N-isopropyl-3-phenylbutanamide | 103818-68-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-isopropyl-3-phenylbutanamide
• 英文别名: 3-phenyl-N-(propan-2-yl)butanamide；3-phenyl-N-propan-2-ylbutanamide
• CAS: 103818-68-4
• 化学式: C₁₃H₁₉NO
• mdl: MFCD03576329
• 分子量: 205.3
• InChiKey: IAADGNRUCRJGLD-UHFFFAOYSA-N

物化性质

• 沸点：
  359.1±21.0 °C(Predicted)
• 密度：
  0.969±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-isopropyl-3-phenylbutanamide 在 仲丁基锂 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 18.83h， 生成 4-methyl-4,5-diphenyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Synthetic Applications of the β-Lithiation of β-Aryl Secondary Amides:  Diastereoselective and Enantioselective Substitutions

  摘要：

  The sequence of beta-lithiation and electrophilic substitution of beta-aryl secondary amides is reported. The lithiations occur regioselectively at the beta-position, and the resulting lithiated intermediates can be reacted with a wide range of electrophiles to give substituted products. Reactions of beta-lithiated amides bearing an alpha-substituent provide substituted products with high diastereoselectivity, Electrophilic substitutions of beta-lithiated N-methylamides in the presence of the chiral diamine (-)-sparteine provide highly enantioenriched products. The methodology is used to synthesize enantioenriched beta-aryl beta-substituted amides, acids, and lactones.

  DOI：

  10.1021/jo952223r
• 作为产物：
  描述：

  在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以15%的产率得到N-isopropyl-3-phenylbutanamide
  参考文献：
  名称：

  The Favorskii rearrangement of .alpha.-chloro ketimines

  摘要：

  DOI：

  10.1021/jo00370a018

文献信息

• Ketone Synthesis by Direct, Orthogonal Chemoselective Hydroacylation of Alkenes with Amides: Use of Alkenes as Surrogates of Alkyl Carbanions
  作者：Hui Geng、Pei‐Qiang Huang

  DOI：10.1002/cjoc.201900252

  日期：2019.8

  and direct transformation of carboxamides are two exciting areas that have attracted considerable attention in recent years. We report herein that secondary amides, the least reactive derivatives of carbonyl compounds, upon activated with triflic anhydride, can serve as effective hydroacylating reagents in partner with alkenes to yield ketones at ambient temperature. The method was applied to the one‐step

  烯烃的直接官能化和羧酰胺的直接转化是近年来令人瞩目的两个令人兴奋的领域。我们在此报道，仲酰胺，即羰基化合物的反应性最低的衍生物，在用三氟甲磺酸酐活化后，可以与烯烃一起作为有效的氢酰化试剂，在环境温度下产生酮。该方法已用于外消旋二氢芳基羟色酮的一步合成。在这种方法中，烯烃用作有机金属试剂的替代物，从而可以进行正交的化学选择性反应。许多烯烃（如camp烯和降冰片烯）的现成性允许一步合成酮，而传统方法则需要几个步骤。
• Iridium-Catalyzed Reductive Alkylations of Secondary Amides
  作者：Wei Ou、Feng Han、Xiu-Ning Hu、Hang Chen、Pei-Qiang Huang

  DOI：10.1002/anie.201806747

  日期：2018.8.27

  Reported herein is the first direct, metal‐catalyzed reductive functionalization of secondary amides to give functionalized amines and heterocycles. The method is shown to have exceptionally broad scope with respect to suitable nucleophiles, which cover both hard and soft C nucleophiles as well as a P nucleophile. The reaction exhibits good chemoselectivity and tolerates several sensitive functional

  本文报道的是仲酰胺的第一个直接的，金属催化的还原性官能化反应，以生成官能化的胺和杂环。相对于合适的亲核试剂，该方法具有广泛的适用范围，既涵盖硬C亲核试剂，也包括软C亲核试剂和P亲核试剂。该反应表现出良好的化学选择性，并能耐受几个敏感的官能团。
• A General Method for the One-Pot Reductive Functionalization of Secondary Amides
  作者：Pei-Qiang Huang、Ying-Hong Huang、Kai-Jiong Xiao、Yu Wang、Xiao-Er Xia

  DOI：10.1021/jo502929x

  日期：2015.3.6

  A one-pot reaction for the transformation of common secondary amides into amines with C–C bond formation is described. This method consists of in situ amide activation with Tf2O–partial reduction–addition of C-nucleophiles. The method is general in scope, which allows employing both hard nucleophiles (RMgX, RLi) and soft nucleophiles, as well as enolates. With the use of soft nucleophiles, the reaction

  描述了一锅反应，可将常见的仲酰胺转化为具有C-C键的胺。该方法包括的原位酰胺活化与TF 2 O形部分还原加成的Ç -nucleophiles。该方法的范围很广，可以同时使用硬亲核试剂（RMgX，RLi）和软亲核试剂以及烯醇盐。使用软的亲核试剂，在酯，氰基，硝基和叔酰胺基团存在的情况下，反应在仲酰胺上以高化学选择性进行。
• Dihydroxypyrimidine carboxamide inhibitors of HIV integrase
  申请人：Di Francesco E. Maria

  公开号：US20070083045A1

  公开（公告）日：2007-04-12

  4,5-Dihydroxypyrimidine-6-carboxamides of formula: are described as inhibitors of HIV integrase and inhibitors of HIV replication, wherein R 1 , R 2 , R 3 and R 4 are defined herein. These compounds are useful in the prevention and treatment of infection by HIV and in the prevention, delay in the onset, and treatment of AIDS. The compounds are employed against HIV infection and AIDS as compounds per se or in the form of pharmaceutically acceptable salts. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of preventing, treating or delaying the onset of AIDS and methods of preventing or treating infection by HIV are also described.

  本文描述了式子中R1，R2，R3和R4被定义的4,5-二羟基嘧啶-6-羧酰胺化合物，其作为HIV整合酶抑制剂和HIV复制抑制剂。这些化合物对于预防和治疗HIV感染以及预防、延迟AIDS发病和治疗AIDS非常有用。这些化合物可以作为化合物本身或药物可接受的盐形式用于对抗HIV感染和AIDS。这些化合物及其盐可以与其他抗病毒药物、免疫调节剂、抗生素或疫苗组合使用，作为制药组合物的成分。本文还描述了预防、治疗或延迟AIDS发病以及预防或治疗HIV感染的方法。
• US7459452B2
  申请人：——

  公开号：US7459452B2

  公开（公告）日：2008-12-02