2-(3-cyclopentylpropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

• 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-(3-cyclopentylpropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 2-(3-Cyclopentylpropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 化学式: C₁₄H₂₇BO₂
• mdl: MFCD12546194
• 分子量: 238.178
• InChiKey: ADJQPAJSVVAGBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• 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

• 作为产物：
  描述：

  联硼酸频那醇酯 在 (tBuPNN)CoCl2 、 联硼酸频那醇酯 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 25.0 ℃ 、1.5 MPa 条件下， 反应 11.0h， 生成 2-(3-cyclopentylpropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  A highly efficient cobalt-catalyzed deuterogenolysis of diboron: Synthesis of deuterated pinacolborane and vinylboronates

  摘要：

  Highly efficient hydrogenolysis and deuterogenolysis of diboron compounds have been realized by the use of a cobalt catalyst, affording TON up to 48201. Furthermore, a one-pot two-step procedure comprising sequential deuterogenolysis of diboron and deuteroboration of alkynes under the same cobalt catalyst has been developed for the efficient, atom-economical synthesis of deuterated vinylboronates with high deuterium incorporation and excellent regio- and stereoselectivity. (C) 2019 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2019.03.053

文献信息

• Ruthenium-Catalyzed Anti-Markovnikov Selective Hydroboration of Olefins
  作者：Sesha Kisan、Varadhan Krishnakumar、Chidambaram Gunanathan

  DOI：10.1021/acscatal.7b01750

  日期：2017.9.1

  Ruthenium-catalyzed selective hydroboration of styrenes and aliphatic olefins with pinacolborane (HBpin) is reported. This efficient transformation provided products with exclusive anti-Markovnikov selectivity, and this hydroboration protocol is compatible with olefins having electronic and steric divergence as well as diverse functional groups. Hydroboration occurred at room temperature under solvent-free

  据报道，钌与频哪醇硼烷（HBpin）催化苯乙烯和脂族烯烃选择性加氢硼化。这种高效的转化为产物提供了独特的抗马尔科夫尼科夫选择性，并且该硼氢化反应方案与具有电子和空间发散度以及各种官能团的烯烃兼容。在室温下在无溶剂条件下以最小的催化剂负载量（0.05 mol％）进行硼氢化反应，并提供较高的TON（> 1980；每Ru> 990）。机制研究证实的中间体的参与[（η 6 - p -cymene）的RuCl} 2（μ-H-μ-Cl）的]（2）。提出了包括单核钌中间体的催化循环。观察到的抗马尔科夫尼科夫选择性的原理是由可逆的1,3-氢化物转移导致在烯烃上的区域选择性1,2-插入而提供的。
• Rhodium-Catalyzed Dehydrogenative Borylation of Aliphatic Terminal Alkenes with Pinacolborane
  作者：Masao Morimoto、Tomoya Miura、Masahiro Murakami

  DOI：10.1002/anie.201506328

  日期：2015.10.19

  Aliphatic terminal alkenes react with pinacolborane at ambient temperature to afford dehydrogenative borylation compounds as the major product when iPr‐Foxap is used as the ligand with cationic rhodium(I) in the presence of norbornene, which acts as the sacrificial hydrogen acceptor. The reaction is applied to the one‐pot syntheses of aldehydes and homoallylic alcohols from aliphatic terminal alkenes

  当i Pr-Foxap在降冰片烯的存在下用作阳离子铑（I）的配体时，脂族末端烯烃在室温下与频哪醇硼烷反应，以脱氢硼化化合物为主要产物，后者是牺牲氢受体。该反应适用于由脂肪族末端烯烃单醛合成醛和均烯丙基醇。
• A highly efficient cobalt-catalyzed deuterogenolysis of diboron: Synthesis of deuterated pinacolborane and vinylboronates
  作者：Lin Qiao、Lei Zhang、Guixia Liu、Zheng Huang

  DOI：10.1016/j.tet.2019.03.053

  日期：2019.8

  Highly efficient hydrogenolysis and deuterogenolysis of diboron compounds have been realized by the use of a cobalt catalyst, affording TON up to 48201. Furthermore, a one-pot two-step procedure comprising sequential deuterogenolysis of diboron and deuteroboration of alkynes under the same cobalt catalyst has been developed for the efficient, atom-economical synthesis of deuterated vinylboronates with high deuterium incorporation and excellent regio- and stereoselectivity. (C) 2019 Elsevier Ltd. All rights reserved.