(S)-1-[(1S,2R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-6-oxa-bicyclo[3.1.0]hex-1-yl]-3-trimethylsilanyl-prop-2-yn-1-ol | 312328-76-0

• 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: (S)-1-[(1S,2R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-6-oxa-bicyclo[3.1.0]hex-1-yl]-3-trimethylsilanyl-prop-2-yn-1-ol
• 英文别名: (1S)-1-[(1S,2R,5S)-2-[tert-butyl(dimethyl)silyl]oxy-6-oxabicyclo[3.1.0]hexan-1-yl]-3-trimethylsilylprop-2-yn-1-ol
• CAS: 312328-76-0
• 化学式: C₁₇H₃₂O₃Si₂
• 分子量: 340.61
• InChiKey: FWEVSPFWGVTBFZ-MPTYRVRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-[(1S,2R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-6-oxa-bicyclo[3.1.0]hex-1-yl]-3-trimethylsilanyl-prop-2-yn-1-ol 在 disodium hydrogenphosphate 、 正丁基锂 、 四溴化碳 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 18.25h， 生成 (2S,3R,4S,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-2-trimethylsilanylethynyl-1-oxa-spiro[2.4]heptan-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
• 作为产物：
  描述：

  lithium trimethylsilylacetylenide 在 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (S)-1-[(1S,2R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-6-oxa-bicyclo[3.1.0]hex-1-yl]-3-trimethylsilanyl-prop-2-yn-1-ol
  参考文献：
  名称：

  Khan; Kato; Hirama, Synlett, 2000, # 10, p. 1494 - 1496

  摘要：

  DOI：

文献信息

• Convergent approach to the maduropeptin chromophore: aryl ether formation of (R)-3-aryl-3-hydroxypropanamide and cyclization of macrolactam
  作者：Nobuki Kato、Satoshi Shimamura、Safraz Khan、Fumiyo Takeda、Yoko Kikai、Masahiro Hirama

  DOI：10.1016/j.tet.2004.02.020

  日期：2004.3

  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.
• Khan; Kato; Hirama, Synlett, 2000, # 10, p. 1494 - 1496
  作者：Khan、Kato、Hirama

  DOI：——

  日期：——