4-(triisopropylsilyloxymethyl)benzoic acid

• 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-(triisopropylsilyloxymethyl)benzoic acid
• 英文别名: 4-Triisopropylsilanyloxymethyl-benzoic acid；4-[tri(propan-2-yl)silyloxymethyl]benzoic acid
• 化学式: C₁₇H₂₈O₃Si
• 分子量: 308.493
• InChiKey: WFGGIKXQFJEULV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.08
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(triisopropylsilyloxymethyl)benzoic acid 在 (F)TBAF 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 4-羟甲基苯甲酸
  参考文献：
  名称：

  Fluorous TBAF: A Convenient and Selective Reagent for Fluoride-Mediated Deprotections

  摘要：

  A fluorous analogue of TBAF has been developed for its use in the clean removal of silicon-derived protecting groups. Purification of the crude mixtures by fluorous solid-phase extractions allowed alcohols, amines, and carboxylic acids to be obtained in high purity, with no need of chromatographic separations. The moderate reactivity of fluorous TBAF was exploited in selective deprotections of several bifunctional molecules.

  DOI：

  10.1021/jo901245m
• 作为产物：
  描述：

  4-((triisopropylsilyloxy)methyl)benzaldehyde 在 sodium chlorite 、 双氧水 作用下， 以 乙腈 为溶剂， 以380 mg的产率得到4-(triisopropylsilyloxymethyl)benzoic acid
  参考文献：
  名称：

  Fluorous TBAF: A Convenient and Selective Reagent for Fluoride-Mediated Deprotections

  摘要：

  A fluorous analogue of TBAF has been developed for its use in the clean removal of silicon-derived protecting groups. Purification of the crude mixtures by fluorous solid-phase extractions allowed alcohols, amines, and carboxylic acids to be obtained in high purity, with no need of chromatographic separations. The moderate reactivity of fluorous TBAF was exploited in selective deprotections of several bifunctional molecules.

  DOI：

  10.1021/jo901245m

文献信息

• Mild deprotection of 2-(trimethylsilyl)ethyl esters
  作者：Michael H Serrano-Wu、Alicia Regueiro-Ren、Denis R St. Laurent、Tina M Carroll、Balu N Balasubramanian

  DOI：10.1016/s0040-4039(01)01859-7

  日期：2001.12

  A method for the deprotection of 2-(trimethylsilyl)ethyl (TMSE) esters is described. Treatment of carboxylic esters with NaH in DMF cleanly produces the deprotected acid after extractive work-up. This method can be applied to sterically-hindered substrates as well as esters containing fluoride-labile functionality. A tandem alkylation/ester deprotection procedure is also presented.

  描述了使2-（三甲基甲硅烷基）乙基（TMSE）酯脱保护的方法。在萃取后，用NaH在DMF中处理羧酸酯可干净地产生脱保护的酸。该方法可应用于空间受阻的底物以及含氟不稳定官能团的酯。还提出了串联烷基化/酯脱保护的方法。
• Heteroaromatic quinoline compounds
  申请人：Verhoest R. Patrick

  公开号：US20060154931A1

  公开（公告）日：2006-07-13

  The invention pertains to heteroaromatic compounds that serve as effective phosphodiesterase (PDE) inhibitors. In particular, the invention relates to said compounds which are selective inhibitors of PDE10. The invention also relates to intermediates for preparation of said compounds; pharmaceutical compositions comprising said compounds; and the use of said compounds in a method for treating certain central nervous system (CNS) or other disorders.

  本发明涉及杂环芳香化合物，其作为有效的磷酸二酯酶（PDE）抑制剂。具体而言，本发明涉及选择性抑制PDE10的该类化合物。本发明还涉及用于制备该类化合物的中间体；包含该类化合物的药物组合物；以及使用该类化合物治疗某些中枢神经系统（CNS）或其他疾病的方法。
• HETEROAROMATIC QUINOLINE COMPOUNDS
  申请人：Verhoest Patrick R.

  公开号：US20080214607A1

  公开（公告）日：2008-09-04

  The invention pertains to heteroaromatic compounds that serve as effective phosphodiesterase (PDE) inhibitors. In particular, the invention relates to said compounds which are selective inhibitors of PDE10. The invention also relates to intermediates for preparation of said compounds; pharmaceutical compositions comprising said compounds; and the use of said compounds in a method for treating certain central nervous system (CNS) or other disorders.

  该发明涉及异杂芳烃化合物，其作为有效的磷酸二酯酶（PDE）抑制剂。特别地，该发明涉及选择性抑制PDE10的该类化合物。该发明还涉及用于制备该类化合物的中间体；含有该类化合物的药物组合物；以及使用该类化合物治疗某些中枢神经系统（CNS）或其他疾病的方法。
• Fluorous TBAF: A Convenient and Selective Reagent for Fluoride-Mediated Deprotections
  作者：Santos Fustero、Amador García Sancho、José Luis Aceña、Juan F. Sanz-Cervera

  DOI：10.1021/jo901245m

  日期：2009.8.21

  A fluorous analogue of TBAF has been developed for its use in the clean removal of silicon-derived protecting groups. Purification of the crude mixtures by fluorous solid-phase extractions allowed alcohols, amines, and carboxylic acids to be obtained in high purity, with no need of chromatographic separations. The moderate reactivity of fluorous TBAF was exploited in selective deprotections of several bifunctional molecules.