(1S,4R,5S)-8-(methoxymethylene)-1-methyl-4-(methylethyl)bicyclo[3.2.1]octan-6-one | 1309660-05-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,4R,5S)-8-(methoxymethylene)-1-methyl-4-(methylethyl)bicyclo[3.2.1]octan-6-one
• 英文别名: (1S,4R,5S)-8-(methoxymethylidene)-1-methyl-4-propan-2-ylbicyclo[3.2.1]octan-6-one
• CAS: 1309660-05-6
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: COXFNKVNLBDKEX-SWHYSGLUSA-N

物化性质

• 沸点：
  304.1±15.0 °C(Predicted)
• 密度：
  1.059±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,4R,5S)-8-(methoxymethylene)-1-methyl-4-(methylethyl)bicyclo[3.2.1]octan-6-one 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.5h， 生成 methyl (1S,2R,5R)-8-(methoxymethylene)-5-methyl-2-(methylethyl)-7-[(trifluoromethyl)sulfonyloxy]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

文献信息

• First total syntheses of bicyclic marine sesquiterpenoids drechslerines A and B
  作者：Hisahiro Hagiwara、Masakazu Fukushima、Kimihiko Kinugawa、Takuya Matsui、Takashi Hoshi、Toshio Suzuki

  DOI：10.1016/j.tet.2011.04.007

  日期：2011.6

  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.