4-溴-3-乙基-9-戊-2-烯-4-炔基-2,8-二氧杂双环[5.2.1]癸烷-6-醇 | 36431-73-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 中文名称: 4-溴-3-乙基-9-戊-2-烯-4-炔基-2,8-二氧杂双环[5.2.1]癸烷-6-醇
• 英文名称: (-)-laurefucin
• 英文别名: Laurefucin；(1R,3R,4S,6R,7R,9R)-4-Bromo-3-ethyl-9-(2-penten-4-yn-1-yl)-2,8-dioxabicyclo[5.2.1]decan-6-ol；(1R,3R,4S,6R,7R,9R)-4-bromo-3-ethyl-9-[(E)-pent-2-en-4-ynyl]-2,8-dioxabicyclo[5.2.1]decan-6-ol
• CAS: 36431-73-9
• 化学式: C₁₅H₂₁BrO₃
• 分子量: 329.234
• InChiKey: NOYIFPKKLJWDFK-SIALDNDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-4-[(1R,3R,4S,6R,7R,9R)-4-bromo-3-ethyl-6-hydroxy-2,8-dioxabicyclo[5.2.1]decan-9-yl]but-2-enal 、 三甲基硅烷化重氮甲烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以85%的产率得到4-溴-3-乙基-9-戊-2-烯-4-炔基-2,8-二氧杂双环[5.2.1]癸烷-6-醇
  参考文献：
  名称：

  Biomimetic Asymmetric Total Synthesis of (−)-Laurefucin via an Organoselenium-Mediated Intramolecular Hydroxyetherification

  摘要：

  The first asymmetric total synthesis of (-)-laurefucin (1), a unique C-15 acetogenin with a 2,8-dioxabicyclo[5.2.1]decane skeleton, has been accomplished in nine steps in 31% overall yield from known oxocene 10. Highlights of the highly stereoselective synthesis include a novel organoselenium-mediated biomimetic hydroxyetherification.

  DOI：

  10.1021/ja806304s

文献信息

• Enzymatic Bromo-ether Cyclization of Laurediols with Bromoperoxidase
  作者：Akio Fukuzawa、Mya Aye、Yasunori Takasugi、Masao Nakamura、Mamoru Tamura、Akio Murai

  DOI：10.1246/cl.1994.2307

  日期：1994.12

  Natural (3E,6R,7R)- and (3Z,6S,7S)-laurediols were subjected to enzymatic reaction with the partially purified bromoperoxidase from the red alga, Laurencia nipponica, in the presence of H2O2 and NaBr to afford laurencin and prelaureatin, respectively. The further reaction of these products with bromoperoxidase gave rise to the bicyclic bromo-ethers.

  天然(3E,6R,7R)-和(3Z,6S,7S)-月桂醇在 H2O2 和 NaBr 的作用下，与部分纯化的红藻月桂过氧化物酶发生酶促反应，分别生成月桂苷和前月桂苷。这些产物与溴过氧化物酶的进一步反应生成了双环溴醚。
• Structure elucidation of laureoxanyne, a new nonisoprenoid C15 enyne, using lactoperoxidase
  作者：A. Fukuzawa、Mya Aye、M. Nakamura、M. Tanura、A. Murai

  DOI：10.1016/s0040-4039(00)97762-1

  日期：1990.1
• Biomimetic Asymmetric Total Synthesis of (−)-Laurefucin via an Organoselenium-Mediated Intramolecular Hydroxyetherification
  作者：Byungsook Kim、Miseon Lee、Mi Jung Kim、Hyunjoo Lee、Sanghee Kim、Deukjoon Kim、Minseob Koh、Seung Bum Park、Kye Jung Shin

  DOI：10.1021/ja806304s

  日期：2008.12.10

  The first asymmetric total synthesis of (-)-laurefucin (1), a unique C-15 acetogenin with a 2,8-dioxabicyclo[5.2.1]decane skeleton, has been accomplished in nine steps in 31% overall yield from known oxocene 10. Highlights of the highly stereoselective synthesis include a novel organoselenium-mediated biomimetic hydroxyetherification.