2-(4-ethylphenyl)-5,5-dimethyl-1,3,2-dioxaborinane | 1594124-64-7

• 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: 2-(4-ethylphenyl)-5,5-dimethyl-1,3,2-dioxaborinane
• 英文别名: 2-(4-Ethylphenyl)-5,5-dimethyl-1,3,2-dioxaborinane
• CAS: 1594124-64-7
• 化学式: C₁₃H₁₉BO₂
• 分子量: 218.104
• InChiKey: BIWWTNQHQKKNBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-ethylphenyl)-5,5-dimethyl-1,3,2-dioxaborinane 在 四(三苯基膦)钯 、 potassium carbonate 、 (4S,4′S)-(-)-2,2′-(3-戊烯基)双(4-异丙基噁唑啉) 、 silver(l) oxide 作用下， 以 乙醚 为溶剂， 反应 23.83h， 生成 (S)-1-((4-ethylphenyl)(phenyl)methyl)-3-methoxybenzene
  参考文献：
  名称：

  Synthesis of Enantiomerically Enriched Triarylmethanes by Enantiospecific Suzuki–Miyaura Cross-Coupling Reactions

  摘要：

  The Suzuki-Miyaura cross-coupling of chiral, enantiomerically enriched dibenzylic boronic esters is described. The reaction proceeds with almost complete retention of stereochemistry, providing access to triaryl-methanes, compounds that have high biological activity and are difficult to prepare in enantiomerically pure form using other methods.

  DOI：

  10.1021/ja412159g
• 作为产物：
  描述：

  4-乙基苯硼酸 、 2,2-二甲基-1,3-丙二醇 在 magnesium sulfate 作用下， 以 乙醚 为溶剂， 反应 20.0h， 以100%的产率得到2-(4-ethylphenyl)-5,5-dimethyl-1,3,2-dioxaborinane
  参考文献：
  名称：

  Synthesis of Enantiomerically Enriched Triarylmethanes by Enantiospecific Suzuki–Miyaura Cross-Coupling Reactions

  摘要：

  The Suzuki-Miyaura cross-coupling of chiral, enantiomerically enriched dibenzylic boronic esters is described. The reaction proceeds with almost complete retention of stereochemistry, providing access to triaryl-methanes, compounds that have high biological activity and are difficult to prepare in enantiomerically pure form using other methods.

  DOI：

  10.1021/ja412159g

文献信息

• Ni-Catalyzed Cross-Coupling of Dimethyl Aryl Amines with Arylboronic Esters under Reductive Conditions
  作者：Zhi-Chao Cao、Si-Jun Xie、Huayi Fang、Zhang-Jie Shi

  DOI：10.1021/jacs.8b08779

  日期：2018.10.24

  Herein, we reported a successful Suzuki-Miyaura coupling of dimethyl aryl amines to forge biaryl skeleton via Ni catalysis in the absence of directing groups and preactivation. This transformation proceeded with high efficiency in the presence of magnesium. Preliminary mechanism studies demonstrated dual roles of magnesium: (i) a reductant that reduced Ni(II) species to active Ni(I) catalyst; (ii)

  在此，我们报道了在没有导向基团和预活化的情况下，通过 Ni 催化，二甲基芳胺成功的 Suzuki-Miyaura 偶联形成联芳骨架。这种转变在镁的存在下以高效率进行。初步机理研究证明了镁的双重作用：(i) 将 Ni(II) 物质还原为活性 Ni(I) 催化剂的还原剂；(ii) 促进 Ni(I)/Ni(III) 催化循环的独特促进剂。
• Synthesis of Enantiomerically Enriched Triarylmethanes by Enantiospecific Suzuki–Miyaura Cross-Coupling Reactions
  作者：Smitha C. Matthew、Ben W. Glasspoole、Patrick Eisenberger、Cathleen M. Crudden

  DOI：10.1021/ja412159g

  日期：2014.4.23

  The Suzuki-Miyaura cross-coupling of chiral, enantiomerically enriched dibenzylic boronic esters is described. The reaction proceeds with almost complete retention of stereochemistry, providing access to triaryl-methanes, compounds that have high biological activity and are difficult to prepare in enantiomerically pure form using other methods.