3-<4-<<(1',1'-dimethylethyl)dimethylsilyl>oxy>phenyl>prop-2-enyl bromide | 141222-05-1

• 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: 3-<4-<<(1',1'-dimethylethyl)dimethylsilyl>oxy>phenyl>prop-2-enyl bromide
• 英文别名: (E)-(4-(3-bromoprop-1-en-1-yl)phenoxy)(tert-butyl)dimethyl silane；[4-[(E)-3-bromoprop-1-enyl]phenoxy]-tert-butyl-dimethylsilane
• CAS: 141222-05-1
• 化学式: C₁₅H₂₃BrOSi
• 分子量: 327.337
• InChiKey: ZLRBNTNFFFJPGC-VOTSOKGWSA-N

物化性质

• 沸点：
  332.2±30.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  3-<4-<<(1',1'-dimethylethyl)dimethylsilyl>oxy>phenyl>prop-2-enyl bromide 在 四丁基氟化铵 、 sodium hydride 、 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Discovery of low nanomolar non-hydroxamate inhibitors of tumor necrosis factor-α converting enzyme (TACE)

  摘要：

  Using a pyrimidine-2,4,6-trione motif as a zinc-binding group, a series of selective inhibitors of tumor necrosis factor-alpha converting enzyme (TACE) was discovered. Optimization of initial lead I resulted in a potent inhibitor (51), with an IC50 of 2 nM in a porcine TACE assay. To the best of our knowledge, compound 51 and related analogues represent first examples of non-hydroxamate-based inhibitors of TACE with single digit nanomolar potency. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.048
• 作为产物：
  描述：

  4-香豆酸 在 咪唑 、 三溴化磷 、 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.33h， 生成 3-<4-<<(1',1'-dimethylethyl)dimethylsilyl>oxy>phenyl>prop-2-enyl bromide
  参考文献：
  名称：

  HIV-1 protease inhibitors based on hydroxyethylene dipeptide isosteres: An investigation into the role of the P1' side chain on structure-activity

  摘要：

  A systematic investigation was undertaken to determine the role of the P1' sidechain in a series of hydroxyethylene isostere based inhibitors of HIV-1 protease. Substitution and homologation of the benzyl P1' side chain of the Phe-Phe isostere based pseudo peptides 1 (L-682,679) and 2 (L-685,434) with various heteroalkyl groups leads to a series of extremely potent inhibitors of the enzyme. Several examples of the most potent inhibitors were very effective in an ex vivo cell based viral spread assay using human H9 T-lymphocytes and the IIIb isolate of HIV-1. Compound 19 is 120 times more potent than 1 and 16 times more potent than 2 in inhibiting the spread of infection in this assay.

  DOI：

  10.1021/jm00088a004

文献信息

• Barbituric acid derivatives as inhibitors of TNF-alpha converting enzyme (TACE) and/or matrix metalloproteinases
  申请人：——

  公开号：US20030229084A1

  公开（公告）日：2003-12-11

  The present application describes novel barbituric acid derivatives of formula I: 1 or pharmaceutically acceptable salt or prodrug forms thereof, wherein A, B, L, R 1 , R 2 , R 3 , R 4 , R 5 , n, W, U, X, Y, Z, U a , X a , Y a , and Z a are defined in the present specification, which are useful as TNF-&agr; converting enzyme (TACE) and matrix metalloproteinases (MMP) inhibitors.

  本申请描述了式I的新型巴比妥酸衍生物： 1 或其药用可接受的盐或前药形式，其中A、B、L、R 1 、R 2 、R 3 、R 4 、R 5 、n、W、U、X、Y、Z、U a 、X a 、Y a 和Z a 在本规范中定义，这些衍生物可用作TNF-α转化酶（TACE）和基质金属蛋白酶（MMP）抑制剂。
• Application of Solid Me₃SiZnI for the Synthesis of Aryl and Alkyl Trimethylsilanes
  作者：Anirban Ganguly、Revathi Chandrasekaran、Bala S. S. Balamurugan、Ramesh Rasappan

  DOI：10.1002/adsc.202301298

  日期：2024.3.19

  group compatibility renders silylzinc reagents desirable; however, their development is hindered by their synthesis using pyrophoric silyllithium and dissolved lithium salts. Our solid Me3SiZnI circumvents these limitations and herein, we demonstrate its significance in the cross-coupling of aryl and alkyl bromides.

  使用乙硅烷和甲硅烷基硼烷的过渡金属催化合成有机硅烷克服了传统氢化硅烷化的局限性。虽然乙硅烷需要特殊条件，但甲硅烷基硼烷尚未开发为 TMS 来源。官能团相容性使得硅锌试剂成为理想的选择；然而，它们的发展受到使用自燃硅基锂和溶解的锂盐合成的阻碍。我们的固体 Me3SiZnI 规避了这些限制，在此，我们证明了其在芳基溴和烷基溴交叉偶联中的重要性。
• HIV-1 protease inhibitors based on hydroxyethylene dipeptide isosteres: An investigation into the role of the P1' side chain on structure-activity
  作者：Steven D. Young、Linda S. Payne、Wayne J. Thompson、Neil Gaffin、Terry A. Lyle、Susan F. Britcher、Samuel L. Graham、Thomas H. Schultz、Albert A. Deana

  DOI：10.1021/jm00088a004

  日期：1992.5

  A systematic investigation was undertaken to determine the role of the P1' sidechain in a series of hydroxyethylene isostere based inhibitors of HIV-1 protease. Substitution and homologation of the benzyl P1' side chain of the Phe-Phe isostere based pseudo peptides 1 (L-682,679) and 2 (L-685,434) with various heteroalkyl groups leads to a series of extremely potent inhibitors of the enzyme. Several examples of the most potent inhibitors were very effective in an ex vivo cell based viral spread assay using human H9 T-lymphocytes and the IIIb isolate of HIV-1. Compound 19 is 120 times more potent than 1 and 16 times more potent than 2 in inhibiting the spread of infection in this assay.
• Discovery of low nanomolar non-hydroxamate inhibitors of tumor necrosis factor-α converting enzyme (TACE)
  作者：James J.-W. Duan、Lihua Chen、Zhonghui Lu、Bin Jiang、Naoyuki Asakawa、James E. Sheppeck、Rui-Qin Liu、Maryanne B. Covington、William Pitts、Soong-Hoon Kim、Carl P. Decicco

  DOI：10.1016/j.bmcl.2006.09.048

  日期：2007.1

  Using a pyrimidine-2,4,6-trione motif as a zinc-binding group, a series of selective inhibitors of tumor necrosis factor-alpha converting enzyme (TACE) was discovered. Optimization of initial lead I resulted in a potent inhibitor (51), with an IC50 of 2 nM in a porcine TACE assay. To the best of our knowledge, compound 51 and related analogues represent first examples of non-hydroxamate-based inhibitors of TACE with single digit nanomolar potency. (c) 2006 Elsevier Ltd. All rights reserved.