{(Z)-5-[(1S,3R,5S,6S,8S)-5-Bromo-3-((S)-1-bromo-propyl)-2,7-dioxa-bicyclo[4.2.1]non-8-yl]-pent-3-en-1-ynyl}-trimethyl-silane | 612051-03-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: {(Z)-5-[(1S,3R,5S,6S,8S)-5-Bromo-3-((S)-1-bromo-propyl)-2,7-dioxa-bicyclo[4.2.1]non-8-yl]-pent-3-en-1-ynyl}-trimethyl-silane
• 英文别名: [(Z)-5-[(1S,3R,5S,6S,8S)-5-bromo-3-[(1S)-1-bromopropyl]-2,7-dioxabicyclo[4.2.1]nonan-8-yl]pent-3-en-1-ynyl]-trimethylsilane
• CAS: 612051-03-3
• 化学式: C₁₈H₂₈Br₂O₂Si
• 分子量: 464.313
• InChiKey: DXJUEUXCWQOANG-WAMKZPEQSA-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：
  2.0
• 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：

  {(Z)-5-[(1S,3R,5S,6S,8S)-5-Bromo-3-((S)-1-bromo-propyl)-2,7-dioxa-bicyclo[4.2.1]non-8-yl]-pent-3-en-1-ynyl}-trimethyl-silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以97%的产率得到(+)-neoisoprelaurefucin
  参考文献：
  名称：

  Total synthesis and determination of the absolute configuration of (+)-neoisoprelaurefucin

  摘要：

  The first total synthesis of the seven-membered ring ether marine natural product (+)-neoisoprelaurefucin (1) has been achieved employing a regioselective internal alkylation of amide 3, a novel sequence for removal of the triethylsilyl group from the resulting triethylsilyloxepene 2, and a bromoetherification of alcohol 16 as key steps. In addition, the absolute stereochemistry of the natural product was assigned. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/s0040-4039(03)01667-8
• 作为产物：
  描述：

  (E)-(3S,4S)-1-Benzyloxy-3-(4-methoxy-benzyloxy)-8-(tetrahydro-pyran-2-yloxy)-6-triethylsilanyl-oct-6-en-4-ol 在 palladium on activated charcoal 、 四(三苯基膦)钯 四氯化碳 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 3-甲基-1-环己烯 、 四溴化碳 、 三辛基膦 、 potassium tert-butylate 、 氢气 、 三正丁基氢锡 、 双(三甲基硅烷基)氨基钾 、 sodium hydride 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 二乙胺 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 alkaline aq. solution 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 41.0h， 生成 {(Z)-5-[(1S,3R,5S,6S,8S)-5-Bromo-3-((S)-1-bromo-propyl)-2,7-dioxa-bicyclo[4.2.1]non-8-yl]-pent-3-en-1-ynyl}-trimethyl-silane
  参考文献：
  名称：

  Total synthesis and determination of the absolute configuration of (+)-neoisoprelaurefucin

  摘要：

  The first total synthesis of the seven-membered ring ether marine natural product (+)-neoisoprelaurefucin (1) has been achieved employing a regioselective internal alkylation of amide 3, a novel sequence for removal of the triethylsilyl group from the resulting triethylsilyloxepene 2, and a bromoetherification of alcohol 16 as key steps. In addition, the absolute stereochemistry of the natural product was assigned. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/s0040-4039(03)01667-8

文献信息

• Total synthesis and determination of the absolute configuration of (+)-neoisoprelaurefucin
  作者：Hyunjoo Lee、Hyoungsu Kim、Seungyoup Baek、Sanghee Kim、Deukjoon Kim

  DOI：10.1016/s0040-4039(03)01667-8

  日期：2003.8

  The first total synthesis of the seven-membered ring ether marine natural product (+)-neoisoprelaurefucin (1) has been achieved employing a regioselective internal alkylation of amide 3, a novel sequence for removal of the triethylsilyl group from the resulting triethylsilyloxepene 2, and a bromoetherification of alcohol 16 as key steps. In addition, the absolute stereochemistry of the natural product was assigned. (C) 2003 Published by Elsevier Ltd.