5-甲基-2-(4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷-2-基)-苯并[b]噻吩 | 1001200-61-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 5-甲基-2-(4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷-2-基)-苯并[b]噻吩
• 英文名称: pinacol 5-methylbenzo[b]thiophen-2-ylboronate
• 英文别名: 4,4,5,5-Tetramethyl-2-(5-methylbenzo[b]thiophen-2-yl)-1,3,2-dioxaborolane；4,4,5,5-tetramethyl-2-(5-methyl-1-benzothiophen-2-yl)-1,3,2-dioxaborolane
• CAS: 1001200-61-8
• 化学式: C₁₅H₁₉BO₂S
• 分子量: 274.192
• InChiKey: BHSBBJIPUAUESF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  5-甲基-2-(4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷-2-基)-苯并[b]噻吩 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 以62%的产率得到2-(5-(bromomethyl)benzo[b]thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Optimizing Cell Permeation of an Antibiotic Resistance Inhibitor for Improved Efficacy

  摘要：

  Benzo[b]thiophene-2-ylboronic acid, 1, is a 27 nM inhibitor of the class C beta-lactamase AmpC and potentiates the activity of beta-lactam antibiotics in bacteria that express this and related enzymes. As is often true, the potency of compound 1 against the enzymes is much attenuated in cell culture against Gram negative bacteria, where the minimum inhibitor concentration of compound 1 is in the mid-micromolar range. Here, we modulated the properties of this lead to enhance its ability to cross the membrane, using a combination of X-ray crystallography, structure-based design, and application of physical models of outer membrane crossing. This strategy led us to derivatives with substantially improved permeability. Also, the greater solubility of these compounds allowed us to measure their efficacy at higher concentrations than with the lead 1, leading to higher maximum potentiation of the antibiotic effect of ceftazidime on resistant bacteria.

  DOI：

  10.1021/jm070643q
• 作为产物：
  描述：

  5-甲基苯并噻吩 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 5-甲基-2-(4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷-2-基)-苯并[b]噻吩
  参考文献：
  名称：

  五元杂环并苯环类化合物及其制备方法和医药用途

  摘要：

  本发明公开一种五元杂环并苯环类化合物及其制备方法和医药用途，涉及结构如式(I)所示的化合物或其立体异构体、互变异构体或其药学上可接受的盐或其溶剂合物或者前药，本发明还提供本发明式I的化合物在用于制备预防或治疗JAK激酶相关疾病药物中的用途。

  公开号：

  CN114075189A

文献信息

• A versatile method for the hydrolysis of gem-dibromomethylarenes bearing carboxylate or boronate group into aldehydes
  作者：John Kallikat Augustine、Y. Arthoba Naik、Ashis Baran Mandal、Nagaraja Chowdappa、Vinuthan B. Praveen

  DOI：10.1016/j.tet.2007.11.030

  日期：2008.1

  Hydrolysis of geni-dibromomethylarenes bearing carboxylate or boronate group to corresponding aldehydes without affecting the ester group was successfully accomplished in high yields by subjecting them to refluxing pyridine. Both aromatic and heteroaromatic substrates gave the corresponding aldehydes in good yields. This method was efficiently adapted for the large scale synthesis of 2d and 2f. (C) 2007 Elsevier Ltd. All rights reserved.
• <i>gem</i>-Dibromomethylarenes:  A Convenient Substitute for Noncommercial Aldehydes in the Knoevenagel−Doebner Reaction for the Synthesis of α<i>,</i>β-Unsaturated Carboxylic Acids
  作者：John Kallikat Augustine、Yanjerappa Arthoba Naik、Ashis Baran Mandal、Nagaraja Chowdappa、Vinuthan B. Praveen

  DOI：10.1021/jo701888m

  日期：2007.12.1

  [Graphics]A facile synthesis of alpha,beta-unsaturated carboxylic acids from gem-dibromomethylarenes is described. gem-Dibromomethylarenes are employed for the first time in the Knoevenagel-Doebner reaction as aldehyde equivalents for the efficient synthesis of alpha,beta-unsaturated carboxylic acids.
• Optimizing Cell Permeation of an Antibiotic Resistance Inhibitor for Improved Efficacy
  作者：Alberto Venturelli、Donatella Tondi、Laura Cancian、Federica Morandi、Giuseppe Cannazza、Bernardetta Segatore、Fabio Prati、Gianfranco Amicosante、Brian K. Shoichet、M. Paola Costi

  DOI：10.1021/jm070643q

  日期：2007.11.1

  Benzo[b]thiophene-2-ylboronic acid, 1, is a 27 nM inhibitor of the class C beta-lactamase AmpC and potentiates the activity of beta-lactam antibiotics in bacteria that express this and related enzymes. As is often true, the potency of compound 1 against the enzymes is much attenuated in cell culture against Gram negative bacteria, where the minimum inhibitor concentration of compound 1 is in the mid-micromolar range. Here, we modulated the properties of this lead to enhance its ability to cross the membrane, using a combination of X-ray crystallography, structure-based design, and application of physical models of outer membrane crossing. This strategy led us to derivatives with substantially improved permeability. Also, the greater solubility of these compounds allowed us to measure their efficacy at higher concentrations than with the lead 1, leading to higher maximum potentiation of the antibiotic effect of ceftazidime on resistant bacteria.