(1S,2S,4R,5R,6R)-6-bromo-4-<(S)-1-bromopropyl>-2-<(2Z)-5-(trimethylsilyl)-2-penten-4-ynyl>-3,8-dioxabicyclo<5.1.1>nonane | 141361-21-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环丁烷
• 英文名称: (1S,2S,4R,5R,6R)-6-bromo-4-<(S)-1-bromopropyl>-2-<(2Z)-5-(trimethylsilyl)-2-penten-4-ynyl>-3,8-dioxabicyclo<5.1.1>nonane
• 英文别名: [(Z)-5-[(1S,2S,4R,6R,7R)-6-bromo-4-[(1S)-1-bromopropyl]-3,8-dioxabicyclo[5.1.1]nonan-2-yl]pent-3-en-1-ynyl]-trimethylsilane
• CAS: 141361-21-9
• 化学式: C₁₈H₂₈Br₂O₂Si
• 分子量: 464.313
• InChiKey: DLQRGKQYKOHCBC-OAQSFCTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2S,4R,5R,6R)-6-bromo-4-<(S)-1-bromopropyl>-2-<(2Z)-5-(trimethylsilyl)-2-penten-4-ynyl>-3,8-dioxabicyclo<5.1.1>nonane 在 四丁基氟化铵 、 重水 、 溶剂黄146 、 锌 作用下， 以 乙醇 为溶剂， 反应 0.92h， 生成 (2S,3S,8R)-8-((S)-1-bromopropyl)-3-hydroxy-2-((2Z)-5-deuterio-2-penten-4-ynyl)-2,3,7,8-tetrahydrooxocine
  参考文献：
  名称：

  Conversion of prelaureatin into laurallene, a bromo-allene compound, by enzymatic and chemical bromo-etherification reactions

  摘要：

  Studies on biomimetic conversion of prelaureatin into laurallene were reported. This unique bromo-allene compound has been assumed to be biogenetically synthesized by bromo-cationic reaction of prelaureatin, an eight-membered ether, containing an enyne unit. The electrophilic bromination afforded laurallene chemically and enzymatically. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00542-5
• 作为产物：
  描述：

  三甲基氯硅烷 、 (1S,2S,4R,5R,6R)-6-bromo-4-<(S)-1-bromopropyl>-2-<(2Z)-2-penten-4-ynyl>-3,8-dioxabicyclo<5.1.1>nonane 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以89%的产率得到(1S,2S,4R,5R,6R)-6-bromo-4-<(S)-1-bromopropyl>-2-<(2Z)-5-(trimethylsilyl)-2-penten-4-ynyl>-3,8-dioxabicyclo<5.1.1>nonane
  参考文献：
  名称：

  Conversion of prelaureatin into laurallene, a bromo-allene compound, by enzymatic and chemical bromo-etherification reactions

  摘要：

  Studies on biomimetic conversion of prelaureatin into laurallene were reported. This unique bromo-allene compound has been assumed to be biogenetically synthesized by bromo-cationic reaction of prelaureatin, an eight-membered ether, containing an enyne unit. The electrophilic bromination afforded laurallene chemically and enzymatically. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00542-5

文献信息

• Isomerization of the (<i>Z</i>)-Enyne Unit to the (<i>E</i>)-Enyne Unit. Conversion of Laureatin to (<i>E</i>)-Isolaureatin
  作者：Jun Ishihara、Naoki Kanoh、Akio Fukuzawa、Akio Murai

  DOI：10.1246/cl.1994.1563

  日期：1994.8

  The (Z)-enyne compound bearing the acetylene part protected with dicobalt octacarbonyl, derived from laureatin, was reacted with trifluoromethanesulfonic acid to afford exclusively the corresponding (E)-derivative related to (E)-isolaureatin.

  带有由月桂醛衍生的八羰基二钴保护的乙炔部分的 (Z)-烯炔化合物与三氟甲磺酸反应以专门提供与 (E)-异月桂醛相关的相应 (E)-衍生物。
• Enzymatic reaction of (3E,6S,7S)-laurediol and the molecular modeling studies on the cyclization of laurediols
  作者：Jun Ishihara、Naoki Kanoh、Akio Murai

  DOI：10.1016/0040-4039(94)02329-a

  日期：1995.1

  The biosynthetic reaction of (3E,6S,7S)-laurediol with H2O2 and NaBr by lactoperoxidase afforded (E)-prelaureation. The molecular modeling studies on the bromo-ether cyclization reactions of laurediols are also described.
• Conversion of prelaureatin into laurallene, a bromo-allene compound, by enzymatic and chemical bromo-etherification reactions
  作者：Jun Ishihara、Yoshikatsu Shimada、Naoki Kanoh、Yasunori Takasugi、Akio Fukuzawa、Akio Murai

  DOI：10.1016/s0040-4020(97)00542-5

  日期：1997.6

  Studies on biomimetic conversion of prelaureatin into laurallene were reported. This unique bromo-allene compound has been assumed to be biogenetically synthesized by bromo-cationic reaction of prelaureatin, an eight-membered ether, containing an enyne unit. The electrophilic bromination afforded laurallene chemically and enzymatically. (C) 1997 Elsevier Science Ltd.