3-hydroxy-3-methyl-5-phenylpent-4-enenitrile | 86503-53-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: 3-hydroxy-3-methyl-5-phenylpent-4-enenitrile
• 英文别名: (E)-3-hydroxy-3-methyl-5-phenylpent-4-enenitrile
• CAS: 86503-53-9
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: QFVFYUVCSFHKHZ-BQYQJAHWSA-N

物化性质

• 沸点：
  393.1±30.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (E)-3-Hydroxy-3-methyl-5-phenyl-2-trimethylsilanyl-pent-4-enenitrile 在 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 3-hydroxy-3-methyl-5-phenylpent-4-enenitrile
  参考文献：
  名称：

  Direct Catalytic Aldol-Type Reactions Using RCH₂CN

  摘要：

  A copper fluoride-catalyzed cyanomethylation that can be applied to a wide range of ketones and aldehydes was developed using TMSCH2-CN as a nucleophile. The reaction was extended to a conceptually more advanced copper alkoxide-catalyzed direct addition of alkylnitriles to aldehydes, which can act as a surrogate direct catalytic aldol reaction of esters. These reactions can be applied to the first catalytic enantioselective cyanomethylation of ketones and direct catalytic enantioselective cyanomethylation of aldehydes.

  DOI：

  10.1021/ol035206u

文献信息

• Catalytic cyanomethylation of carbonyl compounds and imines with highly basic phosphine
  作者：Satoru Matsukawa、Eri Kitazaki

  DOI：10.1016/j.tetlet.2008.02.155

  日期：2008.4

  A highly basic phosphine, tris(2,4,6-trimethoxy phenyl)phosphine (TTMPP), catalyzes cyanomethylation using trimethylsilylacetonitrile (TMSCH2CN) to give the corresponding products in good to high yields, with both carbonyl compounds and imines.

  高碱性膦三（2,4,6-三甲氧基苯基）膦（TTMPP）使用三甲基甲硅烷基乙腈（TMSCH 2 CN）催化氰基甲基化，从而以羰基化合物和亚胺的高收率得到相应的产物。
• Ruthenium-catalyzed formation of pyrazoles or 3-hydroxynitriles from propargyl alcohols and hydrazines
  作者：Julia Kaufmann、Elisabeth Jäckel、Edgar Haak

  DOI：10.24820/ark.5550190.p010.893

  日期：——

  Functionalized pyrazoles are generated from secondary propragyl alcohols and hydrazines in a rutheniumcatalyzed cascade process, consisting of redox isomerization, Michael addition, cyclocondensation and dehydrogenation steps. The same bifunctional catalyst mediates the conversion of tertiary propargyl alcohols with hydrazine to 3-hydroxynitriles via anti-Markovnikov hydroamination followed by elimination

  官能化吡唑是在钌催化的级联过程中由仲丙醇和肼生成的，包括氧化还原异构化、迈克尔加成、环缩合和脱氢步骤。相同的双功能催化剂通过反马尔可夫尼科夫加氢胺化随后消除氨来介导炔丙醇叔醇与肼的转化为 3-羟基腈。
• Reactions with lithium dimethylcuprate and lithium dimethylaurate
  作者：Gerd Hallnemo、Christina Ullenius

  DOI：10.1016/s0040-4020(01)88572-0

  日期：1983.1

  The reaction of lithium dimethylcuprate with E-4-phenyl-3-buten-2-one in different solvents has been investigated. Fast conjugate addition occurs in hydrocarbons, dichloromethane and diethylether, while the reaction is retarded in better coordinating solvents.

  研究了二甲基铜锂锂与E -4-苯基-3-丁烯-2-酮在不同溶剂中的反应。在烃，二氯甲烷和二乙醚中快速共轭加成，而在更好的配位溶剂中反应被延迟。
• Nucleophilic Addition of α-(Dimethylsilyl)nitriles to Aldehydes and Ketones
  作者：Takaaki Jinzaki、Mitsuru Arakawa、Hidenori Kinoshita、Junji Ichikawa、Katsukiyo Miura

  DOI：10.1021/ol401663u

  日期：2013.7.19

  (dimethylsilyl)acetonitriles (Me2HSiCR3R4CN) react spontaneously with aldehydes in DMSO to give β-hydroxynitriles in good to high yields. The addition to ketones is effectively promoted by using MgCl2 or CaCl2. (Dimethylsilyl)acetonitrile (Me2HSiCH2CN) shows lower reactivity than the α-alkylated analogues. However, the parent reagent adds efficiently to aldehydes and ketones under catalysis by AcOLi or MgCl2.

  α-烷基化的（二甲基甲硅烷基）乙腈（Me 2 HSiCR 3 R 4 CN）与醛在DMSO中自发反应，以高至高收率得到β-羟基腈。通过使用MgCl 2或CaCl 2可以有效地促进酮的添加。（二甲基甲硅烷基）乙腈（Me 2 HSiCH 2 CN）显示出比α-烷基化类似物低的反应性。但是，母体试剂在AcOLi或MgCl 2的催化下可以有效地添加到醛和酮中。