N-methyl-N-phenylcinnamamide | 27687-46-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-methyl-N-phenylcinnamamide
• 英文别名: 2-Propenamide, N-methyl-N,3-diphenyl-；N-methyl-N,3-diphenylprop-2-enamide
• CAS: 27687-46-3
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: BLOBGBACNLKBAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-methyl-N-phenylcinnamamide 在 aluminum (III) chloride 作用下， 以 氯苯 为溶剂， 反应 5.0h， 生成 1-甲基-2-喹啉酮
  参考文献：
  名称：

  Heterocoumarins Are Selective Carbonic Anhydrase IX and XII Inhibitors with Cytotoxic Effects against Cancer Cells Lines

  摘要：

  We have synthesized a new series of coumarin-based compounds demonstrating high selectivity and potent effects with low nanomolar affinity against the tumor associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA IX and XII. A number of these compounds were evaluated ex vivo against human prostate (PC3) and breast (MDA-MB-231) cancer cell lines. Compounds 4b and 15 revealed effective cytotoxic effects after 48 h of incubation in both normoxic and hypoxic conditions with PC3 cancer cell line. However, compound 3 showed selective cytotoxic effects against MDA-MB-231 in hypoxic condition. These results may be of particular importance for the choice of future drug candidates targeting hypoxic tumors and metastases, considering the fact that a selective carbonic anhydrase CA IX inhibitor (SLC-0111) is presently in phase II clinical trials.

  DOI：

  10.1021/acsmedchemlett.8b00362
• 作为产物：
  描述：

  N-苯基甲亚胺 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 N-methyl-N-phenylcinnamamide
  参考文献：
  名称：

  两个连续的钯（II）促进的CH烯基化反应，用于合成3-烯基喹诺酮

  摘要：

  AbstractHighly substituted quinolones are obtained through an efficient and atom economical procedure that involves two consecutive palladium(II)‐catalyzed CH alkenylation reactions. A selective 6‐endo intramolecular CH alkenylation leads to 4‐substituted quinolones that have been further functionalized at C‐3 through a second intermolecular CH alkenylation reaction.magnified image

  DOI：

  10.1002/adsc.201400931
• 作为试剂：
  描述：

  tert-butyl 2-(1,3-dioxoisoindolin-2-yl)ethaneperoxoate 、 2,6-二叔丁基-4-甲基苯酚 在 iron(II) chloride tetrahydrate 、 N-methyl-N-phenylcinnamamide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  FeCl 2催化肉桂酰胺的脱羧自由基烷基化/环化反应：获得二氢喹啉酮和吡咯并[1,2- a ]吲哚类似物

  摘要：

  开发了一种简单且统一的方法，以中等至高收率（高达91％）合成具有非对映选择性（> 20：1 dr）的烷基化二氢喹啉酮和吡咯并[1,2- a ]吲哚衍生物。廉价的FeCl 2 ·4H 2 O用作催化剂，由脂肪酸容易制得的过酸酯（或过氧化物）用作烷基化试剂和单电子氧化剂。该环境友好的反应通过FeCl 2催化的烷基自由基级联加成/环化方式进行。

  DOI：

  10.1021/acs.joc.8b00511

文献信息

• nBu4NI-catalyzed oxidative amidation of aldehydes with tertiary amines
  作者：Shan Wang、Jian Wang、Rui Guo、Gao Wang、Shan-Yong Chen、Xiao-Qi Yu

  DOI：10.1016/j.tetlet.2013.09.018

  日期：2013.11

  An efficient oxidative coupling protocol for amide formation has been developed. Various tertiary amines and aromatic aldehydes were oxidized to their corresponding tertiary amides in moderate to good yields in the presence of a simple nBu4NI-catalyst.

  已经开发了用于酰胺形成的有效的氧化偶联方案。在简单的n Bu 4 NI催化剂存在下，各种叔胺和芳族醛以中等到良好的收率被氧化成它们相应的叔酰胺。
• Oxindole synthesis by palladium-catalysed aromatic C–H alkenylation
  作者：Satoshi Ueda、Takahiro Okada、Hideko Nagasawa

  DOI：10.1039/b926560k

  日期：——

  A strategy involving palladium-catalysed aromatic C-H functionalisation/intramolecular alkenylation provides a convenient and direct synthesis of 3-alkylideneoxindoles. In the presence of 5 mol% of PdCl(2)MeCN(2) and AgOCOCF(3), a wide variety of N-cinnamoylanilines gave 3-alkylideneoxindoles in moderate to good yield.

  涉及钯催化的芳族CH官能化/分子内烯基化的策略提供了3-亚烷基亚氧吲哚的方便和直接的合成。在5 mol％的PdCl（2）MeCN（2）和AgOCOCF（3）的存在下，各种各样的N-肉桂酰基苯胺以中等至良好的收率得到3-亚烷基亚甲基吲哚。
• Fe-Catalyzed decarbonylative cascade reaction of <i>N</i>-aryl cinnamamides with aliphatic aldehydes to construct 3,4-dihydroquinolin-2(1<i>H</i>)-ones
  作者：Ru-Xin Gao、Xin-Qi Luan、Zi-Yi Xie、Luo Yang、Yong Pei

  DOI：10.1039/c9ob00492k

  日期：——

  A practical Fe-catalyzed decarbonylative cascade reaction of N-aryl cinnamamides with aliphatic aldehydes to provide C3 alkylated 3,4-dihydroquinolin-2(1H)-ones is developed. Aliphatic aldehydes were oxidatively decarbonylated into 1°, 2° and 3° alkyl radicals conveniently, allowing for the subsequent cascade construction of C(sp3)-C(sp3) and C(sp3)-C(sp2) bonds via radical addition and HAS-type cyclization

  开发了一种实用的Fe催化的N-芳基肉桂酰胺与脂肪族醛的脱羰级联反应，以提供C3烷基化的3,4-二氢喹啉-2（1H）-酮。脂肪醛可方便地氧化脱羰成1°，2°和3°烷基，从而可通过自由基加成和HAS随后进行C（sp3）-C（sp3）和C（sp3）-C（sp2）键的级联构造型环化。通过实验结果和DFT计算，阐明了酰胺键的重要性和6-内-trig对5-exo-trig环化途径的选择性。
• Synthesis of Oxindoles by Iron-Catalyzed Oxidative 1,2-Alkylarylation of Activated Alkenes with an Aryl C(sp²)H Bond and a C(sp³)H Bond Adjacent to a Heteroatom
  作者：Wen-Ting Wei、Ming-Bo Zhou、Jian-Hong Fan、Wei Liu、Ren-Jie Song、Yu Liu、Ming Hu、Peng Xie、Jin-Heng Li

  DOI：10.1002/anie.201210029

  日期：2013.3.25

  Difunctionalization: Inexpensive and environmentally benign FeCl3 catalyzes the oxidative 1,2‐alkylarylation of activated alkenes with an aryl C(sp2)H bond and a C(sp3)H bond adjacent to a heteroatom. This reaction is a new strategy for the synthesis of oxindoles and makes use of DBU as ligand and TBHP as oxidant (see scheme, TBHP=tert‐butyl hydrogenperoxide).

  双官能化：廉价且对环境无害的FeCl 3催化带有芳基C（sp 2）H键和邻近杂原子的C（sp 3）H键的活化烯烃的氧化1,2-烷基芳基化。该反应是合成羟吲哚的新策略，它利用DBU作为配体，TBHP作为氧化剂（参见方案TBHP =叔丁基过氧化氢）。
• Molecular Oxygen-Promoted General and Site-Specific Alkylation with Organoboronic Acid
  作者：Anbo Ling、Lizhi Zhang、Ren Xiang Tan、Zhong-Quan Liu

  DOI：10.1021/acs.joc.8b02277

  日期：2018.12.7

  alkylating method using organoboronic acid under 1 atm of oxygen is developed. It allows a facile access to a wide range of functionalized molecules with privileged scaffolds in drugs and natural products such as oxindoles, quinolinones, chromones, naphthoquinones, coumarins, and quinolones. In contrast to previous alkylation approaches that generally requiring transition-metal catalysis and a stoichiometric

  提出了在1个大气压的氧气下使用有机硼酸的常规烷基化方法。它允许轻松访问药物和天然产物（例如羟吲哚，喹啉酮，色酮，萘醌，香豆素和喹诺酮）中具有特权的支架的各种功能化分子。与通常需要过渡金属催化和化学计量的化学氧化剂的以前的烷基化方法相反，本发明的策略以无金属的分子氧作为末端氧化剂和位点特异性为特征。