(R)-1-[(R)-5-(tert-Butyl-dimethyl-silanyloxy)-cyclopent-1-enyl]-3-trimethylsilanyl-prop-2-yn-1-ol | 312328-75-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (R)-1-[(R)-5-(tert-Butyl-dimethyl-silanyloxy)-cyclopent-1-enyl]-3-trimethylsilanyl-prop-2-yn-1-ol
• 英文别名: (1R)-1-[(5R)-5-[tert-butyl(dimethyl)silyl]oxycyclopenten-1-yl]-3-trimethylsilylprop-2-yn-1-ol
• CAS: 312328-75-9
• 化学式: C₁₇H₃₂O₂Si₂
• 分子量: 324.611
• InChiKey: GBVJQAPSPIQEIS-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-1-[(R)-5-(tert-Butyl-dimethyl-silanyloxy)-cyclopent-1-enyl]-3-trimethylsilanyl-prop-2-yn-1-ol 在 4 A molecular sieve titanium(IV) isopropylate 、 叔丁基过氧化氢 、 disodium hydrogenphosphate 、 正丁基锂 、 L-(+)-酒石酸二乙酯 、 四溴化碳 、 戴斯-马丁氧化剂 、 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 33.08h， 生成 (2S,3R,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-2,4-bis-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：

  ((R)-2-Bromo-cyclopent-2-enyloxy)-tert-butyl-dimethyl-silane 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.33h， 生成 (R)-1-[(R)-5-(tert-Butyl-dimethyl-silanyloxy)-cyclopent-1-enyl]-3-trimethylsilanyl-prop-2-yn-1-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

文献信息

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

  DOI：——

  日期：——
• 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.