tert-butyl(3-ethynylphenoxy)diphenylsilane | 1203611-09-9

• 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: tert-butyl(3-ethynylphenoxy)diphenylsilane
• 英文别名: 3-[(tert-butyldiphenyl)silanyloxy]phenylacetylene；Tert-butyl-(3-ethynylphenoxy)-diphenylsilane
• CAS: 1203611-09-9
• 化学式: C₂₄H₂₄OSi
• 分子量: 356.539
• InChiKey: DCRRTPXHTHZHQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  tert-butyl(3-ethynylphenoxy)diphenylsilane 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 (S,S)-2,2'-异亚丙基双(4-苯基-2-恶唑啉) 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 ethyl (1R,2S,3S)-2-(3-((tert-butyldiphenylsilyl)oxy)phenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropane-1-carboxylate
  参考文献：
  名称：

  1-烯基硼酸酯的对映和非对映选择性环丙烷化：1-Boryl-2,3-二取代环丙烷的合成

  摘要：

  在催化量的手性铜（I）络合物的存在下，通过烯基硼酸酯与重氮乙酸乙酯的环丙烷化反应，开发出了一种新型的，对映体和非对映体选择性高的1-硼基-2,3-二取代环丙烷。还可以通过操作简单，顺序的硼氢化-环丙烷化协议从炔烃中直接访问该产品。所得的对映体富集的1-硼基-2,3-二取代的环丙烷是通用的合成中间体，在碳-硼键处进行进一步的转化。

  DOI：

  10.1002/anie.201710415
• 作为产物：
  描述：

  3-羟基苯基乙炔 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到tert-butyl(3-ethynylphenoxy)diphenylsilane
  参考文献：
  名称：

  Rational Design of 5-Phenyl-3-isoxazolecarboxylic Acid Ethyl Esters as Growth Inhibitors of Mycobacterium tuberculosis. A Potent and Selective Series for Further Drug Development

  摘要：

  New antituberculosis (anti-TB) drugs are urgently needed to shorten the 6-12 month treatment regimen and especially to battle drug-resistant Mycobacterium tuberculosis (Mtb) strains. In this study, we have continued our efforts to develop isoxazole-based anti-TB compounds by applying rational drug design approach. The biological activity and the structure-activity relationships (SAR) for a designed series of 5-phenyl-3-isoxazolecarboxylic acid ethyl ester derived anti-TB compounds were investigated. Several compounds were found to exhibit nanomolar activity against the replicating bacteria (R-TB) and low micromolar activity against the nonreplicating bacteria (NRP-TB). The series showed excellent selectivity toward Mtb, and in general, no cytotoxicity was observed in Vero cells (IC50 > 128 mu M). Notably, selected compounds also retained their activity against isoniazid (INH), rifampin (RMP), and streptomycin (SM) resistant Mtb strains. Hence, benzyloxy, benzylamino, and phenoxy derivatives of 5-phenyl-3-isoxazolecarboxylic acid ethyl esters represent a highly potent, selective, and versatile series of anti-TB compounds and as Such present attractive lead compounds for further TB drug development.

  DOI：

  10.1021/jm901273n

文献信息

• Oxidize Amines to Nitrile Oxides: One Type of Amine Oxidation and Its Application to Directly Construct Isoxazoles and Isoxazolines
  作者：Xiao-Wei Zhang、Xiao-Lin He、Nan Yan、Hong-Xing Zheng、Xiang-Guo Hu

  DOI：10.1021/acs.joc.0c02281

  日期：2020.12.4

  A facile oxidative heterocyclization of commercially available amines and tert-butyl nitrite with alkynes or alkenes leading to isoxazoles or isoxazolines is described. The unprecedented strategy of the oxidation of an amine directly to a nitrile oxide was used in this cyclization process. This reaction is highly efficient, regiospecific, operationally simple, mild, and tolerant of a variety of functional

  描述了可商购的胺和亚硝酸叔丁酯与炔或烯烃的容易的氧化性杂环化，其导致异恶唑或异恶唑啉。在这种环化过程中使用了前所未有的将胺直接氧化为一氧化氮的策略。该反应是高效的，区域特异性的，操作简单的，温和的，并且耐受多种官能团。对照实验为这种新型的氧化环化反应提供了一种一氧化氮中间体机制。此外，实现了对生物活性分子骨架的合成应用和药物的后期修饰。
• Cu-Catalyzed Synthesis of Fluoroalkylated Isoxazoles from Commercially Available Amines and Alkynes
  作者：Xiao-Wei Zhang、Wen-Li Hu、Suo Chen、Xiang-Guo Hu

  DOI：10.1021/acs.orglett.7b04028

  日期：2018.2.2

  A one-pot protocol for the construction of fluoroalkylated isoxazoles directly from commercially available amines and alkynes is described. The reaction is scalable, operationally simple, regioselective, mild, and tolerant of a broad range of functional groups. As such, it could be viewed as a “click synthesis” of fluoroalkylated isoxazoles. Preliminary mechanistic investigations reveal that the transformation

  描述了一种直接从市售胺和炔烃构建氟代烷基化异恶唑的一锅法操作规程。该反应是可扩展的，操作简单的，区域选择性的，温和的，并且耐受多种官能团。因此，可以将其视为氟代烷基化异恶唑的“点击合成”。初步的机械研究表明，该转化涉及涉及R f CHN 2的空前的Cu催化级联序列。
• Rational Design of 5-Phenyl-3-isoxazolecarboxylic Acid Ethyl Esters as Growth Inhibitors of <i>Mycobacterium tuberculosis</i>. A Potent and Selective Series for Further Drug Development
  作者：Annamaria Lilienkampf、Marco Pieroni、Baojie Wan、Yuehong Wang、Scott G. Franzblau、Alan P. Kozikowski

  DOI：10.1021/jm901273n

  日期：2010.1.28

  New antituberculosis (anti-TB) drugs are urgently needed to shorten the 6-12 month treatment regimen and especially to battle drug-resistant Mycobacterium tuberculosis (Mtb) strains. In this study, we have continued our efforts to develop isoxazole-based anti-TB compounds by applying rational drug design approach. The biological activity and the structure-activity relationships (SAR) for a designed series of 5-phenyl-3-isoxazolecarboxylic acid ethyl ester derived anti-TB compounds were investigated. Several compounds were found to exhibit nanomolar activity against the replicating bacteria (R-TB) and low micromolar activity against the nonreplicating bacteria (NRP-TB). The series showed excellent selectivity toward Mtb, and in general, no cytotoxicity was observed in Vero cells (IC50 > 128 mu M). Notably, selected compounds also retained their activity against isoniazid (INH), rifampin (RMP), and streptomycin (SM) resistant Mtb strains. Hence, benzyloxy, benzylamino, and phenoxy derivatives of 5-phenyl-3-isoxazolecarboxylic acid ethyl esters represent a highly potent, selective, and versatile series of anti-TB compounds and as Such present attractive lead compounds for further TB drug development.
• Enantio- and Diastereoselective Cyclopropanation of 1-Alkenylboronates: Synthesis of 1-Boryl-2,3-Disubstituted Cyclopropanes
  作者：Javier Carreras、Ana Caballero、Pedro J. Pérez

  DOI：10.1002/anie.201710415

  日期：2018.2.23

  A novel, highly enantio‐ and diastereoselective synthesis of 1‐boryl‐2,3‐disubstituted cyclopropanes has been developed by means of the cyclopropanation of alkenylboronates with ethyl diazoacetate in the presence of catalytic amounts of a chiral copper(I) complex. The products can also be directly accessed from alkynes through an operationally simple, sequential hydroboration–cyclopropanation protocol

  在催化量的手性铜（I）络合物的存在下，通过烯基硼酸酯与重氮乙酸乙酯的环丙烷化反应，开发出了一种新型的，对映体和非对映体选择性高的1-硼基-2,3-二取代环丙烷。还可以通过操作简单，顺序的硼氢化-环丙烷化协议从炔烃中直接访问该产品。所得的对映体富集的1-硼基-2,3-二取代的环丙烷是通用的合成中间体，在碳-硼键处进行进一步的转化。