N-cyclohexyl-N-[(cyclohexylamino)carbonyl]-ω-undecenemide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: N-cyclohexyl-N-[(cyclohexylamino)carbonyl]-ω-undecenemide
• 英文别名: 1-(undec-10-enoyl)-1,3-dicyclohexylurea；N-cyclohexyl-N-(cyclohexylcarbamoyl)undec-10-enamide
• 化学式: C₂₄H₄₂N₂O₂
• 分子量: 390.61
• InChiKey: GWAPVSASNIVCFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-十一烯酸 、 2-氨基苯酚 、 N,N'-二环己基碳二亚胺 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以47%的产率得到N-(2-hydroxyphenyl)undec-10-enamide
  参考文献：
  名称：

  A facile, one-pot synthesis, characterization and antimicrobial activity of o-hydroxy anilide derivatives and 1-substituted-1,3-dicyclohexylurea analogs of long chain carboxylic acids

  摘要：

  A series of novel o-hydroxy anilide derivatives and 1-substituted-1,3-dicyclohexylurea analogs of long chain carboxylic acids have been synthesized. The structures of the synthesized compounds were elucidated by IR, H-1 NMR, C-13 NMR and mass spectral data. All the synthesized compounds were tested for their antimicrobial activity by disk diffusion assay with slight modifications against Gram-positive, Gram-negative strains of bacteria as well as fungal strains. After that mini mum inhibitory concentrations (MICs), minimum bactericidal concentrations (MBCs) and minimum fungicidal concentrations (MFCs) of all the synthesized compounds were determined. The investigation of antimicrobial screening data revealed that all the tested compounds showed moderate to good microbial inhibitions. Compounds 3e, 4e, 3f and 4f were found to be the most potent antimicrobial agents. (c) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.070

文献信息

• Total Synthesis of Korormicin
  作者：Yuichi Kobayashi、Shinya Yoshida、Yuji Nakayama

  DOI：10.1002/1099-0690(200105)2001:10<1873::aid-ejoc1873>3.0.co;2-o

  日期：2001.5

  (5S)-4 and both enantiomers of acid 5 and of boronate ester 7. Lactone (5S)-4 and boronate 7 with (9′S,10′R) and (9′R,10′S) chiralities were prepared through asymmetric dihydroxylation of olefins 11 and 30, respectively, with AD-mix-α or -β. Compounds (3′R)- and (3′S)-5 were prepared by kinetic resolution of rac-19 with asymmetric epoxidation. Condensation of (5S)-4 and (3′R)- or (3′S)-5 with DCC in the

  最近，我们根据四种可能的非对映异构体的比旋光度将 (5S,3'R,9'S,10'R) 立体化学分配给平面 korormicin (1) [即 (5S,3'R, 9'S,10'R)、(5S,3'S,9'S,10'R)、(5S,3'S,9'R,10'S) 和 (5S,3'R,9 'R,10'S) 异构体]，通过全合成制备。在本文中，我们详细描述了合成方面。合成中的中间体是烯氨基内酯 (5S)-4 以及酸 5 和硼酸酯 7 的两种对映异构体。内酯 (5S)-4 和硼酸酯 7 与 (9'S,10'R) 和 (9'R, 10'S) 手性是通过烯烃 11 和 30 分别与 AD-mix-α 或 -β 的不对称二羟基化制备的。化合物 (3'R)- 和 (3'S)-5 通过 rac-19 的不对称环氧化动力学拆分制备。(5S)-4 和 (3'R)- 或 (3'S)-5 在 DMAP 和 PPTS 存在下与
• Selective esterifications of alcohols and phenols through carbodiimide couplingsElectronic supplementary information (ESI) available: the characterization of new compounds and literature references for known compounds. See http://www.rsc.org/suppdata/ob/b3/b312559a/
  作者：Rimma Shelkov、Moshe Nahmany、Artem Melman

  DOI：10.1039/b312559a

  日期：——

  Esterification of carboxylic acids capable of forming ketene intermediates upon treatment with carbodiimides permits the selective acylation of alcohols in the presence of phenols lacking strong electron-withdrawing groups. The selectivity of acylations involving highly acidic phenols could be reversed through the addition of catalytic amount of acid. Esterification of other carboxylic acids was found

  在用碳二亚胺处理后能够形成烯酮中间体的羧酸的酯化反应可在缺乏强吸电子基团的酚存在下对醇进行选择性酰化。可以通过添加催化量的酸来逆转涉及高酸性酚的酰化反应的选择性。发现其他羧酸的酯化反应通过对称酸酐的形成进行，并提供相反的化学选择性。在这两种情况下，取代酚的相对酰化速率均与反应机理一致，该机理涉及酚盐阴离子攻击亲电子中间体（例如乙烯酮和对称酸酐），而碳二亚胺既用作活化剂，又用作碱性催化剂。
• A facile, one-pot synthesis, characterization and antimicrobial activity of o-hydroxy anilide derivatives and 1-substituted-1,3-dicyclohexylurea analogs of long chain carboxylic acids
  作者：Nida N. Farshori、Anis Ahmad、Asad U. Khan、Abdul Rauf

  DOI：10.1016/j.ejmech.2011.01.070

  日期：2011.4

  A series of novel o-hydroxy anilide derivatives and 1-substituted-1,3-dicyclohexylurea analogs of long chain carboxylic acids have been synthesized. The structures of the synthesized compounds were elucidated by IR, H-1 NMR, C-13 NMR and mass spectral data. All the synthesized compounds were tested for their antimicrobial activity by disk diffusion assay with slight modifications against Gram-positive, Gram-negative strains of bacteria as well as fungal strains. After that mini mum inhibitory concentrations (MICs), minimum bactericidal concentrations (MBCs) and minimum fungicidal concentrations (MFCs) of all the synthesized compounds were determined. The investigation of antimicrobial screening data revealed that all the tested compounds showed moderate to good microbial inhibitions. Compounds 3e, 4e, 3f and 4f were found to be the most potent antimicrobial agents. (c) 2011 Elsevier Masson SAS. All rights reserved.