(1S,4R,5R)-1-methyl-4-(methylethyl)bicyclo[3.2.1]octane-6,8-dione | 1309660-03-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,4R,5R)-1-methyl-4-(methylethyl)bicyclo[3.2.1]octane-6,8-dione
• 英文别名: (1S,4R,5R)-1-methyl-4-propan-2-ylbicyclo[3.2.1]octane-6,8-dione
• CAS: 1309660-03-4
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: BFSLCPLCOBANDJ-UISBYWKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三异丙基氯硅烷 、 (1S,4R,5R)-1-methyl-4-(methylethyl)bicyclo[3.2.1]octane-6,8-dione 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以98%的产率得到(1S,4R,5R)-6-[1,1-bis(methylethyl)-2-methyl-1-silapropoxy]-1-methyl-4-(methylethyl)bicyclo[3.2.1]oct-6-en-8-one
  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：

  (1S,4R,5R,6S)-6-hydroxy-4-isopropyl-1-methylbicyclo[3.2.1]octan-8-one 在 Jones reagent 作用下， 以 丙酮 为溶剂， 反应 0.25h， 以95%的产率得到(1S,4R,5R)-1-methyl-4-(methylethyl)bicyclo[3.2.1]octane-6,8-dione
  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.