N-cyclobutylformamide | 87055-64-9

• 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-cyclobutylformamide
• 英文别名: N-Cyclobutyl-formamide
• CAS: 87055-64-9
• 化学式: C₅H₉NO
• 分子量: 99.1326
• InChiKey: MFXUSQSDQJBLBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-cyclobutylformamide 在 喹啉 、 对甲苯磺酰氯 作用下， 生成 异氰基环丁烷
  参考文献：
  名称：

  The Isonitrile—Nitrile Isomerization¹

  摘要：

  DOI：

  10.1021/jo01349a003
• 作为产物：
  描述：

  环丁基胺 、 甲酸乙酯 在 Novozyme 435 CALB 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到N-cyclobutylformamide
  参考文献：
  名称：

  使用甲酸乙酯对胺进行生物催化N-甲酰化的首次报道

  摘要：

  使用甲酸乙酯作为甲酰化剂，已经开发了不同胺的生物催化的N-甲酰化反应。该协议提供了一种轻而易举的策略，具有反应条件温和，疗效高，...

  DOI：

  10.1039/c6cc07679c

文献信息

• Inhibition of Human Alcohol Dehydrogenases by Formamides
  作者：John F. Schindler、Kristine B. Berst、Bryce V. Plapp

  DOI：10.1021/jm9707380

  日期：1998.5.1

  saturating concentrations of alcohols. Molecular modeling led to the design and synthesis of a series of cyclic, linear, and disubstituted formamides. Evaluation of 23 compounds provided structure-function information and selective inhibitors for the enzymes, which have overlapping but differing substrate specificities. Monosubstituted formamides are good inhibitors of class I and II enzymes, and disubstituted

  人醇脱氢酶（HsADH）包含I类（α，β和γ），II类（pi）和IV类（sigma）酶。酶的选择性抑制剂可用于防止形成有毒产物的醇类代谢。甲酰胺是醛的非反应性类似物，并与酶-NADH复合物结合[Ramaswamy，S .; Scholze，M .；Plapp，BV Biochemistry 1997，36，3522-3527]。它们是针对各种浓度酒精的非竞争性抑制剂，即使在饱和浓度的酒精下，它们也有效。分子建模导致了一系列环状，线性和双取代甲酰胺的设计和合成。对23种化合物的评估提供了酶的结构功能信息和选择性抑制剂，这些酶具有重叠但不同的底物特异性。单取代甲酰胺是I和II类酶的良好抑制剂，而双取代甲酰胺对α酶具有选择性。在pH 7和25摄氏度下Ki值为0.33-0.74 microM的选择性抑制剂包括HsADHα的N-环戊基-N-环丁基甲酰胺，HsADH beta1的N-苄基甲酰胺，HsADH
• Selective .kappa.-Opioid Agonists: Synthesis and Structure-Activity Relationships of Piperidines Incorporating an Oxo-Containing Acyl Group
  作者：Giuseppe Giardina、Geoffrey D. Clarke、Giulio Dondio、Giuseppe Petrone、Massimo Sbacchi、Vittorio Vecchietti

  DOI：10.1021/jm00047a006

  日期：1994.10

  This study describes the synthesis and the structure-activity relationships (SARs) of the (S)-(-)-enantiomers of a novel class of 2-(aminomethyl)piperidine derivatives, using K-opioid binding affinity and antinociceptive potency as the indices of biological activity. Compounds incorporating the 1-tetralon-6-ylacetyl residue (30 and 34-45) demonstrated an in vivo antinociceptive activity greater than predicted on the basis of their kappa-binding affinities. In particular, (2S)-2-[(dimethylamino)methyl]-1-[(5,6,7,8-tetrahydro-5-oxo-2-naphthyl)acetyl]piperidine (34) was found to have a potency similar to spiradoline in animal models of antinociception after subcutaneous administration, with ED(50)s of 0.47 and 0.73 mu mol/kg in the mouse and in the rat abdominal constriction tests, respectively. Further in vivo studies in mice and/or rats revealed that compound 34, compared to other selective K-agonists, has a reduced propensity to cause a number of K-related side effects, including locomotor impairment/sedation and diuresis, at antinociceptive doses. For example, it has an ED(50) Of 26.5 mu mol/kg sc in the rat rotarod model, exhibiting a ratio of locomotor impairment/sedation vs analgesia of 36. Possible reasons for this differential activity and its clinical consequence are discussed.
• The Isonitrile—Nitrile Isomerization¹
  作者：Joseph Casanova、Newton D. Werner、Ronald E. Schuster

  DOI：10.1021/jo01349a003

  日期：1966.11
• First report on bio-catalytic N-formylation of amines using ethyl formate
  作者：Rupesh E. Patre、Sanjib Mal、Pankaj R. Nilkanth、Sujit K. Ghorai、Sudhindra H. Deshpande、Myriem El Qacemi、Tomas Smejkal、Sitaram Pal、Bhanu N. Manjunath

  DOI：10.1039/c6cc07679c

  日期：——

  A Bio-catalyzed N-formylation reaction of different amines has been developed using ethyl formate as formylating agent. This protocol provides a facile and convenient strategy featuring mild reaction condition, high efficacy,...

  使用甲酸乙酯作为甲酰化剂，已经开发了不同胺的生物催化的N-甲酰化反应。该协议提供了一种轻而易举的策略，具有反应条件温和，疗效高，...