5-methyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexan-3-one | 1453867-91-8

• 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: 5-methyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexan-3-one
• 英文别名: 5-Methyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexan-3-one
• CAS: 1453867-91-8
• 化学式: C₁₃H₂₅BO₃
• 分子量: 240.151
• InChiKey: NTZASVUFZPGRRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexan-3-one 在 sodium perborate monohydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 以74%的产率得到1-hydroxy-5-methyl-hexan-3-one
  参考文献：
  名称：

  Stereocontrolled Synthesis of 1,3-Diols from Enones: Cooperative Lewis Base-Mediated Intramolecular Carbonyl Hydrosilylations

  摘要：

  A streamlined synthesis of beta-hydroxy ketone substrates has been developed to further investigate a recently discovered cooperative Lewis base-mediated intramolecular carbonyl hydrosilylation reaction. The synthesis features an enone beta-borylation/oxidation sequence that has proven to be quite general and high-yielding. This has allowed for additional investigations into the diastereoselectivity of the hydrosilylation reaction through the preparation of important polyketide fragments.

  DOI：

  10.1021/jo401293a
• 作为产物：
  描述：

  5-甲基己-1-烯-3-酮 、 联硼酸频那醇酯 在 copper(l) chloride 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.17h， 以79%的产率得到5-methyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexan-3-one
  参考文献：
  名称：

  Stereocontrolled Synthesis of 1,3-Diols from Enones: Cooperative Lewis Base-Mediated Intramolecular Carbonyl Hydrosilylations

  摘要：

  A streamlined synthesis of beta-hydroxy ketone substrates has been developed to further investigate a recently discovered cooperative Lewis base-mediated intramolecular carbonyl hydrosilylation reaction. The synthesis features an enone beta-borylation/oxidation sequence that has proven to be quite general and high-yielding. This has allowed for additional investigations into the diastereoselectivity of the hydrosilylation reaction through the preparation of important polyketide fragments.

  DOI：

  10.1021/jo401293a

文献信息

• Terminal C(sp ³ )–H borylation through intermolecular radical sampling
  作者：Miao Wang、Yahao Huang、Peng Hu

  DOI：10.1126/science.adj9258

  日期：2024.2.2

  Hydrogen atom transfer (HAT) processes can overcome the strong bond dissociation energies (BDEs) of inert C(sp 3 )–H bonds and thereby convert feedstock alkanes into value-added fine chemicals. Nevertheless, the high reactivity of HAT reagents, coupled with the small differences among various C(sp 3 )–H bond strengths, renders site-selective transformations of straight-chain alkanes a great challenge

  氢原子转移 (HAT) 过程可以克服惰性 C(sp) 的强键解离能 (BDE) 3 )–H键，从而将原料烷烃转化为高附加值的精细化学品。尽管如此，HAT 试剂的高反应活性，加上各种 C(sp 3 )–H键强度，使得直链烷烃的位点选择性转化成为一个巨大的挑战。在这里，我们提出了一种光催化分子间自由基采样过程，用于铁催化末端 C(sp 3 )–H 键存在于具有小空间位阻的底物中，包括无支链烷烃。机理研究表明，该反应通过可逆的 HAT 过程进行，然后进行碳自由基的选择性硼化。硼-亚砜络合物可能有助于观察到高末端区域选择性。