3-hydroxy-2,2-dimethyl-3-phenylpropanenitrile | 50654-42-7

• 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: 3-hydroxy-2,2-dimethyl-3-phenylpropanenitrile
• 英文别名: 3-hydroxy-2,2-dimethyl-3-phenylproprionitrile；3-hydroxy-2,2-dimethyl-3-phenyl-propionitrile；3-Hydroxy-2,2-dimethyl-3-phenyl-propionitril
• CAS: 50654-42-7
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: KRKKSXYOZJKIQS-UHFFFAOYSA-N

物化性质

• 熔点：
  67-68 °C
• 沸点：
  159-164 °C(Press: 1.5 Torr)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxy-2,2-dimethyl-3-phenylpropanenitrile 在 jones reagent 、 硫酸 作用下， 以 水 、 丙酮 为溶剂， 反应 19.0h， 生成 2,2-dimethyl-3-oxo-3-phenyl-propionic acid amide
  参考文献：
  名称：

  Solvent Dependent Photochemical Reactions of 3-(2-Alkylphenyl)-2,2-dimethyl-3-oxopropanoates and Their Related Compounds

  摘要：

  Photochemical reactions of methyl 3-(o-alkylphenyl)-2,2-dimethyl-3-oxopropanotes in hexane gave only the corresponding benzocyclobutenols. However, when irradiation was carried out in methanol, 3-oxonaphthalenones were produced together with the benzocyclobutenols. The ratio of benzocyclobutenol to naphthalenone depends on the bulkiness of the alkyl group in the ortho position. Intermediary 1,4-diradicals or dienols were efficiently trapped by oxygen to afford the corresponding peroxides and/or oxygenated compounds derived from the peroxides.

  DOI：

  10.1021/jo981433b
• 作为产物：
  描述：

  2-碘苯甲醛 在 palladium diacetate 四丁基氟化铵 、 三乙胺 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.75h， 生成 3-hydroxy-2,2-dimethyl-3-phenylpropanenitrile
  参考文献：
  名称：

  腈的Carpalpallading：通过Pd催化ω-（2-碘芳基）烷腈和相关化合物的环化反应合成苯并酮和环戊烯酮。

  摘要：

  已经开发出一种通过腈的分子内碳弹头化合成2，2-二取代的苯并环酮的有效方法。取代的3-（2-碘芳基）丙烷腈的环化以高收率提供茚满酮。该反应与多种官能团相容。该方法已经扩展到四氢萘酮和环戊烯酮的合成。

  DOI：

  10.1021/jo0262006

文献信息

• Lewis Base-catalyzed Cyanomethylation of Carbonyl Compounds with (Trimethylsilyl)acetonitrile
  作者：Yoshikazu Kawano、Nobuya Kaneko、Teruaki Mukaiyama

  DOI：10.1246/cl.2005.1508

  日期：2005.11

  Catalytic cyanomethylation of various carbonyl compounds with (trimethylsilyl)acetonitrile (TMSCH2CN) in the presence of Lewis bases such as cesium or lithium acetate proceeded smoothly to afford t...

  在路易斯碱如铯或乙酸锂的存在下，各种羰基化合物与（三甲基甲硅烷基）乙腈（TMSCH2CN）的催化氰甲基化反应顺利进行，得到了...
• RhI-catalyzed aldol-type reaction of organonitriles under mild conditions
  作者：Akihiro Goto、Kohei Endo、Yu Ukai、Stephan Irle、Susumu Saito

  DOI：10.1039/b800634b

  日期：——

  An aldol-type reaction of organonitriles with aldehydes was catalyzed by a RhI(OR) species under ambient conditions, and the reaction displayed a broad substrate scope with respect to both organonitrile and aldehyde components.

  在环境条件下，RhI（OR）物种催化了有机腈与醛的醛醇型反应，并且该反应对于有机腈和醛组分均显示出较宽的底物范围。
• Reaction of the Electrogenerated Cyanomethyl Anion with Carbonyl Compounds: A Clean and Safe Synthesis of β-Hydroxynitriles
  作者：Gabriele Bianchi、Marta Feroci、Leucio Rossi

  DOI：10.1002/ejoc.200900527

  日期：2009.8

  The electrogenerated cyanomethyl anion reacts with carbonyl compounds to yield the corresponding β-hydroxynitriles in moderate to high yields. The reported methodology is very clean and safe, avoiding the use of any classical base or catalyst. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  电生成的氰基甲基阴离子与羰基化合物反应，以中等至高产率产生相应的 β-羟基腈。报告的方法非常干净和安全，避免使用任何经典碱或催化剂。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• One-Pot Nitrile Aldolization/Hydration Operation Giving β-Hydroxy Carboxamides
  作者：Akihiro Goto、Hiroshi Naka、Ryoji Noyori、Susumu Saito

  DOI：10.1002/asia.201000921

  日期：2011.7.4

  Rhodium to the rescue: The formal aldol products of carboxamides (CONH2) were obtained by using a RhI(OR) (R=H, Me) catalyst under essentially neutral pH and ambient conditions. This novel aldol strategy is based on the catalytic aldol‐type reaction of nitriles, followed by hydration of the nitrile functionality (R1=aromatic or aliphatic, R2 and R3=H or alkyl; see scheme).

  抢救铑：在基本中性的pH值和环境条件下，使用Rh I（OR）（R = H，Me）催化剂，可得到羧酰胺的正式醇醛缩合产物（CONH 2）。这种新的羟醛策略基于腈的催化羟醛型反应，然后水合腈官能团（R 1 =芳族或脂肪族，R 2和R 3 = H或烷基；参见方案）。
• Synthesis of benzocyclic ketones via palladium-catalyzed cyclization of ω-(2-iodoaryl)alkanenitriles
  作者：Alexandre A. Pletnev、Richard C. Larock

  DOI：10.1016/s0040-4039(02)00247-2

  日期：2002.3

  An efficient procedure for the synthesis of 2,2-disubstituted benzocyclic ketones by intramolecular carbopalladation of nitriles has been developed. The cyclization of substituted 3-(2-iodoaryl)propanenitriles affords indanones in high yields. The reaction is compatible with a wide variety of functional groups. This chemistry has been extended to the synthesis of tetralones, a 9-fluorenone and a cyclopentenone

  已经开发了一种通过腈的分子内碳弹孔法合成2,2-二取代的苯并环酮的有效方法。取代的3-（2-碘芳基）丙腈的环化以高收率提供茚满酮。该反应与多种官能团相容。该化学反应已扩展到四氢萘酮，9-芴酮和环戊烯酮的合成。