N-(3-bromophenyl)-N-methyl-benzamide | 51774-35-7

• 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: N-(3-bromophenyl)-N-methyl-benzamide
• 英文别名: N-(3-bromophenyl)-N-methylbenzamide
• CAS: 51774-35-7
• 化学式: C₁₄H₁₂BrNO
• 分子量: 290.159
• InChiKey: XFHSOIDZRKMHOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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-(3-bromophenyl)-N-methyl-benzamide 在 甲醇 、 copper acetylacetonate 、 水 、 N-氟代双苯磺酰胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以57%的产率得到N-(3-溴苯基)苯甲酰胺
  参考文献：
  名称：

  使用N-氟苯磺酰亚胺作为氧化剂的铜催化酰胺的自由基N-脱甲基化。

  摘要：

  通过在铜催化剂的帮助下使用N-氟苯磺酰亚胺作为氧化剂，已经开发出前所未有的N-甲基酰胺的N-去甲基化。酰胺向甲醇胺的转化涉及连续的单电子转移，氢原子转移和水解，并且伴随着N-（苯磺酰基）苯磺酰胺的形成。甲醇胺由于其固有的不稳定性，会自发分解为N-脱甲基酰胺和甲醛。

  DOI：

  10.1021/acs.orglett.0c00863
• 作为产物：
  描述：

  苯甲酰氯 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 生成 N-(3-bromophenyl)-N-methyl-benzamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Activity of a Novel Series of Human Sirtuin-2-Selective Inhibitors

  摘要：

  Selective inhibitors of human sirtuin 2 (SIRT2), a deacetylase, are candidate therapeutic agents for neurodegenerative diseases such as Parkinson's disease and Huntington's disease as well as potential tools for elucidating the biological functions of SIRT2. On the basis of homology models of SIRT1 and SIRT2, we designed and prepared a series of 2-anilinobenzamide analogues. Enzyme assays using recombinant SIRT1 and SIRT2 revealed that 3'-phenethyloxy-2-anilinobenzamide analogues such as 33a and 33i are potent and selective SIRT2 inhibitors, showing more than 3.5-fold greater SIRT2-inhibitory activity and more than 35-fold greater SIRT2-selectivity compared with AGK2 (3), a previously reported SIRT2-selective inhibitor. Compound 33a also induced a dose-dependent selective increase of alpha-tubulin acetylation in human colon cancer HCT116 cells, indicating selective inhibition of SIRT2 in the cells. These 3'-phenethyloxy-2-anilinobenzamide derivatives represent an entry into a new class of SIRT2-selective inhibitors.

  DOI：

  10.1021/jm3002108

文献信息

• Organic photoredox catalyzed dealkylation/acylation of tertiary amines to access amides
  作者：Chen Liu、Han-Nan Chen、Teng-Fei Xiao、Xiu-Qin Hu、Peng-Fei Xu、Guo-Qiang Xu

  DOI：10.1039/d2cc05842a

  日期：——

  A mild metal-free C–N bond activation strategy for the direct conversion of inert tertiary amines with acyl chlorides into tertiary amides via organic photoredox catalysis is presented. In this protocol, a novel organic photocatalyst (Cz-NI-Ph) that showed excellent catalytic performance during C–N bond cleavage is developed. Moreover, this reaction features green and mild conditions, broad substrate

  提出了一种温和的无金属 C-N 键活化策略，用于通过有机光氧化还原催化将惰性叔胺与酰氯直接转化为叔酰胺。在该协议中，开发了一种新型有机光催化剂 (Cz-NI-Ph)，该催化剂在 C-N 键裂解过程中表现出优异的催化性能。此外，该反应绿色温和，底物适用范围广，原料易得。
• A one-step base-free synthesis of <i>N</i>-arylamides <i>via</i> modified pivaloyl mixed anhydride mediated amide coupling
  作者：Fenghua Mao、Can Jin、Jie Wang、Hui Yang、Xinhuan Yan、Xiaoqing Li、Xiangsheng Xu

  DOI：10.1039/d3ob00452j

  日期：——

  Pivalic anhydride is shown to be an effective reagent for direct amidation of carboxylic acids with N-alkyl anilines. The only by-product of this reaction is nontoxic pivalic acid, which can be easily removed by aqueous workup. The reactions are conducted under mild conditions and found to be compatible with a range of carboxylic acids, including aromatic, heterocyclic, acrylic, and aliphatic carboxylic

  新戊酸酐被证明是一种有效的试剂，可用于羧酸与N-烷基苯胺的直接酰胺化。该反应的唯一副产物是无毒的新戊酸，可以通过水处理轻松去除。该反应在温和条件下进行，发现与一系列羧酸相容，包括芳香族、杂环、丙烯酸和脂肪族羧酸和氨基酸，可在短反应时间内生成所需的酰胺。
• 17β-HSD2 inhibitors for the treatment of osteoporosis: Identification of a promising scaffold
  作者：Marie Wetzel、Sandrine Marchais-Oberwinkler、Rolf W. Hartmann

  DOI：10.1016/j.bmc.2010.12.013

  日期：2011.1

  17 beta-Hydroxysteroid dehydrogenase type 2 (17 beta-HSD2) catalyses the conversion of active 17 beta-hydroxysteroids into the less active 17-ketosteroids thereby controlling the availability of biologically active estrogens (E2) and androgens (T) in the tissues. The skeletal disease osteoporosis occurs mainly in post-menopausal women and in elderly men when the levels of estrogens and androgens, respectively, decrease. Since 17 beta-HSD2 is present in osteoblasts, inhibition of this enzyme may provide a new and promising approach to prevent the onset of osteoporosis, keeping a certain level in estrogens and androgens in bone cells of ageing people. Hydroxynaphthyl, hydroxyphenyl and hydroxymethylphenyl-substituted moieties were synthesised as mimetics of the steroidal substrate. Compound 8 has been identified as promising scaffold for 17 beta-HSD2 inhibitors displaying high activity and good selectivity toward 17 beta-HSD1, ER alpha and ER beta. (C) 2010 Elsevier Ltd. All rights reserved.
• Shpan'ko, I. V.; Litvinenko, L. M.; Goncharov, A. N., Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, p. 847 - 853
  作者：Shpan'ko, I. V.、Litvinenko, L. M.、Goncharov, A. N.、Korzhilova, O. I.

  DOI：——

  日期：——