N-butyl-N-phenylcyanamide | 20914-21-0

• 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-butyl-N-phenylcyanamide
• 英文别名: butyl-phenyl-carbamonitrile；Butyl-phenyl-carbamonitril；Butyl-phenyl-cyanamid；N-Butyl-N-cyan-anilin；Butyl(phenyl)cyanamide
• CAS: 20914-21-0
• 化学式: C₁₁H₁₄N₂
• 分子量: 174.246
• InChiKey: SMPBBSKNRFYRRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-butyl-N-phenylcyanamide 、 正丁醇 在 sodium butanolate 作用下， 以 苯 为溶剂， 生成 N.O-Dibutyl-N-phenyl-isoharnstoff
  参考文献：
  名称：

  Chemistry of Pseudoureas¹

  摘要：

  DOI：

  10.1021/jo01045a041
• 作为产物：
  描述：

  N-丁基苯胺 生成 N-butyl-N-phenylcyanamide
  参考文献：
  名称：

  v. Braun; Fussgaenger; Kuehn, Justus Liebigs Annalen der Chemie, 1925, vol. 445, p. 214

  摘要：

  DOI：

文献信息

• Palladium-Catalyzed Arylation of Cyanamides
  作者：Ryan M. Stolley、Wenxing Guo、Janis Louie

  DOI：10.1021/ol203069p

  日期：2012.1.6

  The cross-coupling of alkyl cyanamides with a number of aryl, heteroaryl, and vinyl halide and pseudohalide coupling partners has been developed via a modification of Pd-catalyzed amidation methods. The reactions proceed selectively under mild conditions with reasonable reaction times in moderate to excellent yields.

  烷基氰胺与许多芳基、杂芳基和乙烯基卤化物和拟卤化物偶联伙伴的交叉偶联已通过对 Pd 催化的酰胺化方法的改进而开发。反应在温和条件下选择性进行，反应时间合理，产率中等至极好。
• Transition-metal free N-arylation of cyanamides by diaryliodonium triflates in aqueous media
  作者：Jihui Li、Xinyi Zheng、Wei Li、Wei Zhou、Wen Zhu、Yucang Zhang

  DOI：10.1039/c5nj02153g

  日期：——

  protocol is established for the synthesis of disubstituted cyanamides through the transition-metal free N-arylation of cyanamides by diaryliodonium triflates in aqueous media. Both alkyl and aryl cyanamides are well compatible with the mild reaction conditions. The one-pot synthesis of ureas is also possible through sequential arylation and hydrolysis of cyanamides, diaryliodonium triflates and H2O

  建立了一种操作简单的方案，用于通过在水介质中使用二芳基碘鎓三氟甲磺酸盐通过氰化物的无过渡金属的N-芳基化来合成二取代的氰胺。烷基和芳基氰酰胺都与温和的反应条件完全相容。一锅法合成尿素也可以通过连续的芳基化和氰化物，二芳基二铵三氟甲磺酸盐和H 2 O的水解来进行，并具有良好的收率。
• HETEROCYCLIC DERIVATIVE HAVING INHIBITORY ACTIVITY ON TYPE-I 11 DATA-HYDROXYSTEROID DEHYDROGENASE
  申请人：Itai Akiko

  公开号：US20100234363A1

  公开（公告）日：2010-09-16

  Disclosed is a compound which is useful as an 11β-hydroxysteroid dehydrogenase type 1 inhibitor. A compound represented by the formula: its pharmaceutically acceptable salt, or a solvate thereof, wherein X is O or S, a broken line and a wavy line represent the presence or the absence of a bond, (i) when a broken line represents the presence of a bond, a wavy line represents the absence of a bond, R 2 and R 3 are each independently hydrogen, halogen, cyano, hydroxy, carboxy, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl or the like, (ii) when a broken line represents the absence of a bond, a wavy line represents the presence of a bond, R 1 and R 4 are each independently hydrogen, halogen or the like, R 2 and R 3 are each independently hydrogen, halogen, cyano, hydroxy, carboxy, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl or the like, and R 5 and R 6 are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl or the like.

  本发明涉及一种化合物，可用作11β-羟基类固醇脱氢酶1型抑制剂。化合物的表示式如下：其药学上可接受的盐或其溶剂化物，其中X为O或S，一条断线和一条波浪线分别表示键的存在或不存在，(i) 当断线表示键的存在时，波浪线表示键的不存在，R2和R3各自独立地表示氢、卤素、氰基、羟基、羧基、可选取代的烷基、可选取代的烯基、可选取代的炔基或类似物，(ii) 当断线表示键的不存在时，波浪线表示键的存在，R1和R4各自独立地表示氢、卤素或类似物，R2和R3各自独立地表示氢、卤素、氰基、羟基、羧基、可选取代的烷基、可选取代的烯基、可选取代的炔基或类似物，而R5和R6各自独立地表示氢、可选取代的烷基、可选取代的烯基、可选取代的炔基或类似物。
• Copper-Catalyzed, Ligand-Controlled N(sp³)- or N(sp)-Selective Arylation of Cyanamides
  作者：Jiaqi Fang、Oumaïma Bekkouch、Guilhem Zeiser、Yurii Zubchuk、Vincent Bizet、Nicolas Blanchard、Gwilherm Evano

  DOI：10.1021/acs.orglett.3c02622

  日期：2023.9.1

  both nucleophilic and electrophilic centers, and their arylation reactions are known to proceed at N(sp3) and C(sp) sites, leading to N-aryl cyanamides or amidines. N(sp) selectivity has also been reported only in the presence of amines, thus leading to guanidines. Herein, we report a general copper-catalyzed ligand-controlled Chan-Lam-Evans arylation of cyanamides proceeding regioselectively at the N(sp3)

  氰胺同时具有亲核和亲电子中心，并且已知它们的芳基化反应在N(sp 3 )和C(sp)位点进行，产生N-芳基氰胺或脒。据报道，N(sp) 选择性仅在胺存在下产生，从而产生胍。在此，我们报道了一般的铜催化配体控制的氰胺的Chan-Lam-Evans芳基化反应，该反应在N(sp 3 )或N(sp)原子上进行区域选择性，并产生N-芳基氰胺或不对称碳二亚胺。配体（联吡啶或二胺）的性质控制产物分布，从而提供从容易获得的氰胺到有用结构单元的不同入口。
• Chemistry of Pseudoureas¹
  作者：Sylvan E. Forman、Clifford A. Erickson、Herman Adelman

  DOI：10.1021/jo01045a041

  日期：1963.10