tert-butyl {[(3E)-4-(4-methoxyphenyl)but-3-enyl]oxy}dimethylsilane | 689258-74-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tert-butyl {[(3E)-4-(4-methoxyphenyl)but-3-enyl]oxy}dimethylsilane
• 英文别名: (E)-tert-butyl((4-(4-methoxyphenyl)but-3-en-1-yl)oxy)dimethylsilane；tert-butyl-[(E)-4-(4-methoxyphenyl)but-3-enoxy]-dimethylsilane
• CAS: 689258-74-0
• 化学式: C₁₇H₂₈O₂Si
• 分子量: 292.494
• InChiKey: XUMUFMMDPXQLFB-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl {[(3E)-4-(4-methoxyphenyl)but-3-enyl]oxy}dimethylsilane 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 以 正己烷 、 三溴甲烷 、 水 为溶剂， 生成 2-[2,2-dibromo-3-(4-methoxyphenyl)cyclopropyl]ethanol
  参考文献：
  名称：

  Cycloalkyl alkanoic acids as integrin receptor antagonists derivatives

  摘要：

  本发明涉及一类由化学式I表示的化合物，或其药学上可接受的盐，包括化合物I的药物组合物，以及选择性地抑制或拮抗αvβ3和/或αvβ5整合素的方法。

  公开号：

  US06921767B2
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 咪唑 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 tert-butyl {[(3E)-4-(4-methoxyphenyl)but-3-enyl]oxy}dimethylsilane
  参考文献：
  名称：

  Discovery of +(2-{4-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]phenyl}-cyclopropyl)acetic acid as potent and selective αvβ3 inhibitor: Design, synthesis, and optimization

  摘要：

  The integrin alpha(v)beta(3) is expressed in a number of cell types and is thought to play a major role in several pathological conditions. Various small molecules that inhibit the integrin have been shown to suppress tumor growth and retinal angiogenesis. The tripeptide Arg-Gly-Asp (RGD), a common binding motif in several ligands that bind to alpha(v)beta(3), has been depeptidized and optimized in our efforts toward discovering a small molecule inhibitor. We recently disclosed the synthesis and biological activity of several small molecules that did not contain any peptide bond and mimic the tripeptide RGD. The phenethyl group in one of the lead compounds was successfully replaced with a cyclopropyl moiety. The new lead compound was optimized for potency, selectivity, and for its ADME properties. We describe herein the discovery, synthesis, and optimization of cyclopropyl containing analogs that are potent and selective inhibitors of alpha(v)beta(3). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.03.020

文献信息

• Palladium-Catalyzed Allylic Cross-Coupling Reactions of Primary and Secondary Homoallylic Electrophiles
  作者：Benjamin J. Stokes、Susanne M. Opra、Matthew S. Sigman

  DOI：10.1021/ja305403s

  日期：2012.7.18

  cross-coupling of homoallylic tosylate substrates using boronic acids and pinacol esters is reported. The reaction uses 2-(4,5-dihydro-2-oxazolyl)quinoline (quinox) as a ligand and is performed at ambient temperature. The scope of the reaction is broad in terms of both the boronate transmetalating reagent and the substrate and includes secondary tosylates. Mechanistic studies support an alkene-mediated

  报道了使用硼酸和频哪醇酯的 Pd(0) 催化的高烯丙基甲苯磺酸酯底物的烯丙基交叉偶联。该反应使用 2-(4,5-二氢-2-恶唑基) 喹啉 (quinox) 作为配体并在环境温度下进行。就硼酸盐金属转移试剂和底物而言，反应范围很广，包括甲苯磺酸仲酯。机理研究支持未活化的初级和次级烷基甲苯磺酸盐的烯烃介导的 S(N)2 型立体转化氧化加成。
• Stereoselective Copper‐Catalyzed Olefination of Imines
  作者：James E. Baumann、Crystal P. Chung、Gojko Lalic

  DOI：10.1002/anie.202316521

  日期：2024.2.5

  A new look at catalytic Wittig-type olefinations. We explored the use of transition metal catalysis to form ylide equivalents from readily available starting materials leading to the development of a highly E-selective copper-catalyzed olefination of imines with alkenyl boronate esters as coupling partners.

  催化维蒂希型烯化反应的新视角。我们探索了使用过渡金属催化从容易获得的起始材料形成叶立德等价物，从而开发出以烯基硼酸酯作为偶联伙伴的高E选择性铜催化亚胺烯化反应。
• Cycloalkyl alkanoic acids as integrin receptor antagonists derivatives
  申请人：——

  公开号：US20040092538A1

  公开（公告）日：2004-05-13

  The present invention relates to a class of compounds represented by the Formula I 1 or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising compounds of the Formula I, and methods of selectively inhibiting or antagonizing the &agr; v &bgr; 3 and/or &agr; v &bgr; 5 integrin.

  本发明涉及一类由公式I代表的化合物 1 或其药用可接受的盐，包含公式I化合物的药物组合物，以及选择性地抑制或拮抗α v β 3 和/或α v β 5 整合素的方法。
• Discovery of +(2-{4-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]phenyl}-cyclopropyl)acetic acid as potent and selective αvβ3 inhibitor: Design, synthesis, and optimization
  作者：Srinivasan R. Nagarajan、Hwang-Fun Lu、Alan F. Gasiecki、Ish K. Khanna、Mihir D. Parikh、Bipinchandra N. Desai、Thomas E. Rogers、Michael Clare、Barbara B. Chen、Mark A. Russell、Jeffery L. Keene、Tiffany Duffin、V. Wayne Engleman、Mary B. Finn、Sandra K. Freeman、Jon A. Klover、G. Alan Nickols、Maureen A. Nickols、Kristen E. Shannon、Christina A. Steininger、William F. Westlin、Marisa M. Westlin、Melanie L. Williams

  DOI：10.1016/j.bmc.2007.03.020

  日期：2007.5

  The integrin alpha(v)beta(3) is expressed in a number of cell types and is thought to play a major role in several pathological conditions. Various small molecules that inhibit the integrin have been shown to suppress tumor growth and retinal angiogenesis. The tripeptide Arg-Gly-Asp (RGD), a common binding motif in several ligands that bind to alpha(v)beta(3), has been depeptidized and optimized in our efforts toward discovering a small molecule inhibitor. We recently disclosed the synthesis and biological activity of several small molecules that did not contain any peptide bond and mimic the tripeptide RGD. The phenethyl group in one of the lead compounds was successfully replaced with a cyclopropyl moiety. The new lead compound was optimized for potency, selectivity, and for its ADME properties. We describe herein the discovery, synthesis, and optimization of cyclopropyl containing analogs that are potent and selective inhibitors of alpha(v)beta(3). (c) 2007 Elsevier Ltd. All rights reserved.