3-ethyl-3-hydroxy-2-methylpentanenitrile | 96790-94-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-ethyl-3-hydroxy-2-methylpentanenitrile
• 英文别名: Pentanenitrile, 3-ethyl-3-hydroxy-2-methyl-
• CAS: 96790-94-2
• 化学式: C₈H₁₅NO
• 分子量: 141.213
• InChiKey: MIKIMPQQGFWAIH-UHFFFAOYSA-N

物化性质

• 沸点：
  256.5±13.0 °C(Predicted)
• 密度：
  0.929±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氯丙腈 、 3-戊酮 在 锰 、 (2,2'-bipyridine)nickel(II) dibromide 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以62%的产率得到3-ethyl-3-hydroxy-2-methylpentanenitrile
  参考文献：
  名称：

  Ni催化的α-氯酸酯的活化：合成α-芳基酯和β-羟基酯的简单方法

  摘要：

  使用镍催化剂，α-氯酸酯与芳基卤化物（α-芳基化）或羰基化合物（Reformatsky）的偶联反应可以在温和的条件下制备各种官能化的芳基丙酸衍生物或β-羟基酯。在芳基丙酸衍生物的合成中，该方法对于带有带吸电子基团或给电子基团的芳基卤化物是有效的。

  DOI：

  10.1016/j.tet.2006.11.055

文献信息

• Iron-Catalysed Reformatsky-Type Reactions
  作者：Muriel Durandetti、Jacques Périchon

  DOI：10.1055/s-2006-926432

  日期：2006.5

  A Reformatsky-type reaction has been developed using iron catalysis in acetonitrile or DMF. Reduction of iron(II) bromide by manganese metal in acetonitrile provides a low-valent iron catalyst, which is the active species; under these conditions, α-chloroesters or nitriles can both be converted into their corresponding derivatives. The method was applicable to both ketones and aldehydes, resulting in the formation of β-hydroxyesters under mild conditions.

  一种 Reformatsky 型反应已采用铁催化体系在乙腈或二甲基甲酰胺中得到开发。通过在乙腈中用锰金属还原二溴化铁，可得到低价铁催化剂，该催化剂为活性物种；在这些条件下，α-氯酯或腈均可转化为相应的衍生物。该方法适用于酮和醛，在温和条件下形成 β-羟基酯。
• Metal exchange between an electrogenerated organonickel species and zinc halide: application to an electrochemical, nickel-catalyzed Reformatsky reaction
  作者：Annie Conan、Soline Sibille、Jacques Perichon

  DOI：10.1021/jo00006a012

  日期：1991.3

  The mechanism of the electroreductive coupling of alpha-chloro esters or alpha-chloro nitriles with carbonyl compounds by the means of a sacrificial zinc anode and a nickel catalyst was elucidated by electroanalytical techniques. The mechanism involved reduction of a Ni(II) complex to a Ni(0) complex, oxidative addition of the alpha-chloro ester to the Ni(0) complex, and a Zn(II)/Ni(II) exchange, leading to an organozinc Reformatsky reagent. The electrosynthesis of various beta-hydroxy esters, beta-hydroxy nitriles, and 2,3-epoxy esters was successfully achieved under extremely mild conditions.
• Iron-Mediated Electrochemical Reaction of α-Chloroesters with Carbonyl Compounds
  作者：Muriel Durandetti、Clothilde Meignein、Jacques Périchon

  DOI：10.1021/ol0273046

  日期：2003.2.1

  Reformatsky-type reactions have been performed efficiently using an electroassisted iron-complex catalysis. Valuable product such as beta-hydroxyesters, ketones or nitriles are thus prepared with high yields.
• Formation and efficient addition of cerium(III) derivative of acetonitrile to ketones
  作者：Hsing-Jang Liu、Naim H. Al-said

  DOI：10.1016/0040-4039(91)80061-a

  日期：1991.9

  The cerium(III) derivative of acetonitrile undergoes addition with ketones efficiently. It adds effectively to hindered ketones and gives 1,2-adduct exclusively with conjugated enones.
• Ni-catalyzed activation of α-chloroesters: a simple method for the synthesis of α-arylesters and β-hydroxyesters
  作者：Muriel Durandetti、Corinne Gosmini、Jacques Périchon

  DOI：10.1016/j.tet.2006.11.055

  日期：2007.1

  Coupling reactions of α-chloroesters with aryl halides (α-arylation) or carbonyl compounds (Reformatsky) using nickel catalyst allow, under mild conditions, the preparation of various functionalized aryl propionic acid derivatives or β-hydroxyesters. In the synthesis of aryl propionic acid derivatives, the process is efficient with aryl halides bearing either electron-withdrawing or electron-donating

  使用镍催化剂，α-氯酸酯与芳基卤化物（α-芳基化）或羰基化合物（Reformatsky）的偶联反应可以在温和的条件下制备各种官能化的芳基丙酸衍生物或β-羟基酯。在芳基丙酸衍生物的合成中，该方法对于带有带吸电子基团或给电子基团的芳基卤化物是有效的。