N-(methoxycarbonylamino)cyclohexylamine | 24537-42-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(methoxycarbonylamino)cyclohexylamine
• 英文别名: methyl 2-cyclohexylhydrazinecarboxylate；methyl N-(cyclohexylamino)carbamate
• CAS: 24537-42-6
• 化学式: C₈H₁₆N₂O₂
• 分子量: 172.227
• InChiKey: HAEQORGQZSXNEA-UHFFFAOYSA-N

物化性质

• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(methoxycarbonylamino)cyclohexylamine 在 lead(IV) acetate 作用下， 以 二氯甲烷 为溶剂， 生成 methyl N-cyclohexyliminocarbamate
  参考文献：
  名称：

  Diazenes. VI. Alkyldiazenes

  摘要：

  DOI：

  10.1021/ja00737a025
• 作为产物：
  描述：

  carbomethoxyhydrazone of cyclohexanone 在 镍 氢气 作用下， 以 乙醇 为溶剂， 生成 N-(methoxycarbonylamino)cyclohexylamine
  参考文献：
  名称：

  Diazenes. VI. Alkyldiazenes

  摘要：

  DOI：

  10.1021/ja00737a025

文献信息

• N-amination using N-methoxycarbonyl-3-phenyloxaziridine. Direct access to chiral N_β-protected α-hydrazinoacids and carbazates
  作者：Joëlle Vidal、Jacques Drouin、André Collet

  DOI：10.1039/c39910000435

  日期：——

  Primary and secondary amines N–H, including α-aminoacids, can be converted under mild conditions to the corresponding carbazates N–NH–CO2Me, on reaction with N-methoxycarbonyl-3-phenyloxaziridine 1.

  初级和次级胺的 N–H，包括 α-氨基酸，可以在温和条件下与 N-甲氧基碳酰基-3-苯基呋喃啶 1 反应，转化为相应的脲体 N–NH–CO2Me。
• N-Alkyloxycarbonyl-3-aryloxaziridines: Their Preparation, Structure, and Utilization As Electrophilic Amination Reagents
  作者：Joëlle Vidal、Stéphanie Damestoy、Laure Guy、Jean-Christophe Hannachi、André Aubry、Andreé Collet、André Aubry

  DOI：10.1002/chem.19970031019

  日期：1997.10

  AbstractThis paper reports the synthesis of a series of N‐protected oxaziridines (N‐Moc, Boc, Z or Fmoc) and discusses their ability to deliver their N‐alkoxycar‐bonyl fragment to amines, enolates, sulfur, and phosphorus nucleophiles (electrophilic amination). These oxaziridines are prepared by oxidation of the corresponding imines with oxone or anhydrous MCPBA lithium salt as the source of oxygen. They transfer their N‐protected fragment to primary and secondary amines to give protected hydrazines in fair to excellent yield. The nitrogen transfer to free amino acids (in form of their R4N+ salts) is particularly fast, even at low temperature, providing L (or D) N‐protected α‐hydrazino acids. Enolates are C‐aminated to give N‐protected α‐amino ketones, esters, or amides in modest yield, due to a side aldol reaction of the unreacted enolate with the released benzaldehyde. With tertiary amines (Et3N), sulfides (PhSMe), and phosphines (Ph3P), amination and oxidation proceed in a parallel way; the amount of amination product increases when the temperature is lowered (kinetic control). Some of the factors that can orient the oxaziridine reactivity towards amination or oxidation of nucleophiles are considered.
• Chiral 1,3,4-Oxadiazol-2-ones as Highly Selective FAAH Inhibitors
  作者：Jayendra Z. Patel、Teija Parkkari、Tuomo Laitinen、Agnieszka A. Kaczor、Susanna M. Saario、Juha R. Savinainen、Dina Navia-Paldanius、Mariateresa Cipriano、Jukka Leppänen、Igor O. Koshevoy、Antti Poso、Christopher J. Fowler、Jarmo T. Laitinen、Tapio Nevalainen

  DOI：10.1021/jm400923s

  日期：2013.11.14

  In the present study, identification of chiral 1,3,4-oxadiazol-2-ones as potent and selective FAAH inhibitors has been described. The separated enantiomers showed clear differences in the potency and selectivity toward both FAAH and MAGL. Additionally, the importance of the chirality on the inhibitory activity and selectivity was proven by the simplification approach by removing a methyl group at the 3-position of the 1,3,4-oxadiazol-2-one ring. The most potent compound of the series, the S-enantiomer of 3-(1-(4-isobutylphenyl)ethyl)-5-methoxy-1,3,4-oxadiazol-2(3H)-one (JZP-327A, 51), inhibited human recombinant FAAH (hrFAAH) in the low nanomolar range (IC50 = 11 nM), whereas its corresponding R-enantiomer 52 showed only moderate inhibition toward hrFAAH (IC50 = 0.24 mu M). In contrast to hrFAAH, R-enantiomer 52 was more potent in inhibiting the activity of hrMAGL compared to S-enantiomer 51 (IC50 = 4.0 mu M and 16% inhibition at 10 mu M, respectively). The FAAH selectivity of the compound Si over the supposed main off-targets, MAGL and COX, was found to be >900-fold. In addition, activity-based protein profiling (ABPP) indicated high selectivity over other serine hydrolases. Finally, the selected S-enantiomers 51, 53, and 55 were shown to be tight binding, slowly reversible inhibitors of the hrFAAH.
• Diazenes. VI. Alkyldiazenes
  作者：Edward M. Kosower、Takashi Tsuji

  DOI：10.1021/ja00737a025

  日期：1971.4