dimethyl 3-bromopropylboronate | 118508-71-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: dimethyl 3-bromopropylboronate
• 英文别名: 3-Bromopropyl(dimethoxy)borane
• CAS: 118508-71-7
• 化学式: C₅H₁₂BBrO₂
• 分子量: 194.864
• InChiKey: DEHLODAPNJWEQU-UHFFFAOYSA-N

物化性质

• 沸点：
  82-84 °C(Press: 20 Torr)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  重氮乙酸乙酯 、 dimethyl 3-bromopropylboronate 在 potassium fluoride 、 (三氟甲基)三甲基硅烷 、 三甲基氯硅烷 、 甲醇 作用下， 以 乙二醇二甲醚 为溶剂， 反应 20.33h， 以9%的产率得到ethyl 5-methoxypentanoate
  参考文献：
  名称：

  Reactions of CF3-substituted boranes with α-diazocarbonyl compounds

  摘要：

  Boranes substituted with a CF3-group can be generated from methyl boronic esters RB(OMe)(2) and Me3SiCF3/KF followed by treatment with Me3SiCl. These boranes are stable only in coordinating solvents, and due to the increased Lewis acidity of boron, react rapidly with alpha-diazocarbonyl compounds to give the products of transfer of the organic group from boron. Alkyl, aryl, vinyl, and alkynyl boronic esters can be used in this reaction. (C) 2011 Elsevier Ltd. All rights reserved,

  DOI：

  10.1016/j.tetlet.2011.07.141
• 作为产物：
  描述：

  甲醇 、 3-溴丙烯 在 三甲基硅烷 、 dimethyl sulfide borane 、 三溴化硼 作用下， 以 正己烷 为溶剂， 反应 2.0h， 以52%的产率得到dimethyl 3-bromopropylboronate
  参考文献：
  名称：

  Reactions of CF3-substituted boranes with α-diazocarbonyl compounds

  摘要：

  Boranes substituted with a CF3-group can be generated from methyl boronic esters RB(OMe)(2) and Me3SiCF3/KF followed by treatment with Me3SiCl. These boranes are stable only in coordinating solvents, and due to the increased Lewis acidity of boron, react rapidly with alpha-diazocarbonyl compounds to give the products of transfer of the organic group from boron. Alkyl, aryl, vinyl, and alkynyl boronic esters can be used in this reaction. (C) 2011 Elsevier Ltd. All rights reserved,

  DOI：

  10.1016/j.tetlet.2011.07.141

文献信息

• CARBONI, B.;VAULTIER, M.;CARRIE, R., TETRAHEDRON LETT., 29,(1988) N 11, 1279-1282
  作者：CARBONI, B.、VAULTIER, M.、CARRIE, R.

  DOI：——

  日期：——
• Reactions of CF3-substituted boranes with α-diazocarbonyl compounds
  作者：Pavel K. Elkin、Vitalij V. Levin、Alexander D. Dilman、Marina I. Struchkova、Pavel A. Belyakov、Dmitry E. Arkhipov、Alexander A. Korlyukov、Vladimir A. Tartakovsky

  DOI：10.1016/j.tetlet.2011.07.141

  日期：2011.10

  Boranes substituted with a CF3-group can be generated from methyl boronic esters RB(OMe)(2) and Me3SiCF3/KF followed by treatment with Me3SiCl. These boranes are stable only in coordinating solvents, and due to the increased Lewis acidity of boron, react rapidly with alpha-diazocarbonyl compounds to give the products of transfer of the organic group from boron. Alkyl, aryl, vinyl, and alkynyl boronic esters can be used in this reaction. (C) 2011 Elsevier Ltd. All rights reserved,