benzylboronic acid diisopropyl ester | 162213-35-6

• 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: benzylboronic acid diisopropyl ester
• 英文别名: diisopropyl benzylboronate；Benzyl-di(propan-2-yloxy)borane
• CAS: 162213-35-6
• 化学式: C₁₃H₂₁BO₂
• 分子量: 220.12
• InChiKey: UXIIKKHLGFKFKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  228.9±19.0 °C(Predicted)
• 密度：
  0.916±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  benzylboronic acid diisopropyl ester 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 生成 2-(1-chloro-2-phenylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  P1 Phenethyl peptide boronic acid inhibitors of HCV NS3 protease

  摘要：

  A series of peptide boronic acids containing extended, hydrophobic P1 residues was prepared to probe the shallow, hydrophobic S1 region of HCV NS3 protease. The p-trifluoromethylphenethyl P1 substituent was identified as optimal with respect to inhibitor potency for NS3 and selectivity against elastase and chymotrypsin. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00682-0
• 作为产物：
  描述：

  硼酸三异丙酯 、 苄基溴化镁 以 乙醚 为溶剂， 生成 benzylboronic acid diisopropyl ester
  参考文献：
  名称：

  P1 Phenethyl peptide boronic acid inhibitors of HCV NS3 protease

  摘要：

  A series of peptide boronic acids containing extended, hydrophobic P1 residues was prepared to probe the shallow, hydrophobic S1 region of HCV NS3 protease. The p-trifluoromethylphenethyl P1 substituent was identified as optimal with respect to inhibitor potency for NS3 and selectivity against elastase and chymotrypsin. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00682-0

文献信息

• Synthesis of benzylcyanoborane adducts of amines and separation of their enantiomers; SN2 substitution at boron atom
  作者：Laurent Charoy、Alain Valleix、Thierry Le Gall、Paul Pham van Chuong、Charles Mioskowski、Loïc Toupet

  DOI：10.1039/b006265k

  日期：——

  Benzylcyanoborane adducts of several amines were prepared in four steps from toluene, their enantiomers were separated using chiral phase HPLC and an SN2 pathway was evidenced in the reaction of a trimethylamine-derived enantiomer with pyridine.

  几种胺的苄醇氰硼烷加合物的制备从甲苯开始，历经四步完成。其对映体通过手性相高效液相色谱法进行分离，并且在三甲胺衍生的对映体与吡啶的反应中，SN2反应途径得到了证实。
• Boryl-Directed, Ir-Catalyzed C(sp³)–H Borylation of Alkylboronic Acids Leading to Site-Selective Synthesis of Polyborylalkanes
  作者：Takeshi Yamamoto、Aoi Ishibashi、Michinori Suginome

  DOI：10.1021/acs.orglett.9b02112

  日期：2019.8.16

  place at α-, β-, and γ-C–H bonds, giving polyborylated products including di-, tri-, tetra-, and even pentaborylalkanes. α-C–H borylation was generally found to be the preferred reaction of primary alkylboronic acid derivatives, whereas β- or γ-borylation also occurred if β- or γ-C–H bonds were located on the methyl group.

  吡唑基苯胺是在Ir催化的C（sp 3）–H硼酸酯化反应中连接到烷基硼酸硼原子上的临时导向基团。该反应在α-，β-和γ-C–H键处发生，得到多硼酸酯化产物，包括二，三，四，甚至五碳硼烷。通常发现，α-C–H硼酸酯化是伯烷基硼酸衍生物的首选反应，而如果β-或γ-C–H键位于甲基上，则β-或γ-硼酸酯化也会发生。