(3R,4aR,5R,6S)-4,4a,5,6-tetrahydro-6-hydroxy-4a,5-dimethyl-3-tetrahydropyranyloxy-2(3H)-naphthalenone | 241813-87-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4aR,5R,6S)-4,4a,5,6-tetrahydro-6-hydroxy-4a,5-dimethyl-3-tetrahydropyranyloxy-2(3H)-naphthalenone
• 英文别名: (3R,4aR,5R,6S)-6-hydroxy-4a,5-dimethyl-3-(oxan-2-yloxy)-3,4,5,6-tetrahydronaphthalen-2-one
• CAS: 241813-87-6
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: JLJDBSFQZUIWLX-FBHOWBOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4aR,5R,6S)-4,4a,5,6-tetrahydro-6-hydroxy-4a,5-dimethyl-3-tetrahydropyranyloxy-2(3H)-naphthalenone 在 4-二甲氨基吡啶 、 2,4,6-三氯苯甲酰氯 、 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 dendryphiellin C
  参考文献：
  名称：

  Synthesis of dendryphiellin C, a trinor-sesquiterpene from a marine source

  摘要：

  Enantioselective synthesis of dendryphiellin C, isolated from cultures of Dendryphiella sarina, has been achieved in a convergent way such as coupling of a C9-branched carboxylic acid 10 with a trinor-eremophilane alcohol 11. The latter was synthesized starting from a chiral building block, (1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 16, which was originally prepared in this group using biochemical transformation as a key step. The synthesis was completed through 12 steps from 16 in overall 2.4% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00407-x
• 作为产物：
  描述：

  (4aR,5R,6S)-6-tert-butyldimethylsilyloxy-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-2(3H)-naphthalenone 在 N-溴代丁二酰亚胺(NBS) 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 lithium carbonate 、 双(三甲基硅烷基)氨基钾 、 苯甲酸酐 、 2-(Phenylsulfonyl)-3-phenyloxaziridin 、 lithium bromide 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.0h， 生成 (3R,4aR,5R,6S)-4,4a,5,6-tetrahydro-6-hydroxy-4a,5-dimethyl-3-tetrahydropyranyloxy-2(3H)-naphthalenone
  参考文献：
  名称：

  Synthesis of dendryphiellin C, a trinor-sesquiterpene from a marine source

  摘要：

  Enantioselective synthesis of dendryphiellin C, isolated from cultures of Dendryphiella sarina, has been achieved in a convergent way such as coupling of a C9-branched carboxylic acid 10 with a trinor-eremophilane alcohol 11. The latter was synthesized starting from a chiral building block, (1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 16, which was originally prepared in this group using biochemical transformation as a key step. The synthesis was completed through 12 steps from 16 in overall 2.4% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00407-x

文献信息

• Synthesis of dendryphiellin C, a trinor-sesquiterpene from a marine source
  作者：Hiroko Akao、Hiromasa Kiyota、Takao Nakajima、Takeshi Kitahara

  DOI：10.1016/s0040-4020(99)00407-x

  日期：1999.6

  Enantioselective synthesis of dendryphiellin C, isolated from cultures of Dendryphiella sarina, has been achieved in a convergent way such as coupling of a C9-branched carboxylic acid 10 with a trinor-eremophilane alcohol 11. The latter was synthesized starting from a chiral building block, (1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 16, which was originally prepared in this group using biochemical transformation as a key step. The synthesis was completed through 12 steps from 16 in overall 2.4% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.