(4aS,6R,8aR,12aS,13aR)-6-Bromo-tetradecahydro-4,9,13-trioxa-dibenzo[a,d]cyclononene | 250140-11-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (4aS,6R,8aR,12aS,13aR)-6-Bromo-tetradecahydro-4,9,13-trioxa-dibenzo[a,d]cyclononene
• 英文别名: (1S,3R,8S,10R,13R)-10-bromo-2,7,14-trioxatricyclo[11.4.0.03,8]heptadecane
• CAS: 250140-11-5
• 化学式: C₁₄H₂₃BrO₃
• 分子量: 319.239
• InChiKey: MXAOILATPHUJFL-RGDJUOJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4aS,6R,8aR,12aS,13aR)-6-Bromo-tetradecahydro-4,9,13-trioxa-dibenzo[a,d]cyclononene 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 生成 (1R,3S,8R,13S)-2,7,14-trioxatricyclo[11.4.0.0^3,8]heptadec-10-ene
  参考文献：
  名称：

  Construction of fused oxonene ring and reproduction of conformational behavior shown by ring F of ciguatoxin

  摘要：

  trans-Fused 6-9-6 tricyclic ether 2 was synthesized and conformational alternation of the oxonene ring was reproduced as was observed for that in the ciguatoxin molecule (ring F). SmI2-promoted intramolecular Reformatsky reaction of O-linked bicyclic compound 4 features the construction of an oxonane ring in the present synthesis. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00125-1
• 作为产物：
  描述：

  (1R,3S,8S,11R,13S)-11-acetoxy-2,7,14-trioxatricyclo[11.4.0.0^3,8]heptadecan-9-one 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 偶氮二异丁腈 、 三正丁基氢锡 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 、 lithium bromide 、 甲基磺酸酐 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 2.84h， 生成 (4aS,6R,8aR,12aS,13aR)-6-Bromo-tetradecahydro-4,9,13-trioxa-dibenzo[a,d]cyclononene
  参考文献：
  名称：

  所述的汇集合成反式由雪卡毒素的环F所示-融合hexahydrooxonine环系统和构象行为再现

  摘要：

  已经开发出用于构造稠合六氢氧肟酸环系统的新策略。本发明涉及γ-烷氧基烯丙基硅烷与乙缩醛的分子内反应以形成O-连接的氧杂环和SmI 2介导的分子内Reformatsky反应，用于构建氧杂环丁烷环是关键步骤。如在雪茄毒素分子（环F）中所观察到的那样，首次澄清了转熔合六氢氧肟酸环的热力学行为，并且在6-9-6三环模型化合物1中复制了构象交替。

  DOI：

  10.1016/s0040-4020(99)00620-1

文献信息

• A convergent synthesis of the trans-fused hexahydrooxonine ring system and reproduction of conformational behavior shown by ring F of ciguatoxin
  作者：Masayuki Inoue、Makoto Sasaki、Kazuo Tachibana

  DOI：10.1016/s0040-4020(99)00620-1

  日期：1999.9

  hexahydrooxonine ring system has been developed. The present synthesis involves an intramolecular reaction of γ-alkoxyallylsilane with acetal to form an O-linked oxacycle and a SmI2-mediated intramolecular Reformatsky reaction for constructing an oxonane ring as the key steps. Thermodynamic behavior of the trans-fused hexahydrooxonine ring was clarified for the first time and the conformational alternation

  已经开发出用于构造稠合六氢氧肟酸环系统的新策略。本发明涉及γ-烷氧基烯丙基硅烷与乙缩醛的分子内反应以形成O-连接的氧杂环和SmI 2介导的分子内Reformatsky反应，用于构建氧杂环丁烷环是关键步骤。如在雪茄毒素分子（环F）中所观察到的那样，首次澄清了转熔合六氢氧肟酸环的热力学行为，并且在6-9-6三环模型化合物1中复制了构象交替。
• Construction of fused oxonene ring and reproduction of conformational behavior shown by ring F of ciguatoxin
  作者：Masayuki Inoue、Makoto Sasaki、Kazuo Tachibana

  DOI：10.1016/s0040-4039(97)00125-1

  日期：1997.3

  trans-Fused 6-9-6 tricyclic ether 2 was synthesized and conformational alternation of the oxonene ring was reproduced as was observed for that in the ciguatoxin molecule (ring F). SmI2-promoted intramolecular Reformatsky reaction of O-linked bicyclic compound 4 features the construction of an oxonane ring in the present synthesis. (C) 1997 Elsevier Science Ltd.