N-(3-甲基苯基)丁酰胺 | 69833-26-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(3-甲基苯基)丁酰胺
• 英文名称: N-(m-tolyl)butyramide
• 英文别名: butyric acid m-toluidide；N-m-Tolyl-butyramid；Buttersaeure-m-toluidid；N-(3-methylphenyl)butanamide
• CAS: 69833-26-7
• 化学式: C₁₁H₁₅NO
• mdl: MFCD00791303
• 分子量: 177.246
• InChiKey: HHJVHZGGWADBKL-UHFFFAOYSA-N

物化性质

• 保留指数：
  1597

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 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-(3-甲基苯基)丁酰胺 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 N-丁基间甲苯胺
  参考文献：
  名称：

  Benedini, Francesca; Galliani, Guido; Nali, Micaela, Journal of the Chemical Society. Perkin transactions II, 1985, p. 1963 - 1968

  摘要：

  DOI：
• 作为产物：
  描述：

  3-硝基甲苯 、 丁酰氯 在 溶剂黄146 、 三乙胺 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以51%的产率得到N-(3-甲基苯基)丁酰胺
  参考文献：
  名称：

  Reductive amidation of nitroarenes: a practical approach for the amidation of natural products

  摘要：

  A simple and practical approach for the one-pot conversion of nitroarenes into amide derivatives has been developed. Zinc and acetic acid are utilized as a reducing agent, and acyl chloride and triethylamine are used as the acylating agent in DMF with good yield (similar to 60%) of the amide. This method was applicable to manzamine A (1), where the yield of 6-cyclohexamidemanzamine A (7) was significantly improved (56%) by this approach relative to (17%) by beginning with the amine. (c) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2009.04.061

文献信息

• Palladium(II)-Catalyzed Oxidative Homo- and Cross-Coupling of Aryl <i>ortho</i>-sp² C–H Bonds of Anilides at Room Temperature
  作者：Chong Mei、Wenjun Lu

  DOI：10.1021/acs.joc.8b00120

  日期：2018.4.20

  The preparation of secondary 2,2′-bisanilides has been successfully achieved through an oxidative coupling of aryl ortho-sp2 C–H bonds of anilides in the presence of catalytic Pd(OAc)2 and K2S2O8 as an oxidant in MsOH/CF3CO2H (TFA) at room temperature (25 °C). The aromatic rings of anilides substituted by various electron-donating or electron-withdrawing groups are tolerant in these coupling reactions

  通过在催化性Pd（OAc）2和K 2 S 2 O 8作为氧化剂的存在下，通过对苯甲酸酯的芳基邻-sp 2 C-H键进行氧化偶联，成功地完成了2,2'-双苯胺的制备。在室温（25°C）下在MsOH / CF 3 CO 2 H（TFA）中溶解。在这些偶联反应中，被各种给电子或吸电子基团取代的苯甲酸酯的芳环是可容忍的。
• Organocatalytic Asymmetric Annulation between Hydroxymaleimides and Nitrosoarenes: Stereoselective Preparation of Chiral Quaternary <i>N</i>-Hydroxyindolines
  作者：Yu Yang、Hong-Xia Ren、Feng Chen、Zheng-Bing Zhang、Ying Zou、Chao Chen、Xiang-Jia Song、Fang Tian、Lin Peng、Li-Xin Wang

  DOI：10.1021/acs.orglett.7b00893

  日期：2017.6.2

  highly effective asymmetric annulation of nitrosoarenes with hydroxymaleimides catalyzed by a chiral bifunctional amine squaramide catalyst has been disclosed. A wide range of highly fused chiral N-hydroxyindolines with two consecutive quaternary stereocenters and multifunctional groups were directly and effectively prepared in excellent yields (up to >99%) with complete regioselective cyclization and

  已公开了一种由手性双官能胺方酸方胺催化剂催化的亚硝基芳烃与羟基马来酰亚胺的不寻常且高度有效的不对称环化反应。直接和有效地制备了具有两个连续的季位立体中心和多功能基团的各种高度融合的手性N-羟基二氢吲哚，具有良好的收率（高达99％），具有完全的区域选择性环化和出色的立体选择性（高达> 99：1 dr 99％ee）。通过精细地转化为一系列新的手性二氢吲哚，可以很好地证明新反应和目标手性实体的效率和潜力。
• Organocatalytic and enantioselective [4+2] cyclization between hydroxymaleimides and <i>ortho</i>-hydroxyphenyl <i>para</i>-quinone methide-selective preparation of chiral hemiketals
  作者：Min Xiang、Chen-Yi Li、Xiang-Jia Song、Ying Zou、Zhi-Cheng Huang、Xia Li、Fang Tian、Li-Xin Wang

  DOI：10.1039/d0cc06777f

  日期：——

  A highly effective and enantioselective organocatalytic [4+2] cyclization has been disclosed, and a series of new chiral hemiketals containing chromane and succinimide frameworks have been firstly prepared in excellent results with 100% atom efficacy.

  已披露了一种高效的和对映选择性的有机催化[4+2]环化反应，首次制备了一系列含有色酮和琥珀酰亚胺骨架的新手性半酮，其结果优异，原子效率达到100%。
• IMPROVEMENTS IN OR RELATING TO ENCAPSULATED PERFUME COMPOSITIONS
  申请人：Givaudan SA

  公开号：EP3310892B1

  公开（公告）日：2019-10-23
• EP3757179A1
  申请人：——

  公开号：EP3757179A1

  公开（公告）日：2020-12-30