R,5R)-8-(methoxymethylene)-5-methyl-2-(methylethyl)bicyclo[3.2.1]oct-6-ene-6-carboxylate | 1312339-61-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (1R,2R,5R)-8-(methoxymethylene)-5-methyl-2-(methylethyl)bicyclo[3.2.1]oct-6-ene-6-carboxylate
• 英文别名: methyl (1R,2R,5R)-8-(methoxymethylidene)-5-methyl-2-propan-2-ylbicyclo[3.2.1]oct-6-ene-6-carboxylate
• CAS: 1312339-61-9
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: NEZWDWZUZINDCS-WQGACYEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (1R,2R,5R)-8-(methoxymethylene)-5-methyl-2-(methylethyl)bicyclo[3.2.1]oct-6-ene-6-carboxylate 在 高氯酸 、 二异丁基氢化铝 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 [(1R,4R,5R,8S)-7-(hydroxymethyl)-1-methyl-4-(methylethyl)bicyclo[3.2.1]oct-6-en-8-yl]methan-1-ol
  参考文献：
  名称：

  First total syntheses of bicyclic marine sesquiterpenoids drechslerines A and B

  摘要：

  The first total syntheses of the bicyclic sesquiterpenoids drechslerines A (1) and B (2), which were isolated from the algicolous fungus Drechslera dematioidea in the marine red alga Liagora viscida, has been accomplished starting from (S)-carvone (13) via three palladium-catalyzed reactions, namely, diastereoselective allylation, conjugate reduction, and carbon monoxide insertion, as the key reactions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.007
• 作为产物：
  描述：

  methyl (1S,2R,5R)-8-(methoxymethylene)-5-methyl-2-(methylethyl)-7-[(trifluoromethyl)sulfonyloxy]bicyclo[3.2.1]oct-6-ene-6-carboxylate 在 甲酸 、 三正丁胺 、 palladium diacetate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以96%的产率得到methyl (1R,2R,5R)-8-(methoxymethylene)-5-methyl-2-(methylethyl)bicyclo[3.2.1]oct-6-ene-6-carboxylate
  参考文献：
  名称：

  First total syntheses of bicyclic marine sesquiterpenoids drechslerines A and B

  摘要：

  The first total syntheses of the bicyclic sesquiterpenoids drechslerines A (1) and B (2), which were isolated from the algicolous fungus Drechslera dematioidea in the marine red alga Liagora viscida, has been accomplished starting from (S)-carvone (13) via three palladium-catalyzed reactions, namely, diastereoselective allylation, conjugate reduction, and carbon monoxide insertion, as the key reactions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.007