(S)-ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(p-tolyl)propanoate | 1429299-16-0

• 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: (S)-ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(p-tolyl)propanoate
• 英文别名: ethyl (3S)-3-(4-methylphenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate
• CAS: 1429299-16-0
• 化学式: C₁₈H₂₇BO₄
• 分子量: 318.221
• InChiKey: GICVGJFXMBAUJF-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  (S)-ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(p-tolyl)propanoate 在 sodium peroxoborate tetrahydrate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.3h， 生成 (S)-ethyl 3-hydroxy-3-(4-methylphenyl)propanoate
  参考文献：
  名称：

  Asymmetric β-boration of α,β-unsaturated carbonyl compounds with chiral Rh[bis(oxazolinyl)phenyl] catalysts

  摘要：

  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.

  DOI：

  10.1016/j.tet.2013.02.086
• 作为产物：
  描述：

  ethyl (E)-3-(4-methylphenyl)acrylate 、 联硼酸频那醇酯 在 C₂₄H₃₅N₂O₇Rh 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以89%的产率得到(S)-ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(p-tolyl)propanoate
  参考文献：
  名称：

  Asymmetric β-boration of α,β-unsaturated carbonyl compounds with chiral Rh[bis(oxazolinyl)phenyl] catalysts

  摘要：

  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.

  DOI：

  10.1016/j.tet.2013.02.086

文献信息

• Enantioselective 1,1-Arylborylation of Alkenes: Merging Chiral Anion Phase Transfer with Pd Catalysis
  作者：Hosea M. Nelson、Brett D. Williams、Javier Miró、F. Dean Toste

  DOI：10.1021/jacs.5b00344

  日期：2015.3.11

  A palladium-catalyzed three-component coupling of α-olefins, aryldiazonium salts, and bis(pinacolato)diboron affords direct access to chiral benzylic boronic esters. This process is rendered highly enantioselective using an unprecedented example of cooperative chiral anion phase transfer and transition-metal catalysis.

  钯催化的α-烯烃、芳基重氮盐和双（频哪醇）二硼的三组分偶联可直接获得手性苄基硼酸酯。使用协作手性阴离子相转移和过渡金属催化的前所未有的例子，使该过程具有高度的对映选择性。
• Application of Bidentate Oxazoline–Carbene Ligands with Planar and Central Chirality in Asymmetric β-Boration of α,β-Unsaturated Esters
  作者：Zonghong Niu、Jianqiang Chen、Zhen Chen、Manyuan Ma、Chun Song、Yudao Ma

  DOI：10.1021/jo5021135

  日期：2015.1.2

  oxazoline-substituted imidazolium salts based on [2.2]paracyclophane were synthesized and characterized. The new bidentate oxazoline–carbene precursor with planar and central chirality had significant advantage than the bicyclic 1,2,4-triazolium salt derived from [2.2]paracyclophane as a monodentate carbene ligand in Cu(I)-catalyzed asymmetric β-boration of α,β-unsaturated esters, giving the desired products

  合成并表征了一系列基于[2.2]对环环烷的新的恶唑啉取代的咪唑鎓盐。新型的具有平面和中心手性的二齿恶唑啉-卡宾前体比由[2.2]对环环烷作为单齿卡宾配体的双环1,2,4-三唑鎓盐在Cu（I）催化的α的不对称β-硼酸酯上具有明显的优势。 ，β-不饱和酯，以高对映选择性和产率得到所需产物。
• Rh-catalyzed Addition of β-Carbonyl Pinacol Alkylboronates to Aldehydes: Asymmetric Synthesis of γ-Butyrolactones
  作者：Changwan Zhang、Jaesook Yun

  DOI：10.1021/ol401468v

  日期：2013.7.5

  The rhodium-catalyzed 1,2-addition of chiral benzylic secondary alkylboronic esters with a coordinating carbonyl group to aldehydes was demonstrated with high levels of enantiospecificity. Pinacol boronic ester derivatives can be employed directly for the addition in the presence of KHF2 without the use of corresponding trifluoroborate salts where retention of the configuration was observed. Enantiomerically

  铑与手性苄基仲烷基硼酸酯的铑催化1，2-加成反应后，对映体的对映体特异性很高。品那可硼酸酯衍生物可以在KHF 2存在下直接用于加成反应，而无需使用相应的三氟硼酸盐，因为在这种情况下观察到了构型的保留。以良好的产率合成了对映体富集的β，γ-二芳基取代的γ-丁内酯。
• 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.