(S)-ethyl 3-(4-methoxyphenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate | 1198356-00-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-ethyl 3-(4-methoxyphenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate
• 英文别名: ethyl (3S)-3-(4-methoxyphenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate
• CAS: 1198356-00-1
• 化学式: C₁₈H₂₇BO₅
• 分子量: 334.22
• InChiKey: FJOPOTKRAPUXID-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-ethyl 3-(4-methoxyphenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate 在 NaBO₃(H₂O)₄ 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 生成 ethyl (3S)-3-hydroxy-3-(4-methoxyphenyl)propanoate
  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：

  对甲氧基肉桂酸乙酯 、 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-methoxyphenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)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

• The debut of chiral cyclic (alkyl)(amino)carbenes (CAACs) in enantioselective catalysis
  作者：Delphine Pichon、Michele Soleilhavoup、Jennifer Morvan、Glen P. Junor、Thomas Vives、Christophe Crévisy、Vincent Lavallo、Jean-Marc Campagne、Marc Mauduit、Rodolphe Jazzar、Guy Bertrand

  DOI：10.1039/c9sc02810b

  日期：——

  versions as electron-rich neutral stereodirecting ancillary ligands for enantioselective transformations. Herein we demonstrate that cyclic (alkyl)(amino)carbene (CAAC) ligands can also engage in asymmetric transformations, thereby expanding the toolbox of available chiral carbenes.

  NHC 在过渡金属催化中的普及促进了手性版本的发展，作为对映选择性转化的富电子中性立体定向辅助配体。在此，我们证明环状（烷基）（氨基）卡宾（CAAC）配体也可以参与不对称转化，从而扩展了可用手性卡宾的工具箱。
• 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％。
• 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.