benzyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate | 1290145-50-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate
• CAS: 1290145-50-4
• 化学式: C₂₂H₂₇BO₄
• 分子量: 366.265
• InChiKey: RMHACWXHUDNATL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate 、 二乙醇胺 以 乙醚 为溶剂， 反应 0.5h， 以84%的产率得到8-(3-oxo-3-benzyloxy-1-phenylpropyl)hexahydro-1,3,2-oxazaborolo[2,3-b]-1,3,2-oxazaborol-4-ium-8-uide
  参考文献：
  名称：

  A Method for the Deprotection of Alkylpinacolyl Boronate Esters

  摘要：

  A two-step procedure for deprotection of alkylpinacolyl boronate esters via transesterification with diethanolamine followed by hydrolysis was successfully developed with the advantages of tolerance to various functional groups, short reaction time, and ease of product isolation.

  DOI：

  10.1021/jo200250y
• 作为产物：
  描述：

  频哪醇 、 8-(3-oxo-3-benzyloxy-1-phenylpropyl)hexahydro-1,3,2-oxazaborolo[2,3-b]-1,3,2-oxazaborol-4-ium-8-uide 在 盐酸 作用下， 以 正己烷 、 水 为溶剂， 以90%的产率得到benzyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate
  参考文献：
  名称：

  A Method for the Deprotection of Alkylpinacolyl Boronate Esters

  摘要：

  A two-step procedure for deprotection of alkylpinacolyl boronate esters via transesterification with diethanolamine followed by hydrolysis was successfully developed with the advantages of tolerance to various functional groups, short reaction time, and ease of product isolation.

  DOI：

  10.1021/jo200250y

文献信息

• Catalyst-free chemoselective conjugate addition and reduction of α,β-unsaturated carbonyl compounds <i>via</i> a controllable boration/protodeboronation cascade pathway
  作者：Xi Huang、Junjie Hu、Mengying Wu、Jiayi Wang、Yanqing Peng、Gonghua Song

  DOI：10.1039/c7gc02863f

  日期：——

  addition and 1,4-reduction of α,β-unsaturated carbonyl compounds. Without any metal-catalyst or base, a series of β-boration products of α,β-unsaturated carbonyl compounds was easily obtained in moderate to excellent yields in a mixed solvent of ethanol and water. The presence of a catalytic amount of Cs2CO3 can effectively induce further protodeboronation reaction towards 1,4-reduction products at

  已开发出一种新颖，有效的无过渡金属且可控制的硼酸化/原硼酸脱硼策略，用于化学选择性结合物的添加和α，β-不饱和羰基化合物的1,4-还原。在没有任何金属催化剂或碱的情况下，在乙醇和水的混合溶剂中，很容易以中等至极好的收率获得一系列α，β-不饱和羰基化合物的β-硼酸酯产物。催化量的Cs 2 CO 3的存在可以在较高的反应温度下有效地引发进一步的原硼酸脱硼反应，生成1,4-还原产物。因此，通过稍微改变反应条件，可控制地获得α，β-不饱和羰基化合物的硼酸化或还原产物。机理研究表明Cs 2CO 3在激活原去硼化步骤中起关键作用。这种无过渡金属催化剂且产物可控的方法为高化学选择性制备α，β-不饱和羰基化合物的β-硼酸酯产物和1,4-还原产物提供了有用且环保的工具。
• Configuration Sampling With Five‐Membered Atropisomeric <i>P</i> , <i>N</i> ‐Ligands
  作者：Gaurav Dahiya、Mukesh Pappoppula、Aaron Aponick

  DOI：10.1002/anie.202102642

  日期：2021.9

  systematic variation of atropisomeric C1-symmetric P,N ligands to incrementally change the position of the groups within the chiral pocket without modifying their steric parameters. More specifically, the effects of systematic modification of the nitrogen heterocycle in atropisomeric C1-symmetric stack ligands have been investigated in this study. The versatility and applicability of this approach

  在这里，我们报告了一种对阻转异构体 C 1对称 P,N 配体进行系统变异的策略，以逐步改变手性袋中基团的位置，而不修改它们的空间参数。更具体地，本研究已经研究了阻转异构C 1对称堆叠配体中氮杂环的系统修饰的影响。这种方法的多功能性和适用性已在机械上不同的催化对映选择性转化中得到证明，从而鉴定了用于高度对映选择性合成有机硼烷的 P,N-配体。
• [2.2]Paracyclophane-based carbene–copper catalyst tuned by transannular electronic effects for asymmetric boration
  作者：Jianqiang Chen、Wenzeng Duan、Zhen Chen、Manyuan Ma、Chun Song、Yudao Ma

  DOI：10.1039/c6ra14404g

  日期：——

  of planar chiral carbene–copper complexes based on the [2.2]paracyclophane backbone with a pseudo-ortho substitution pattern have been synthesized and applied to asymmetric β-boration of α,β-unsaturated esters. As a result, transannular electronic effects of the substituent of the chiral catalyst have significant influence on the catalytic performance. A variety of chiral β-hydroxyl esters were obtained

  合成了一系列基于[2.2]对环环烷骨架并具有拟邻取代基的平面手性卡宾-铜配合物，并将其应用于α，β-不饱和酯的不对称β-硼酸酯化反应。结果，手性催化剂的取代基的跨环电子效应对催化性能具有显着影响。以优异的对映选择性（高达97％ee）和产率（高达99％）获得了各种手性β-羟基酯。
• Tuning StackPhim Ligands: Applications in Enantioselective Borylation and Alkynylation
  作者：Aaron Aponick、Gaurav Dahiya、Khalil A. Abboud

  DOI：10.1055/a-1730-2473

  日期：2022.5

  Here we present a new stack ligand with a modified imidazoline backbone prepared from cyclohexanediamine. This new stack ligand­, Cy-StackPhim, has been found to complement the parent StackPhim ligand in an enantioselective borylation reaction. Additionally, a correlation between the nature of substituents on the imidazoline ring and the substituents on the electrophile is also discussed.

  在这里，我们介绍了一种新的堆叠配体，它是由环己二胺制备的改性咪唑啉骨架。这种新的堆叠配体Cy-StackPhim已被发现在对映选择性硼化反应中与母体StackPhim配体相互补充。此外，还讨论了咪唑啉环上取代基的性质与电荷亲和性取代基的性质之间的相关性。