2,2-dimethyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-1-ol

• 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: 2,2-dimethyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-1-ol
• 英文别名: α-hydroxyneopentyl(pinacol)boronate；(tret-butyl)CH(OH)B(2,3-dimethyl-2,3-butanediolate)；(tret-butyl)CH(OH)B(pinacolate)；2,2-Dimethyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-1-ol
• 化学式: C₁₁H₂₃BO₃
• 分子量: 214.113
• InChiKey: QPGKUHIWUPBIRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-1-ol 在 potassium hydride 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 potassium (1-benzyloxy-2,2-dimethylpropyl)trifluoroboranuide
  参考文献：
  名称：

  二级有机三氟硼酸盐的立体有择交叉偶联：1-（苄氧基）烷基三氟硼酸钾

  摘要：

  1-(烷氧基/酰氧基)烷基三氟硼酸钾是通过铜催化的醛二硼化反应和随后得到的1-(羟基)烷基三氟硼酸钾的转化合成的。钯催化的 Suzuki-Miyaura 反应使用 1-（苄氧基）烷基三氟硼酸钾与芳基和杂芳基氯化物，以高产率获得受保护的仲醇。通过使用苄基保护基团避免了 β-氢化物消除途径，建议通过芳烃与金属中心的配位来稳定二有机钯中间体。这种交叉偶联是立体有择的，完全保留了立体化学。

  DOI：

  10.1021/ja307861n
• 作为产物：
  描述：

  联硼酸频那醇酯 在 ICyCuCl 、 silica gel 、 sodium t-butanolate 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 2.0h， 生成 2,2-dimethyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-1-ol
  参考文献：
  名称：

  Facile Formation of β-Hydroxyboronate Esters by a Cu-Catalyzed Diboration/Matteson Homologation Sequence

  摘要：

  The copper-catalyzed diboration of aldehydes was used in conjunction with the Matteson homologation, providing the efficient synthesis of beta-hydroxyboronate esters. The oxygen-bound boronate ester was found to play a key role in mediating the homologation reaction, which was compared to the a-hydroxyboronate ester (isolated hydrolysis product). The synthetic utility of the diboration/homologation sequence was demonstrated through the oxidation of one product to provide a 1,2-diol.

  DOI：

  10.1021/ol502767m

文献信息

• Catalytic Diboration of Aldehydes via Insertion into the Copper−Boron Bond
  作者：David S. Laitar、Emily Y. Tsui、Joseph P. Sadighi

  DOI：10.1021/ja064019z

  日期：2006.8.1

  Mesitaldehyde reacts cleanly with (IPr)CuB(pin) [IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene); pin = 2,3-dimethyl-2,3-butanediolate] to afford the product complex 1, the first well-defined product of carbonyl group insertion into a metal-boron bond. Analysis of 1 by NMR spectroscopy and single-crystal X-ray diffraction indicates the formation of a copper-carbon and a boron-oxygen bond. A copper(I) precatalyst supported by the less sterically demanding ligand ICy (1,3-dicyclohexylimidazol-2-ylidene) achieves the efficient 1,2-diboration of aryl-, heteroaryl-, and alkyl-substituted aldehydes at room temperature.
• Stereospecific Cross-Coupling of Secondary Organotrifluoroborates: Potassium 1-(Benzyloxy)alkyltrifluoroborates
  作者：Gary A. Molander、Steven R. Wisniewski

  DOI：10.1021/ja307861n

  日期：2012.10.10

  Potassium 1-(alkoxy/acyloxy)alkyltrifluoroborates have been synthesized through a copper-catalyzed diboration of aldehydes and subsequent conversion of the resulting potassium 1-(hydroxy)alkyltrifluoroborates. The palladium-catalyzed Suzuki-Miyaura reaction employing the potassium 1-(benzyloxy)alkyltrifluoroborates with aryl and heteroaryl chlorides provides access to protected secondary alcohols in

  1-(烷氧基/酰氧基)烷基三氟硼酸钾是通过铜催化的醛二硼化反应和随后得到的1-(羟基)烷基三氟硼酸钾的转化合成的。钯催化的 Suzuki-Miyaura 反应使用 1-（苄氧基）烷基三氟硼酸钾与芳基和杂芳基氯化物，以高产率获得受保护的仲醇。通过使用苄基保护基团避免了 β-氢化物消除途径，建议通过芳烃与金属中心的配位来稳定二有机钯中间体。这种交叉偶联是立体有择的，完全保留了立体化学。
• Facile Formation of β-Hydroxyboronate Esters by a Cu-Catalyzed Diboration/Matteson Homologation Sequence
  作者：Cameron M. Moore、Casey R. Medina、Peter C. Cannamela、Melissa L. McIntosh、Carl J. Ferber、Andrew J. Roering、Timothy B. Clark

  DOI：10.1021/ol502767m

  日期：2014.12.5

  The copper-catalyzed diboration of aldehydes was used in conjunction with the Matteson homologation, providing the efficient synthesis of beta-hydroxyboronate esters. The oxygen-bound boronate ester was found to play a key role in mediating the homologation reaction, which was compared to the a-hydroxyboronate ester (isolated hydrolysis product). The synthetic utility of the diboration/homologation sequence was demonstrated through the oxidation of one product to provide a 1,2-diol.

表征谱图