(5S,8R,10S)-9-vinylaustrodor-9-one | 676328-00-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5S,8R,10S)-9-vinylaustrodor-9-one
• 英文别名: 1-[(1R,3aS,7aS)-1,4,4,7a-tetramethyl-2,3,3a,5,6,7-hexahydroinden-1-yl]prop-2-en-1-one
• CAS: 676328-00-0
• 化学式: C₁₆H₂₆O
• 分子量: 234.382
• InChiKey: AMEUKAYDZUPMMA-RCBQFDQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (5S,8R,10S)-9-vinylaustrodor-9-one 在 sodium periodate 、 四氧化锇 作用下， 以 水 、 叔丁醇 为溶剂， 反应 12.0h， 以70%的产率得到(5S,8R,10S)-austrodoric acid
  参考文献：
  名称：

  Synthesis and absolute stereochemistry of marine nor-sesquiterpene austrodoric acid

  摘要：

  An enantiospecific synthesis of the nor-sesquiterpene austrodoric acid 1, recently isolated from an Antarctic marine mollusk, has been achieved. The synthetic strategy was based on the ring contraction of a suitable homo-drimanic epoxide,3, easily obtained from commercial (+)-sclareolide 4. The absolute configuration of natural austrodoric acid, not determined previously, has been now established by analyzing the CD profile of synthetic 1, which was the same as the natural compound. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.024
• 作为产物：
  描述：

  (5S,8R,10S)-9-(2-acetoxyethyl)-austrodor-9-one 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 苯 为溶剂， 反应 12.0h， 以95%的产率得到(5S,8R,10S)-9-vinylaustrodor-9-one
  参考文献：
  名称：

  基于频哪醇重排的澳大利亚多糖醇骨架的非对映选择性路线：(+)-澳大利亚多糖和(+)-澳大利亚多糖酸的合成

  摘要：

  摘要 描述了从劳丹烯二萜 (-)-香紫苏醇 (22) 到南芥骨架的有效途径。基于频哪醇重排的过程以完全的非对映选择性进行。利用这些，海洋去甲倍半萜 (+)-austrodoral (1) 和 (+)-austrodoric 酸 (2) 已由 22. 酮 19 制备，它是合成重排细胞毒性二萜内酯（如去甲缩松）的关键中间体(3)、也已制备成中等产量。

  DOI：

  10.1016/j.tet.2007.09.016

文献信息

• Diastereoselective routes towards the austrodorane skeleton based on pinacol rearrangement: synthesis of (+)-austrodoral and (+)-austrodoric acid
  作者：Enrique Alvarez-Manzaneda、Rachid Chahboun、Inmaculada Barranco、Eduardo Cabrera、Esteban Alvarez、Armando Lara、Ramón Alvarez-Manzaneda、Mohamed Hmamouchi、Hakima Es-Samti

  DOI：10.1016/j.tet.2007.09.016

  日期：2007.11

  Abstract Efficient routes towards the austrodorane skeleton from the labdane diterpene (−)-sclareol (22) are described. The processes, based on pinacol rearrangement, take place with complete diastereoselectivity. Utilizing these, the marine nor-sesquiterpenes (+)-austrodoral (1) and (+)-austrodoric acid (2) have been prepared from 22. Ketone 19, a key intermediate in the synthesis of rearranged cytotoxic

  摘要 描述了从劳丹烯二萜 (-)-香紫苏醇 (22) 到南芥骨架的有效途径。基于频哪醇重排的过程以完全的非对映选择性进行。利用这些，海洋去甲倍半萜 (+)-austrodoral (1) 和 (+)-austrodoric 酸 (2) 已由 22. 酮 19 制备，它是合成重排细胞毒性二萜内酯（如去甲缩松）的关键中间体(3)、也已制备成中等产量。
• Synthesis and absolute stereochemistry of marine nor-sesquiterpene austrodoric acid
  作者：Veaceslav Kulcitki、Nicon Ungur、Margherita Gavagnin、Marianna Carbone、Guido Cimino

  DOI：10.1016/j.tetasy.2003.10.024

  日期：2004.2

  An enantiospecific synthesis of the nor-sesquiterpene austrodoric acid 1, recently isolated from an Antarctic marine mollusk, has been achieved. The synthetic strategy was based on the ring contraction of a suitable homo-drimanic epoxide,3, easily obtained from commercial (+)-sclareolide 4. The absolute configuration of natural austrodoric acid, not determined previously, has been now established by analyzing the CD profile of synthetic 1, which was the same as the natural compound. (C) 2003 Elsevier Ltd. All rights reserved.