(2S,3S,4R)-2,7-Diethynyl-1-oxa-spiro[2.4]hept-6-en-4-ol | 691012-69-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (2S,3S,4R)-2,7-Diethynyl-1-oxa-spiro[2.4]hept-6-en-4-ol
• 英文别名: (2S,3S,7R)-2,4-diethynyl-1-oxaspiro[2.4]hept-4-en-7-ol
• CAS: 691012-69-8
• 化学式: C₁₀H₈O₂
• 分子量: 160.172
• InChiKey: HBXOVORHSFBUPA-UTLUCORTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-2,7-Diethynyl-1-oxa-spiro[2.4]hept-6-en-4-ol 、 (R)-3-(2-Chloro-3-hydroxy-4-methoxy-phenyl)-3-hydroxy-N-[(E)-3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide 在 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以50%的产率得到(R)-3-{2-Chloro-3-[(R)-1-((1S,5R)-2-ethynyl-1,5-dihydroxy-cyclopent-2-enyl)-prop-2-ynyloxy]-4-methoxy-phenyl}-3-hydroxy-N-[(E)-3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide
  参考文献：
  名称：

  Convergent approach to the maduropeptin chromophore: aryl ether formation of (R)-3-aryl-3-hydroxypropanamide and cyclization of macrolactam

  摘要：

  Efficient enantioselective syntheses of the functionalized phenol and diethynylcyclopentene moiety of the maduropeptin chromophore were achieved. Their CsF-mediated coupling yielded a sterically congested aryl propargyl ether. The subsequent intramolecular Sonogashira coupling reaction between the vinyl iodide and diethynyl groups occurred at the appropriate position to yield a macrolactam, which was accompanied by Pd-mediated enyne-yne benzarmulation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.020
• 作为产物：
  描述：

  (1S,2R,5S)-1-((R)-1-Bromo-3-trimethylsilanyl-prop-2-ynyl)-2-(tert-butyl-dimethyl-silanyloxy)-6-oxa-bicyclo[3.1.0]hexane 在 disodium hydrogenphosphate 、 正丁基锂 、 四丁基氟化铵 、 戴斯-马丁氧化剂 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 24.41h， 生成 (2S,3S,4R)-2,7-Diethynyl-1-oxa-spiro[2.4]hept-6-en-4-ol
  参考文献：
  名称：

  Convergent approach to the maduropeptin chromophore: aryl ether formation of (R)-3-aryl-3-hydroxypropanamide and cyclization of macrolactam

  摘要：

  Efficient enantioselective syntheses of the functionalized phenol and diethynylcyclopentene moiety of the maduropeptin chromophore were achieved. Their CsF-mediated coupling yielded a sterically congested aryl propargyl ether. The subsequent intramolecular Sonogashira coupling reaction between the vinyl iodide and diethynyl groups occurred at the appropriate position to yield a macrolactam, which was accompanied by Pd-mediated enyne-yne benzarmulation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.020