4-(5,5-二甲基-1,3,2-二噁硼烷)苯甲酸 | 62729-39-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(5,5-二甲基-1,3,2-二噁硼烷)苯甲酸
• 英文名称: 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoic acid
• CAS: 62729-39-9
• 化学式: C₁₂H₁₅BO₄
• 分子量: 234.06
• InChiKey: IGZPAPRBHZGJHV-UHFFFAOYSA-N

物化性质

• 熔点：
  236 °C
• 沸点：
  391.9±25.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.15
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332

反应信息

• 作为反应物：
  描述：

  4-(5,5-二甲基-1,3,2-二噁硼烷)苯甲酸 在 盐酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 [4-(2-Anthracen-9-yloxyethoxycarbonyl)phenyl]boronic acid
  参考文献：
  名称：

  基于四硫富瓦烯-蒽二元基与硼酸基团的新型糖传感器

  摘要：

  设计并合成了一种基于带有硫代硼酸基团的四硫富瓦烯-蒽二聚体的新型糖类传感器。我们的研究采用四硫富瓦烯（TTF）单元作为糖类传感器中的富电子基团，而不是胺基团，而这种新型传感器可以高选择性地检测果糖。

  DOI：

  10.1021/jo050682e
• 作为产物：
  描述：

  4-碘苯硼酸新戊二醇酯 、 methyldiphenylsilanecarboxylic acid 在 potassium trimethylsilonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 甲苯 为溶剂， 反应 0.33h， 以71%的产率得到4-(5,5-二甲基-1,3,2-二噁硼烷)苯甲酸
  参考文献：
  名称：

  Palladium-Catalyzed Synthesis of Aromatic Carboxylic Acids with Silacarboxylic Acids

  摘要：

  Aryl iodides and bromides were easily converted to their corresponding aromatic carboxylic acids via a Pd-catalyzed carbonylation reaction using silacarboxylic acids as an in situ source of carbon monoxide. The reaction conditions were compatible with a wide range of functional groups, and with the aryl iodides, the carbonylation was complete within minutes. The method was adapted to the double and selective isotope labeling of tamibarotene.

  DOI：

  10.1021/ol4003465

文献信息

• Halogen–magnesium exchange on unprotected aromatic and heteroaromatic carboxylic acids
  作者：Felix Kopp、Stefan Wunderlich、Paul Knochel

  DOI：10.1039/b618923g

  日期：——

  The magnesiation of halogenated aromatic and heteroaromatic carboxylic acids is accomplished by their treatment with MeMgCl in the presence of LiCl and subsequent reaction with i-PrMgCl·LiCl; the resulting double-magnesiated species react with a variety of electrophiles in up to 97% yield.

  卤代芳香族和杂芳香族羧酸的镁化通过将其与MeMgCl在LiCl存在下处理，随后与i-PrMgCl·LiCl反应来完成；所得到的双镁化物种可与多种电亲核试剂反应，产率高达97%。
• Palladium-Catalyzed <i>ipso</i>-Borylation of Aryl Halides Promoted by Lewis Acid-Mediated Electrophilic Activation of Aryl(halo)palladium(II) Complex
  作者：Takashi Niwa、Tadashi Takimoto、Yuki Sakata、Takamitsu Hosoya

  DOI：10.1021/acs.orglett.3c03531

  日期：2023.11.17

  organoborons. This reaction involves base-mediated nucleophilic activation of diboron that enables transmetalation of an aryl(halo)palladium(II) intermediate with a diboron. As an alternative, herein, we have established Lewis acid-mediated conditions for borylating (pseudo)haloarenes that require no external base. The electrophilic activation of the aryl(halo)palladium(II) intermediate via dehalogenation

  钯催化芳基卤化物的原硼化反应，即众所周知的宫浦硼化反应，是有机硼的可靠合成方法之一。该反应涉及二硼的碱介导亲核活化，从而使芳基（卤）钯（II）中间体与二硼发生金属转移。作为替代方案，本文中，我们建立了不需要外部碱的路易斯酸介导的（假）卤代芳烃硼基化条件。芳基（卤代）钯（II）中间体通过路易斯酸性锌络合物脱卤而发生亲电活化，促进了硼基化。
• McCormick,J.E.; McElhinney,R.S., Journal of the Chemical Society. Perkin transactions I, 1976, p. 2533 - 2540
  作者：McCormick,J.E.、McElhinney,R.S.

  DOI：——

  日期：——
• Palladium-Catalyzed Synthesis of Aromatic Carboxylic Acids with Silacarboxylic Acids
  作者：Stig D. Friis、Thomas L. Andersen、Troels Skrydstrup

  DOI：10.1021/ol4003465

  日期：2013.3.15

  Aryl iodides and bromides were easily converted to their corresponding aromatic carboxylic acids via a Pd-catalyzed carbonylation reaction using silacarboxylic acids as an in situ source of carbon monoxide. The reaction conditions were compatible with a wide range of functional groups, and with the aryl iodides, the carbonylation was complete within minutes. The method was adapted to the double and selective isotope labeling of tamibarotene.
• A New Saccharide Sensor Based on a Tetrathiafulvalene−Anthracene Dyad with a Boronic Acid Group
  作者：Zhuo Wang、Deqing Zhang、Daoben Zhu

  DOI：10.1021/jo050682e

  日期：2005.7.1

  A new saccharide sensor based on a tetrathiafulvalene−anthracene dyad with a boronic acid group was designed and synthesized. Our study employed the tetrathiafulvalene (TTF) unit as the electron-rich group in the saccharide sensor instead of an amine group, and this new sensor detects fructose with good selectivity.

  设计并合成了一种基于带有硫代硼酸基团的四硫富瓦烯-蒽二聚体的新型糖类传感器。我们的研究采用四硫富瓦烯（TTF）单元作为糖类传感器中的富电子基团，而不是胺基团，而这种新型传感器可以高选择性地检测果糖。