2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanal | 1302132-94-0

• 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-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanal
• CAS: 1302132-94-0
• 化学式: C₁₀H₁₉BO₃
• 分子量: 198.07
• InChiKey: SDGWTUUILMURLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基丙烯醛 、 4,8-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,6,2-dioxazaborocane 在 copper(l) chloride 、 2,2,2-三氟乙醇 作用下， 以 二氯甲烷 为溶剂， 反应 3.08h， 以30%的产率得到2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanal
  参考文献：
  名称：

  Structure and Reactivity of a Preactivated sp²–sp³ Diboron Reagent: Catalytic Regioselective Boration of α,β-Unsaturated Conjugated Compounds

  摘要：

  A novel sp(2)-sp(3) diboron reagent has been developed for the copper-catalyzed beta-boration of alpha,beta-unsaturated conjugated compounds. The reaction proceeds under mild conditions with various substrates, i.e., alpha,beta-unsaturated esters, ketones, nitriles, ynones, amides, and aldehydes, in the absence of additives such as phosphine and sodium tert-butoxide to provide beta-borylhomoenolates in good to excellent yields. The presence of an sp(3)-hybridized boron center, un-ambigously confirmed by X-ray crystallography, sufficiently activates the unsymmetrical pinacolato diisopropanolaminato diboron (PDIPA diboron, 2) to transfer the sp(2)-hybridized boron moiety chemoselectively. These observations suggest that the activation of one of the boron atoms is an essential step in the Cu-catalyzed beta-boration catalytic cycle.

  DOI：

  10.1021/jo2003488

文献信息

• β-Borylation of conjugated carbonyl compounds with silylborane or bis(pinacolato)diboron catalyzed by Au nanoparticles
  作者：Marios Kidonakis、Michael Fragkiadakis、Manolis Stratakis

  DOI：10.1039/d0ob01806f

  日期：——

  Conjugated aldehydes and ketones undergo reaction with Me2PhSiBpin (pin: pinacolato) catalyzed by Au nanoparticles supported on TiO2 forming exclusively the β-borylation products, via the intermediate formation of the labile silaboration adducts. This chemoselectivity pathway is complementary to the so far known analogous reaction catalyzed by other metals, where β-silylation occurs instead. β-Borylation

  共轭醛和酮与Me 2 PhSiBpin（pin：pinacolato）发生反应，这是通过不稳定形成的硅烷化加合物的中间形成，而Au纳米颗粒负载在TiO 2上，仅形成β-硼化产物。这种化学选择性途径是迄今为止由其他金属催化的类似反应的补充，在其他类似反应中发生了β-甲硅烷基化。在相同的反应条件下，在各种共轭羰基化合物中，pinBBpin也会发生β-硼化反应，这些共轭羰基化合物包括在其尝试的Au催化的合成中没有反应性的酯和酰胺。