5-(tert-butyldimethylsiloxy)-1-ethynyloxy-2-(p-methoxybenzyloxy)-pentane | 1375645-17-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(tert-butyldimethylsiloxy)-1-ethynyloxy-2-(p-methoxybenzyloxy)-pentane
• 英文别名: Tert-butyl-[5-ethynoxy-4-[(4-methoxyphenyl)methoxy]pentoxy]-dimethylsilane
• CAS: 1375645-17-2
• 化学式: C₂₁H₃₄O₄Si
• 分子量: 378.584
• InChiKey: BQLZEEQENKWAMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.99
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(tert-butyldimethylsiloxy)-1-ethynyloxy-2-(p-methoxybenzyloxy)-pentane 在 bis-triphenylphosphine-palladium(II) chloride 、 四丁基氟化铵 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 ethyl 3-[4-[(E)-2-[5-hydroxy-2-[(4-methoxyphenyl)methoxy]pentoxy]ethenyl]furan-3-yl]propanoate
  参考文献：
  名称：

  Toward the total synthesis of Luminamicin: construction of 14-membered lactone framework possessing versatile enol ether moiety

  摘要：

  Luminamicin (1) was found to exhibit selective antibacterial activity against anaerobic bacteria by our group in 1985. The concise structure of 14-membered lactone of 1 was synthesized. Construction of a versatile enol ether moiety was achieved by Stille cross coupling via hydrostanylation of the ethynyl ether, and a maleic anhydride moiety was derived from the furan constitution by the oxidation after the macrolactonization at a late-stage. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.03.098
• 作为产物：
  描述：

  三氯乙烯 、 5-[Tert-butyl(dimethyl)silyl]oxy-2-[(4-methoxyphenyl)methoxy]pentan-1-ol 在 potassium hydride 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以97%的产率得到5-(tert-butyldimethylsiloxy)-1-ethynyloxy-2-(p-methoxybenzyloxy)-pentane
  参考文献：
  名称：

  Toward the total synthesis of Luminamicin: construction of 14-membered lactone framework possessing versatile enol ether moiety

  摘要：

  Luminamicin (1) was found to exhibit selective antibacterial activity against anaerobic bacteria by our group in 1985. The concise structure of 14-membered lactone of 1 was synthesized. Construction of a versatile enol ether moiety was achieved by Stille cross coupling via hydrostanylation of the ethynyl ether, and a maleic anhydride moiety was derived from the furan constitution by the oxidation after the macrolactonization at a late-stage. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.03.098

文献信息

• Pd-catalyzed Regio- and Stereoselective Hydrostannylation of an Alkyl Ethynyl Ether/One-Pot Stille Coupling Enables the Synthesis of 14-Membered Macrolactone of Luminamicin
  作者：Akihiro Sugawara、Hirokazu Takada、Tomoyasu Hirose、Aoi Kimishima、Takeshi Yamada、Masaki Toda、Toru Kojima、Takanori Matsumaru、Toshiaki Sunazuka

  DOI：10.1021/acs.orglett.1c00183

  日期：2021.3.5

  Regio- and stereoselective hydrostannylation of alkyl ethynyl ethers generates alkenyl ethers, which are useful building blocks in organic synthesis. This efficient synthetic method, however, is limited. Here, we report not only an efficient method for a highly regio- and stereoselective Pd-catalyzed hydrostannylation of alkyl ethynyl ethers but also a scalable synthesis and construction of the core

  烷基乙炔基醚的区域和立体选择性加氢苯乙烯基化反应生成烯基醚，这是有机合成中有用的组成部分。但是，这种有效的合成方法受到限制。在这里，我们不仅报告了一种高效的方法，用于烷基乙炔基醚的高度区域选择性和立体选择性的Pd催化加氢苯乙烯基化反应，而且还报道了具有所有功能基团和​​立体中心的luminamicin核心框架的可扩展合成和构建。