2-phenylpropanamide | 1125-70-8

• 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: 2-phenylpropanamide
• 英文别名: 2-phenylpropionamide；α-methylphenylacetamide；(+/-)-2-Phenyl-propionsaeure-amid；α-methylbenzylamide
• CAS: 1125-70-8
• 化学式: C₉H₁₁NO
• 分子量: 149.192
• InChiKey: DOZZSWAOPDYVLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存放在室温、密封、干燥处。

反应信息

• 作为反应物：
  描述：

  2-phenylpropanamide 在 Klebsiella oxytoca 38.1.2 amidase 作用下， 生成 2-苯基丙酸
  参考文献：
  名称：

  Enantioselective conversion of α-arylnitriles by Klebsiella oxytoca

  摘要：

  A new bacterial isolate Klebsiella oxytoca 38.1.2 with stereoselective nitrile hydratase activity against rac-2-phenylglycine nitrile, rac-2-phenylpropionitrile and rac-mandelonitrile was investigated. The cultivation conditions for growth and nitrile hydratase formation were studied. An intracellular (S)-enantioselective nitrile hydratase and a putative (S)-selective amidase were found to be induced in the presence of rac-2-phenylpropionitrile. The temperature dependence on the enantioselectivity of the nitrile hydratase active cells was studied in more detail for the biotransformation of rac-2-phenylpropionitrile and rac-mandelonitrile. By increasing the temperature from 15 degrees C to 37 degrees C, the apparent enantiomeric ratio of the conversion of rac-2-phenylpropionitrile to (S)-2-phenylpropionamide increased from 16 to 35 at nearly 50% conversion rate. rac-Mandelonitrile was converted to (S)-mandelamide with an enantiomeric excess of up to 95% in a 80% yield without further conversion to mandelic acid. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2008.11.014
• 作为产物：
  描述：

  2-苯基丙醛 在 羟胺 、 copper diacetate 作用下， 以 水 为溶剂， 反应 48.0h， 以99%的产率得到2-phenylpropanamide
  参考文献：
  名称：

  Copper(II) acetate-catalyzed one-pot conversion of aldehydes into primary amides through a Beckmann-type rearrangement

  摘要：

  Copper(II) acetate is a versatile catalyst for the direct transformation of any type of aldehydes into primary amides by stoichiometric reaction with hydroxylamine in water. The catalyst could be recovered 10 times without losing its activity, just by a simple organic layer extraction of the product. The catalyst and the protocol avoid the use of any type of expensive and difficult to handle organic ligand, as well as bases, showing excellent yields, under mild reaction conditions. The great purity of the crude product permits its purification by a simple recrystallization process. The whole protocol fulfils the principle of green chemistry and sustainability, minimizing the use of organic solvents and any type of wastes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.085

文献信息

• Synthesis of α-Arylcarboxylic Acid Amides from Silyl Enol Ether via Migratory Amidation with 2-Azido-1,3-dimethylimidazolinium Hexafluorophosphate
  作者：Mitsuru Kitamura、Kento Murakami、Yuichiro Shiratake、Tatsuo Okauchi

  DOI：10.1246/cl.130195

  日期：2013.7.5

  α-Arylcarboxylic acid amides were synthesized by reacting silyl enol ethers of aryl ketones and 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP, 1). Silyl enol ethers react with ADMP 1 to give N-(α-arylacyl)guanidines via the migration of aryl groups in enol ethers. The products were transformed to the corresponding α-aryl acetamides by treating with LiAlH4.

  α-芳基羧酰胺通过苯乙酮的硅醚与2-叠氮-1,3-二甲基咪唑六氟磷酸盐（ADMP，1）反应合成。硅醚与ADMP 1反应，通过烯醇醚中的芳基迁移生成N-(α-芳基酰基)胍。产物通过与LiAlH4处理转化为相应的α-芳基乙酰胺。
• 一种含炔基的芳基酰胺类衍生物及其制备方法和应用
  申请人：广东工业大学

  公开号：CN109942616A

  公开（公告）日：2019-06-28

  本发明属于有机合成技术领域，尤其涉及一种含炔基的芳基酰胺类衍生物及其制备方法和应用。本发明提供了一种含炔基的芳基酰胺类衍生物，所述含炔基的芳基酰胺类衍生物的结构式如式(Ⅰ)所示；其中，Ar为芳基，包括芳香杂环基、苯基或芳香稠环基；R1选自氢、卤元素、醚基或含官能团的烃基；R2为氢或烷基；R3为多取代硅基。本发明芳基酰胺类衍生物引入了具有多功能性的炔基，并且炔基在芳基上位于酰胺基的邻位，鉴于炔基的碳碳三键的丰富的化学活性，以及芳基酰胺在药物中的广泛应用，本发明含炔基的芳基酰胺类衍生物在药物开发中具有良好的应用前景。
• <scp>Regio‐Divergent</scp> C—H Alkynylation with Janus Directing Strategy <i>via</i> Ir( <scp>III</scp> ) Catalysis
  作者：Xianwei Li、Guangxin Liang、Zhang‐Jie Shi

  DOI：10.1002/cjoc.202000204

  日期：2020.9

  Directing strategy has been extensively exploited to maintain activity and selectivity for the rapid access to functionalized molecules and pharmaceutical targets. However, ‘one‐to‐one’ activation model was usually achieved through traditional directing strategy. Herein, we achieved ‘one‐to‐two’ activation model by slight modification of simple and practical ketoxime and amide functionality. With judicious

  指导策略已得到广泛利用，以保持活性和选择性，以快速获得功能化分子和药物靶标。但是，“一对一”激活模型通常是通过传统的指导策略来实现的。在这里，我们通过对简单而实用的酮肟和酰胺功能进行一些修改，实现了“一对二”激活模型。通过明智地选择导向基团，实现了Csp 3 -H和Csp 2 -H键的炔基化反应，更重要的是，实现了脱氢的Csp 3 -H炔基化，从而实现了药物在区域上的分散后期修饰。
• One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles
  作者：Jan Otevrel、David Svestka、Pavel Bobal

  DOI：10.1039/d0ra04359a

  日期：——

  We have identified a novel one-pot method for the synthesis of β-amino alcohols, which is based on C–H bond hydroxylation at the benzylic α-carbon atom with a subsequent nitrile or amide functional group reduction. This cascade process uses molecular oxygen as an oxidant and sodium bis(2-methoxyethoxy)aluminum hydride as a reductant. The substrate scope was examined on 30 entries and, although the

  我们已经确定了一种用于合成 β-氨基醇的新型一锅法，该方法基于苄基 α-碳原子上的 C-H 键羟基化，随后腈或酰胺官能团还原。这种级联过程使用分子氧作为氧化剂和双（2-甲氧基乙氧基）氢化铝钠作为还原剂。对 30 个条目检查了底物范围，尽管相应产品仅以中等产率提供，但上述简单方案可作为其他难以制备的空间拥挤 1,2-氨基醇的直接且有力的入口路线。给出了观察结果的合理机械原理，并将反应应用于潜在生物活性靶标的合成。
• Transformation of Amides into Esters by the Use of Chlorotrimethylsilane
  作者：Cuihua Xue、Fen-Tair Luo

  DOI：10.1002/jccs.200400055

  日期：2004.4

  A mild transformation of various amides and imides into the corresponding esters and diesters in good yields by using chlorotrimethylsilane and alcohols at rt are described. Either primary, secondary, or tertiary amide or imide can be used in this transformation. Primary and secondary alcohols gave better yields than tertiary alcohols.

  描述了通过在室温下使用氯三甲基硅烷和醇以良好的收率将各种酰胺和酰亚胺温和地转化为相应的酯和二酯。伯、仲或叔酰胺或酰亚胺均可用于该转化。伯醇和仲醇的产率高于叔醇。