2-(4-(Dibromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane | 1006598-62-4

• 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: 2-(4-(Dibromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane
• 英文别名: 2-[4-(dibromomethyl)phenyl]-5,5-dimethyl-1,3,2-dioxaborinane
• CAS: 1006598-62-4
• 化学式: C₁₂H₁₅BBr₂O₂
• 分子量: 361.869
• InChiKey: DLNGFCLTVGSLEE-UHFFFAOYSA-N

物化性质

• 熔点：
  135-137 °C
• 沸点：
  389.9±32.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-(Dibromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane 在 吡啶 、 水 作用下， 反应 1.5h， 以93%的产率得到4-(5,5-二甲基-1,3,2-二氧杂己硼烷-2-基)苯甲醛
  参考文献：
  名称：

  A versatile method for the hydrolysis of gem-dibromomethylarenes bearing carboxylate or boronate group into aldehydes

  摘要：

  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.

  DOI：

  10.1016/j.tet.2007.11.030
• 作为产物：
  描述：

  4-甲基苯硼酸新戊基二醇酯 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87%的产率得到2-(4-(Dibromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane
  参考文献：
  名称：

  A versatile method for the hydrolysis of gem-dibromomethylarenes bearing carboxylate or boronate group into aldehydes

  摘要：

  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.

  DOI：

  10.1016/j.tet.2007.11.030

文献信息

• ¹⁴C-Labeled and Large-Scale Synthesis of the Angiotensin-(1−7)-receptor Agonist AVE 0991 by Cross-Coupling Reactions
  作者：Volker Derdau、Raymond Oekonomopulos、Gerrit Schubert

  DOI：10.1021/jo034372c

  日期：2003.6.1

  The synthesis of C-14-labeled AVE 0991 (C-14-1a) and large-scale synthesis of AVE 0991 (1a) are described. In the key step of the synthesis, the C-C coupling reaction of the imidazole (2) and thiophene (3) building blocks was studied under Suzuki and Stille reaction conditions, respectively. Suzuki reaction gave only moderate yields, whereas the best results were obtained under Stille reaction conditions with up to 64% yield.
• 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.