4-bromophenyl tert-butyl dimethylsilane | 188252-23-5

• 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: 4-bromophenyl tert-butyl dimethylsilane
• 英文别名: (4-Bromophenyl)-tert-butyl-dimethylsilane
• CAS: 188252-23-5
• 化学式: C₁₂H₁₉BrSi
• 分子量: 271.272
• InChiKey: WNRRKAWIXFXGAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  4-bromophenyl tert-butyl dimethylsilane 在 叔丁基锂 作用下， 以 正戊烷 为溶剂， 反应 4.5h， 以16.3%的产率得到
  参考文献：
  名称：

  Synthesis and Characterization of Lewis Base-Free, σ-Bonded Lithium Aryls:  A Structural Model for Unsolvated Phenyllithium in the Solid State

  摘要：

  The synthesis and characterization of four Lewis base-free, sigma-bonded lithium aryls are reported. This work was undertaken in order to provide a model for the solid-state structure of phenyllithium, which is currently unknown. Nondonor hydrocarbon solubility of the four lithium aryls (LiC6H3-3,5-t-Bu(2))(6) (1), (LiC6H4-4-t-Bu)(n) (2), (LiC6H4-4-n-Bu)(n) (3), and {LiC6H4-4-SiMe(2)(t-Bu)}(n) (4) was achieved by the incorporation of meta- or para-substituents on the aryl rings. This permitted C-13 NMR spectroscopy and crystal growth using their solutions. It is proposed that the absence of bulky ortho-substituents allows association of the Lithium aryls to occur in a manner similar to that of phenyllithium itself. The C-13 NMR data for the ipso-carbon atoms suggest an association number of at least four or, more probably, six in solution. These data are in agreement with the X-ray crystal structure of 1, which is hexameric, with a distorted octahedral (trigonal antiprismatic) array of lithium ions. Six of the eight Lis faces are capped by an aryl group that interacts primarily through the C(ipso) atom. Weaker Li-C(ortho) interactions are also apparent. This structure is the first of this type for an unsolvated, sigma-bonded Lithium aryl. Crystal data with Cu K alpha (lambda = 1.541 78 Angstrom) radiation for 1 at 130 K: 1, C84H126Li6, M = 1177.49, a = 13.516(2) Angstrom, b = 15.124(3) Angstrom, c = 20.958(3) Angstrom, alpha = 84.084(13)degrees, beta = 86.249(11) Angstrom, gamma = 68.675(13)degrees, V = 3967.7(11) Angstrom(3), Z = 2, space group , R(1) = 0.085 for 7983 (I > 2 sigma(I)) data.

  DOI：

  10.1021/ja962889i
• 作为产物：
  描述：

  [4-[Tert-butyl(dimethyl)silyl]phenyl]boronic acid 在 oxone||potassium monopersulfate triple salt 、 potassium bromide 、 copper(I) bromide 作用下， 以 乙腈 为溶剂， 以90 %的产率得到4-bromophenyl tert-butyl dimethylsilane
  参考文献：
  名称：

  芳基硼酸本身溴化的环保方案

  摘要：

  我们报告了一种利用 oxone/KBr 系统对芳基硼酸进行原位溴化的新颖且环保的方法。我们发现CuBr可以催化该反应并将产率从63%提高到97%。我们相信 CuBr 可能会催化 oxone/KBr原位生成 HOBr。温和的反应条件允许耐受多种官能团，具有独特的区域和化学选择性，并允许低成本的大规模反应，无爆炸风险。

  DOI：

  10.1021/acs.orglett.4c01570

文献信息

• Atroposelective Kinetic Resolution of 8<i>H</i>-Indeno[1,2-<i>c</i>]thiophen-8-ols via Pd-Catalyzed C–C Bond Cleavage Reaction
  作者：Junwei Xi、Han Yang、Lin Li、Xue Zhang、Chunyu Li、Zhenhua Gu

  DOI：10.1021/acs.orglett.2c00642

  日期：2022.4.1

  The present work demonstrates a palladium-catalyzed kinetic resolution/ring-opening reaction of 8H-indeno[1,2-c]thiophen-8-ols. The reaction proceeds in a highly regioselective manner, and both optically active thiophene-phenyl atropisomers and stereogenic 8H-indeno[1,2-c]thiophen-8-ols were obtained with high enantiomeric excesses. The synthetic applications of the obtained thiophenyl atropisomers

  本工作展示了钯催化的 8 H-茚并[1,2 - c ]噻吩-8-醇的动力学拆分/开环反应。该反应以高度区域选择性的方式进行，并且以高对映体过量获得了光学活性噻吩-苯基阻转异构体和立体异构 8 H-茚并[1,2 - c ]噻吩-8-醇。简要研究了所得噻吩阻转异构体的合成应用。
• 10.1021/acs.jafc.4c03001
  作者：Quan, Xiaocao、Shen, Kunkun、Yang, Wu-Lin、Li, Zhong、Maienfisch, Peter

  DOI：10.1021/acs.jafc.4c03001

  日期：——

  Bioisosteric silicon replacement has proven to be a valuable strategy in the design of bioactive molecules for crop protection and drug development. Twenty-one novel carboxamides possessing a silicon-containing biphenyl moiety were synthesized and tested for their antifungal activity and succinate dehydrogenase (SDH) enzymatic inhibitory activity. Among these novel succinate dehydrogenase inhibitors

  生物等排硅替代已被证明是作物保护和药物开发生物活性分子设计中的一种有价值的策略。合成了二十一种具有含硅联苯部分的新型甲酰胺，并测试了它们的抗真菌活性和琥珀酸脱氢酶（SDH）酶抑制活性。在这些新型琥珀酸脱氢酶抑制剂 (SDHI) 中，化合物3a 、 3e 、 4l和4o具有适当的c log P和拓扑极性表面积值，在 10 mg 剂量下对立枯丝核菌、核盘菌、灰葡萄孢和禾谷镰刀菌表现出优异的抑制效果/L体外， 4l和4o对立枯丝核菌的EC 50值分别为0.52和0.16 mg/L，对核盘菌的EC 50 值分别为0.066和0.054 mg/L，均优于啶酰菌胺。此外，化合物3a表现出优异的SDH酶抑制活性（IC 50 = 8.70 mg/L），其效力是啶酰菌胺的2.54倍（IC 50 = 22.09 mg/L）。对接结果和扫描电子显微镜实验揭示了化合物3a和啶酰菌胺之间相似的作用模式。新的含硅甲酰胺3a是一种有前途的
• [EN] HETEROCYCLE SUBSTITUTED CARBOXYLIC ACIDS AS INHIBITORS OF PROTEIN TYROSINE PHOSPHATASE-1B<br/>[FR] ACIDES CARBOXYLIQUES SUBSTITUES PAR DES HETEROCYCLES
  申请人：INST OF PHARMACEUTICAL DISCOVE

  公开号：WO2004099192A3

  公开（公告）日：2005-01-13
• JP2023/128945
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and Characterization of Lewis Base-Free, σ-Bonded Lithium Aryls:  A Structural Model for Unsolvated Phenyllithium in the Solid State
  作者：Rudolf J. Wehmschulte、Philip P. Power

  DOI：10.1021/ja962889i

  日期：1997.3.1

  The synthesis and characterization of four Lewis base-free, sigma-bonded lithium aryls are reported. This work was undertaken in order to provide a model for the solid-state structure of phenyllithium, which is currently unknown. Nondonor hydrocarbon solubility of the four lithium aryls (LiC6H3-3,5-t-Bu(2))(6) (1), (LiC6H4-4-t-Bu)(n) (2), (LiC6H4-4-n-Bu)(n) (3), and LiC6H4-4-SiMe(2)(t-Bu)}(n) (4) was achieved by the incorporation of meta- or para-substituents on the aryl rings. This permitted C-13 NMR spectroscopy and crystal growth using their solutions. It is proposed that the absence of bulky ortho-substituents allows association of the Lithium aryls to occur in a manner similar to that of phenyllithium itself. The C-13 NMR data for the ipso-carbon atoms suggest an association number of at least four or, more probably, six in solution. These data are in agreement with the X-ray crystal structure of 1, which is hexameric, with a distorted octahedral (trigonal antiprismatic) array of lithium ions. Six of the eight Lis faces are capped by an aryl group that interacts primarily through the C(ipso) atom. Weaker Li-C(ortho) interactions are also apparent. This structure is the first of this type for an unsolvated, sigma-bonded Lithium aryl. Crystal data with Cu K alpha (lambda = 1.541 78 Angstrom) radiation for 1 at 130 K: 1, C84H126Li6, M = 1177.49, a = 13.516(2) Angstrom, b = 15.124(3) Angstrom, c = 20.958(3) Angstrom, alpha = 84.084(13)degrees, beta = 86.249(11) Angstrom, gamma = 68.675(13)degrees, V = 3967.7(11) Angstrom(3), Z = 2, space group , R(1) = 0.085 for 7983 (I > 2 sigma(I)) data.