6-Hydroxyhexylboronic acid | 909873-04-7

• 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: 6-Hydroxyhexylboronic acid
• CAS: 909873-04-7
• 化学式: C₆H₁₅BO₃
• mdl: MFCD06212363
• 分子量: 145.994
• InChiKey: QBZRBXFDJQFDPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.52
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Hydroxyhexylboronic acid 在 四丙基高钌酸铵 N-甲基吲哚酮 、 potassium hydrogen bifluoride 、 4 A molecular sieve 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.5h， 生成 tetra-n-butylammonium 5-formylpentyltrifluoroborate
  参考文献：
  名称：

  Oxidation of Hydroxyl-Substituted Organotrifluoroborates

  摘要：

  Potassium- and tetra-n-butylammonium organotrifluoroborates containing hydroxyl groups have been prepared and oxidized using several common oxidants. Aryl-, alkenyl-, and alkyltrifluoroborates containing both primary and secondary hydroxyl groups were oxidized in moderate to excellent yields with complete retention of the trifluoroborate moiety. The utility of these oxidized products was demonstrated in a Suzuki-Miyaura cross-coupling reaction.

  DOI：

  10.1021/ja062974i
• 作为产物：
  描述：

  6-(tetrahydropyran-2-yloxy)hex-1-ene 在 硼烷四氢呋喃络合物 、 2,5-二甲基-2,4-己二烯 、 聚合甲醛 、 水 、 甲醇 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以42%的产率得到6-Hydroxyhexylboronic acid
  参考文献：
  名称：

  Oxidation of Hydroxyl-Substituted Organotrifluoroborates

  摘要：

  Potassium- and tetra-n-butylammonium organotrifluoroborates containing hydroxyl groups have been prepared and oxidized using several common oxidants. Aryl-, alkenyl-, and alkyltrifluoroborates containing both primary and secondary hydroxyl groups were oxidized in moderate to excellent yields with complete retention of the trifluoroborate moiety. The utility of these oxidized products was demonstrated in a Suzuki-Miyaura cross-coupling reaction.

  DOI：

  10.1021/ja062974i

文献信息

• Practical and Modular Construction of C(sp³)-Rich Alkyl Boron Compounds
  作者：Yangyang Yang、Jet Tsien、Ayala Ben David、Jonathan M. E. Hughes、Rohan R. Merchant、Tian Qin

  DOI：10.1021/jacs.0c11964

  日期：2021.1.13

  Alkyl boronic acids and esters play an important role in the synthesis of C(sp3)-rich medicines, agrochemicals, and material chemistry. This work describes a new type of transition-metal-free mediated transformation to enable the construction of C(sp3)-rich and sterically hindered alkyl boron reagents in a practical and modular manner. The broad generality and functional group tolerance of this method

  烷基硼酸和酯在富含 C(sp3) 的药物、农用化学品和材料化学的合成中起着重要作用。这项工作描述了一种新型的无过渡金属介导的转化，能够以实用和模块化的方式构建富含 C(sp3) 和空间位阻的烷基硼试剂。通过各种底物，包括与药物化学相关的支架的合成和后期功能化，对该方法的广泛通用性和官能团耐受性进行了广泛检查。这种以烷基硼酸为关键的方法的战略意义通过烷基硼化合物的各种下游功能化得到证明。这种两步并行交叉偶联方法，类似于正式和灵活的烷基-烷基偶联，
• Oxidation of Hydroxyl-Substituted Organotrifluoroborates
  作者：Gary A. Molander、Daniel E. Petrillo

  DOI：10.1021/ja062974i

  日期：2006.8.1

  Potassium- and tetra-n-butylammonium organotrifluoroborates containing hydroxyl groups have been prepared and oxidized using several common oxidants. Aryl-, alkenyl-, and alkyltrifluoroborates containing both primary and secondary hydroxyl groups were oxidized in moderate to excellent yields with complete retention of the trifluoroborate moiety. The utility of these oxidized products was demonstrated in a Suzuki-Miyaura cross-coupling reaction.