1-Methylpropylcyanamide | 61883-67-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-Methylpropylcyanamide
• 英文别名: N-(sec-butyl)cyanamide；sec-Butylcyanamid；sec-butyl-cyanamide；Cyanamide, (1-methylpropyl)-；butan-2-ylcyanamide
• CAS: 61883-67-8
• 化学式: C₅H₁₀N₂
• 分子量: 98.1478
• InChiKey: ITTXFSDQPGZKKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  116.8±23.0 °C(Predicted)
• 密度：
  0.863±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Methylpropylcyanamide 在 盐酸羟胺 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 N-s-butyl-N'-hydroxyguanidine
  参考文献：
  名称：

  Novel substrates for nitric oxide synthases

  摘要：

  Enzymatic generation of nitric oxide (NO) by nitric oxide synthase (NOS) consists of two oxidation steps. The first step converts L-arginine to N-G-hydroxy-L-arginine (NOHA), a key intermediate, and the second step converts NOHA to NO and L-citrulline. To fully probe the substrate specificity of the second enzymatic step, an extensive structural screening was carried out using a series of N-alkyl (and N-aryl) substituted-N'-hydrosyguanidines (1-14). Among the eleven N-alkyl-N'-hydroxyguanidines evaluated, N-n-propyl (2). N-iso-propyl (3). N-n-butyl (4). N-s-butyl (5). N-iso-butyl (6), N-pentyl (8) and N-iso-pentyl (9) derivatives were efficiently oxidized by the three isoenzymes of NOS (nNOS, iNOS and eNOS) to generate NO. N-Butyl-N'-hydroxyguanidine (4) was the best substrate for iNOS (K-m = 33 muM) and N-iso-propyl-N'-hydroxyguanidine (3) was the best substrate for nNOS (K-m = 56 muM). When the alkyl substituents were too small (such as ethyl 1) or too large (such as hexyl 10 and cyclohexyl 11) the activity decreased significantly. This suggests that the van der Waals interaction between the alkyl group and the hydrophobic cavity in the NOS active site contributes significantly to the relative reactivity of compounds 3-11. Moreover, five N-aryl-N'-hydroxyguanidines were found to be good substrates for iNOS. but not substrates for eNOS and nNOS. N-phenyl-N'-hydroxy- guanidine was the best substrate among them (K-m = 243 muM). This work demonstrates that N-alkyl substituted hydroxyguanidine compounds are novel NOS substrates which 'short-circuit' the first oxidation step of NOS, and N-aryl substituted hydroxyguanidine compounds are isoform selective NOS substrate. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(02)00155-4
• 作为产物：
  描述：

  N-sec-Butyl-benzotriazole-1-carboxamidine 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 1-Methylpropylcyanamide
  参考文献：
  名称：

  Katritzky, Alan R.; Brzezinski, Jacek Z.; Lam, Jamshed N., Revue Roumaine de Chimie, 1991, vol. 36, # 4-7, p. 573 - 580

  摘要：

  DOI：

文献信息

• 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。
• An Improved Synthesis of 2-Amino-1,3-oxazoles under Basic Catalysis
  作者：A. F. COCKERILL、A. DEACON、R. G. HARRISON、D. J. OSBORNE、D. M. PRIME、W. J. ROSS、A. TODD、J. P. VERGE

  DOI：10.1055/s-1976-24127

  日期：——
• COCKERILL A. F.; DEACON A.; HARRISON R. G.; OSBORNE D. J.; PRIME D. M.; R+, SYNTHESIS <SYNT-BF>, 1976 NO 9, 591-593
  作者：COCKERILL A. F.、 DEACON A.、 HARRISON R. G.、 OSBORNE D. J.、 PRIME D. M.、 R+

  DOI：——

  日期：——
• Novel substrates for nitric oxide synthases
  作者：Ming Xian、Noriko Fujiwara、Zhong Wen、Tingwei Cai、Satoshi Kazuma、Adam J Janczuk、Xiaoping Tang、Vladislav V Telyatnikov、Yingxin Zhang、Xinchao Chen、Yasuhide Miyamoto、Naoyuki Taniguchi、Peng George Wang

  DOI：10.1016/s0968-0896(02)00155-4

  日期：2002.9

  Enzymatic generation of nitric oxide (NO) by nitric oxide synthase (NOS) consists of two oxidation steps. The first step converts L-arginine to N-G-hydroxy-L-arginine (NOHA), a key intermediate, and the second step converts NOHA to NO and L-citrulline. To fully probe the substrate specificity of the second enzymatic step, an extensive structural screening was carried out using a series of N-alkyl (and N-aryl) substituted-N'-hydrosyguanidines (1-14). Among the eleven N-alkyl-N'-hydroxyguanidines evaluated, N-n-propyl (2). N-iso-propyl (3). N-n-butyl (4). N-s-butyl (5). N-iso-butyl (6), N-pentyl (8) and N-iso-pentyl (9) derivatives were efficiently oxidized by the three isoenzymes of NOS (nNOS, iNOS and eNOS) to generate NO. N-Butyl-N'-hydroxyguanidine (4) was the best substrate for iNOS (K-m = 33 muM) and N-iso-propyl-N'-hydroxyguanidine (3) was the best substrate for nNOS (K-m = 56 muM). When the alkyl substituents were too small (such as ethyl 1) or too large (such as hexyl 10 and cyclohexyl 11) the activity decreased significantly. This suggests that the van der Waals interaction between the alkyl group and the hydrophobic cavity in the NOS active site contributes significantly to the relative reactivity of compounds 3-11. Moreover, five N-aryl-N'-hydroxyguanidines were found to be good substrates for iNOS. but not substrates for eNOS and nNOS. N-phenyl-N'-hydroxy- guanidine was the best substrate among them (K-m = 243 muM). This work demonstrates that N-alkyl substituted hydroxyguanidine compounds are novel NOS substrates which 'short-circuit' the first oxidation step of NOS, and N-aryl substituted hydroxyguanidine compounds are isoform selective NOS substrate. (C) 2002 Published by Elsevier Science Ltd.
• Katritzky, Alan R.; Brzezinski, Jacek Z.; Lam, Jamshed N., Revue Roumaine de Chimie, 1991, vol. 36, # 4-7, p. 573 - 580
  作者：Katritzky, Alan R.、Brzezinski, Jacek Z.、Lam, Jamshed N.

  DOI：——

  日期：——