4-[(dimethyl-tert-butyl-silyl)thio]-phenylboronic acid | 237429-34-4

• 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-[(dimethyl-tert-butyl-silyl)thio]-phenylboronic acid
• 英文别名: Boronic acid, [4-[[(1,1-dimethylethyl)dimethylsilyl]thio]phenyl]-；[4-[tert-butyl(dimethyl)silyl]sulfanylphenyl]boronic acid
• CAS: 237429-34-4
• 化学式: C₁₂H₂₁BO₂SSi
• 分子量: 268.26
• InChiKey: LVWAECQNRQHDRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(dimethyl-tert-butyl-silyl)thio]-phenylboronic acid 在 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 4-甲硫基苯硼酸
  参考文献：
  名称：

  Boronated thiophenols: a preparation of 4-mercaptophenylboronic acid and derivatives

  摘要：

  4-Mercaptophenylboronic acid derivatives were prepared by a metallation/boration sequence from S-protected 3-bromothiophenols; the t-butyldimethylsilylthioether was found suitable to allow subsequent regeneration of the mercapto group after boration. The parent compound, 4-mercaptophenylboronic acid, could thus be obtained and was subsequently S-alkylated; 4-boronophenylthioacetic acid was prepared without the need to protect the boronic acid group. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(99)00086-8
• 作为产物：
  描述：

  (4-溴苯基硫代)二甲基叔丁基硅烷 在 正丁基锂 、 硼酸三异丙酯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.25h， 以77%的产率得到4-[(dimethyl-tert-butyl-silyl)thio]-phenylboronic acid
  参考文献：
  名称：

  Boronated thiophenols: a preparation of 4-mercaptophenylboronic acid and derivatives

  摘要：

  4-Mercaptophenylboronic acid derivatives were prepared by a metallation/boration sequence from S-protected 3-bromothiophenols; the t-butyldimethylsilylthioether was found suitable to allow subsequent regeneration of the mercapto group after boration. The parent compound, 4-mercaptophenylboronic acid, could thus be obtained and was subsequently S-alkylated; 4-boronophenylthioacetic acid was prepared without the need to protect the boronic acid group. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(99)00086-8

文献信息

• Boronated thiophenols: a preparation of 4-mercaptophenylboronic acid and derivatives
  作者：Abdelghani Brikh、Christophe Morin

  DOI：10.1016/s0022-328x(99)00086-8

  日期：1999.6

  4-Mercaptophenylboronic acid derivatives were prepared by a metallation/boration sequence from S-protected 3-bromothiophenols; the t-butyldimethylsilylthioether was found suitable to allow subsequent regeneration of the mercapto group after boration. The parent compound, 4-mercaptophenylboronic acid, could thus be obtained and was subsequently S-alkylated; 4-boronophenylthioacetic acid was prepared without the need to protect the boronic acid group. (C) 1999 Elsevier Science S.A. All rights reserved.