pinacol (E)-(5-iodo-1-pentenyl)boronate | 141091-29-4

• 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: pinacol (E)-(5-iodo-1-pentenyl)boronate
• 英文别名: (E)-pinacol(5-iodo-1-pentenyl)boronate；2-[(E)-5-iodopent-1-enyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 141091-29-4
• 化学式: C₁₁H₂₀BIO₂
• 分子量: 321.994
• InChiKey: ACABAJZPEYVGJP-SOFGYWHQSA-N

物化性质

• 沸点：
  262.4±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  pinacol (E)-(5-iodo-1-pentenyl)boronate 、 ethyl 4-oxo-4-(pyridin-2-ylthio)butanoate 在 氯化镍二甲氧基乙烷 、 4,4'-二叔丁基-2,2'-二吡啶 、 锌 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 36.0h， 以58%的产率得到ethyl (E)-4-oxo-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)non-8-enoate
  参考文献：
  名称：

  从羧酸衍生物和烷基卤化物合成官能化二烷基酮

  摘要：

  不对称二烷基酮可以通过羧酸氯化物或（2-吡啶基）硫酯与烷基碘或苄基氯化物的镍催化还原偶联直接制备。这个过程可以容忍各种各样的官能团，包括常见的氮保护基团和 C-B 键。甚至可以形成侧接有三级和二级中心的受阻酮。提出的机制涉及(L)Ni(烷基) 2中间体与羧酸衍生物的反应。

  DOI：

  10.1021/ol300217x
• 作为产物：
  描述：

  频哪醇 、 5-碘-1-戊炔 、 dimethyl sulfide borane 以 二氯甲烷 为溶剂， 生成 pinacol (E)-(5-iodo-1-pentenyl)boronate
  参考文献：
  名称：

  Preparation of polyfunctional olefins and allenes using 1,1-bimetallics of zinc and zirconium

  摘要：

  The hydrozirconation of various alkenylzinc halides with Cp2Zr(H)Cl in dry dichloromethane provides 1,1-dimetalloalkanes of zinc and zirconium which react with aldehydes, providing (E)-alkenes with good to excellent stereoselectivity (up to 98% E). The reaction tolerates the presence of a wide range of functionalities in the dimetallic species as well as in the aldehyde, allowing the preparation of functionalized olefins. Ketones can also be olefinated by these reagents. However, only a moderate stereoselectivity is observed. The hydrozirconation of alkynylzinc halides with CP2Zr(H)Cl gives 1,1-dimetalloalkenes of zinc and zirconium which react with aldehydes, affording allenes. The olefination of alpha,beta-unsaturated aldehydes provides a short access of 1,2,4-trienes.

  DOI：

  10.1021/om00013a020

文献信息

• Synthesis of Functionalized Dialkyl Ketones from Carboxylic Acid Derivatives and Alkyl Halides
  作者：Alexander C. Wotal、Daniel J. Weix

  DOI：10.1021/ol300217x

  日期：2012.3.16

  Unsymmetrical dialkyl ketones can be directly prepared by the nickel-catalyzed reductive coupling of carboxylic acid chlorides or (2-pyridyl)thioesters with alkyl iodides or benzylic chlorides. A wide variety of functional groups are tolerated by this process, including common nitrogen protecting groups and C–B bonds. Even hindered ketones flanked by tertiary and secondary centers can be formed. The

  不对称二烷基酮可以通过羧酸氯化物或（2-吡啶基）硫酯与烷基碘或苄基氯化物的镍催化还原偶联直接制备。这个过程可以容忍各种各样的官能团，包括常见的氮保护基团和 C-B 键。甚至可以形成侧接有三级和二级中心的受阻酮。提出的机制涉及(L)Ni(烷基) 2中间体与羧酸衍生物的反应。
• Preparation of polyfunctional olefins and allenes using 1,1-bimetallics of zinc and zirconium
  作者：Charles E. Tucker、Bjoern Greve、Wolfram Klein、Paul Knochel

  DOI：10.1021/om00013a020

  日期：1994.1

  The hydrozirconation of various alkenylzinc halides with Cp2Zr(H)Cl in dry dichloromethane provides 1,1-dimetalloalkanes of zinc and zirconium which react with aldehydes, providing (E)-alkenes with good to excellent stereoselectivity (up to 98% E). The reaction tolerates the presence of a wide range of functionalities in the dimetallic species as well as in the aldehyde, allowing the preparation of functionalized olefins. Ketones can also be olefinated by these reagents. However, only a moderate stereoselectivity is observed. The hydrozirconation of alkynylzinc halides with CP2Zr(H)Cl gives 1,1-dimetalloalkenes of zinc and zirconium which react with aldehydes, affording allenes. The olefination of alpha,beta-unsaturated aldehydes provides a short access of 1,2,4-trienes.