benzyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanoate

• 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-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanoate
• 英文别名: benzyl (3R)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanoate
• 化学式: C₁₇H₂₅BO₄
• 分子量: 304.194
• InChiKey: NIFUZFAIUNUADF-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 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-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanoate 在 NaBO₃(H₂O)₄ 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 生成 (R)-3-hydroxybutanoic benzyl ester
  参考文献：
  名称：

  手性铑-双恶唑啉基苯基催化剂促进了α，β-不饱和羰基化合物的不对称β-硼酸酯化。

  摘要：

  手性铑-二恶唑啉基苯基乙酸络合物在叔丁醇钠存在下对α，β-不饱和羰基化合物与双（频哪醇）二硼的β-硼酸酯化表现出高催化活性，对映选择性高达97％。

  DOI：

  10.1039/b915759j
• 作为产物：
  描述：

  benzyl (E)-2-butenoate 、 联硼酸频那醇酯 在 [rhodium(III)(bis(COCH₂CH(s-Bu)N)phenyl)(OAc)2(H₂O)] NaOt-Bu 作用下， 以 甲苯 为溶剂， 以87%的产率得到benzyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanoate
  参考文献：
  名称：

  手性铑-双恶唑啉基苯基催化剂促进了α，β-不饱和羰基化合物的不对称β-硼酸酯化。

  摘要：

  手性铑-二恶唑啉基苯基乙酸络合物在叔丁醇钠存在下对α，β-不饱和羰基化合物与双（频哪醇）二硼的β-硼酸酯化表现出高催化活性，对映选择性高达97％。

  DOI：

  10.1039/b915759j

文献信息

• 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。
• 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。

• Exploiting the enantioselectivity of Baeyer-Villiger monooxygenases via boron oxidation
  作者：Patrícia B. Brondani、Hanna Dudek、Joel S. Reis、Marco W. Fraaije、Leandro H. Andrade

  DOI：10.1016/j.tetasy.2012.05.004

  日期：2012.5

  The enantioselective carbon-boron bond oxidation of several chiral boron-containing compounds by Baeyer-Villiger monooxygenases was evaluated. PAMO and M446G PAMO conveniently oxidized 1-phenylethyl boronate into the corresponding 1-(phenyl)ethanol (ee = 82-91%). Cyclopropyl boronic esters were also oxidized but with no enantioselectivity. beta-Boryl carboxylic esters were not oxidized by any BVMOs. (C) 2012 Elsevier Ltd. All rights reserved.
• Asymmetric β-boration of α,β-unsaturated carbonyl compounds with chiral Rh[bis(oxazolinyl)phenyl] catalysts
  作者：Kenji Toribatake、Li Zhou、Ayae Tsuruta、Hisao Nishiyama

  DOI：10.1016/j.tet.2013.02.086

  日期：2013.4

  Chiral rhodium[bis(oxazolinyl)phenyl] complexes exhibited high catalytic activity for the beta-boration of alpha,beta-unsaturated esters, ketones, and amides with bis(pinacolato)diboron in the presence of sodium tertbutoxide to attain high enantioselectivity of up to 97%. The substrate scope and catalytic mechanism were discussed. (C) 2013 Elsevier Ltd. All rights reserved.
• Asymmetric β-boration of α,β-unsaturated carbonyl compounds promoted by chiral rhodium–bisoxazolinylphenyl catalysts
  作者：Takushi Shiomi、Takahiro Adachi、Kenji Toribatake、Li Zhou、Hisao Nishiyama

  DOI：10.1039/b915759j

  日期：——

  Chiral rhodium-bisoxazolinylphenyl acetate complexes exhibited high catalytic activity for the beta-boration of alpha,beta-unsaturated carbonyl compounds with bis(pinacolato)diboron in the presence of sodium t-butoxide with enantioselectivity up to 97%.

  手性铑-二恶唑啉基苯基乙酸络合物在叔丁醇钠存在下对α，β-不饱和羰基化合物与双（频哪醇）二硼的β-硼酸酯化表现出高催化活性，对映选择性高达97％。