allenylboronic acid 2,2-dimethyl-1,3-propanediol ester | 57186-58-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: allenylboronic acid 2,2-dimethyl-1,3-propanediol ester
• 英文别名: 2-allenyl-5,5-dimethyl-1,3,2-dioxaborinane
• CAS: 57186-58-0
• 化学式: C₈H₁₃BO₂
• 分子量: 152.001
• InChiKey: XFEHWDQZYKOGQF-UHFFFAOYSA-N

物化性质

• 沸点：
  160.1±23.0 °C(Predicted)
• 密度：
  0.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  二苯甲酮 、 allenylboronic acid 2,2-dimethyl-1,3-propanediol ester 在 bis(bis(trimethylsilyl)amido)zinc(II) 作用下， 以 甲苯 为溶剂， 反应 36.0h， 以92%的产率得到1,1-diphenylbuta-2,3-dien-1-ol
  参考文献：
  名称：

  Zinc Amide Catalyzed Regioselective Allenylation and Propargylation of Ketones with Allenyl Boronate

  摘要：

  Zinc amide catalyzed, regioselective allenylation and propargylation of ketones with allenyl boronate is reported. Tertiary allenyl and homopropargyl alcohols were obtained, respectively, in high selectivities, from the same starting materials, simply by changing the reaction conditions. The substrate scope was wide. Mechanistic studies suggest that the reactions are controlled under kinetic and thermodynamic conditions.

  DOI：

  10.1021/acs.orglett.5b03045
• 作为产物：
  描述：

  allenylmagnesium bromide 、 2,2-二甲基-1,3-丙二醇 在 硼酸三甲酯 、 盐酸 、 magnesium sulfate 作用下， 以 乙醚 、 水 为溶剂， 反应 43.0h， 以69%的产率得到allenylboronic acid 2,2-dimethyl-1,3-propanediol ester
  参考文献：
  名称：

  Development of a double allylboration reagent targeting 1,5-syn-(E)-diols: application to the synthesis of the C(23)–C(40) fragment of tetrafibricin

  摘要：

  Interest in the synthesis of the C(23) C(40) fragment 2 of tetrafibricin prompted us to develop a new method for the synthesis of 1,5-syn-(E)-diols. Toward this end, the kinetically controlled hydroboration of allenes 6, 33, ent-39, 42, and 45 with the Soderquist borane 25R were studied. Tetrabutylammonium allenyltrifluoroborate 45 gave superior results and was utilized in a double allylboration sequence with two different aldehydes to provide the targeted 1,5-syn-(E)-diols in generally high yields (72-98%), and with high enantioselectivity (>95% ee), diastereoselectivity (dr >20:1), and (E)/(Z) selectivity (>20:1). This new method was applied to the synthesis of the C(23) C(40) fragment 2 of tetrafibricin. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.008

文献信息

• Development of a double allylboration reagent targeting 1,5-syn-(E)-diols: application to the synthesis of the C(23)–C(40) fragment of tetrafibricin
  作者：Philippe Nuhant、Jeremy Kister、Ricardo Lira、Achim Sorg、William R. Roush

  DOI：10.1016/j.tet.2011.06.008

  日期：2011.9

  Interest in the synthesis of the C(23) C(40) fragment 2 of tetrafibricin prompted us to develop a new method for the synthesis of 1,5-syn-(E)-diols. Toward this end, the kinetically controlled hydroboration of allenes 6, 33, ent-39, 42, and 45 with the Soderquist borane 25R were studied. Tetrabutylammonium allenyltrifluoroborate 45 gave superior results and was utilized in a double allylboration sequence with two different aldehydes to provide the targeted 1,5-syn-(E)-diols in generally high yields (72-98%), and with high enantioselectivity (>95% ee), diastereoselectivity (dr >20:1), and (E)/(Z) selectivity (>20:1). This new method was applied to the synthesis of the C(23) C(40) fragment 2 of tetrafibricin. (C) 2011 Elsevier Ltd. All rights reserved.
• Zinc Amide Catalyzed Regioselective Allenylation and Propargylation of Ketones with Allenyl Boronate
  作者：Yasuhiro Yamashita、Yi Cui、Peizhong Xie、Shu̅ Kobayashi

  DOI：10.1021/acs.orglett.5b03045

  日期：2015.12.18

  Zinc amide catalyzed, regioselective allenylation and propargylation of ketones with allenyl boronate is reported. Tertiary allenyl and homopropargyl alcohols were obtained, respectively, in high selectivities, from the same starting materials, simply by changing the reaction conditions. The substrate scope was wide. Mechanistic studies suggest that the reactions are controlled under kinetic and thermodynamic conditions.