N-butylpentan-3-imine | 19306-78-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-butylpentan-3-imine
• 英文别名: N-(1-Ethylpropylidene)-n-butylamine；3-Butylimino-pentan；(1-ethyl-propylidene)-butyl-amine；(1-Aethyl-propyliden)-butyl-amin；Pentan-3-on-butylimin；1-Butanamine, N-(1-ethylpropylidene)-
• CAS: 19306-78-6
• 化学式: C₉H₁₉N
• 分子量: 141.257
• InChiKey: HPGDDLOEFSSBJX-UHFFFAOYSA-N

物化性质

• 沸点：
  64 °C(Press: 16 Torr)
• 密度：
  0.78±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-butylpentan-3-imine 在 氯化亚砜 、 水 、 N,N-二甲基甲酰胺 、 sodium hydroxide 作用下， 以 乙醇 、 二乙二醇二甲醚 、 甲苯 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Selective CB2 agonists with anti-pruritic activity: Discovery of potent and orally available bicyclic 2-pyridones

  摘要：

  The CB2 receptor has emerged as a potential target for the treatment of pruritus as well as pain without CB1-mediated side effects. We previously identified 2-pyridone derivatives 1 and 2 as potent CB2 agonists; however, this series of compounds was found to have unacceptable pharmacokinetic profiles with no significant effect in vivo. To improve these profiles, we performed further structural optimization of 1 and 2, which led to the discovery of bicyclic 2-pyridone 18e with improved CB2 affinity and selectivity over CB1. In a mouse pruritus model, 18e inhibited compound 48/80 induced scratching behavior at a dose of 100 mg/kg. In addition, the docking model of 18e with an active-state CB2 homology model indicated the structural basis of its high affinity and selectivity over CB1. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.03.030
• 作为产物：
  描述：

  正丁胺 、 3-戊酮 以 甲苯 为溶剂， 反应 24.0h， 生成 N-butylpentan-3-imine
  参考文献：
  名称：

  Selective CB2 agonists with anti-pruritic activity: Discovery of potent and orally available bicyclic 2-pyridones

  摘要：

  The CB2 receptor has emerged as a potential target for the treatment of pruritus as well as pain without CB1-mediated side effects. We previously identified 2-pyridone derivatives 1 and 2 as potent CB2 agonists; however, this series of compounds was found to have unacceptable pharmacokinetic profiles with no significant effect in vivo. To improve these profiles, we performed further structural optimization of 1 and 2, which led to the discovery of bicyclic 2-pyridone 18e with improved CB2 affinity and selectivity over CB1. In a mouse pruritus model, 18e inhibited compound 48/80 induced scratching behavior at a dose of 100 mg/kg. In addition, the docking model of 18e with an active-state CB2 homology model indicated the structural basis of its high affinity and selectivity over CB1. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.03.030

文献信息

• Synthesis of spiroisoindolinones by palladium-catalyzed heterocyclization of 2-iodobenzoyl chloride with ketimines
  作者：Chan Sik Cho、Xue Wu、Li Hong Jiang、Sang Chul Shim、Hong Rak Kim

  DOI：10.1002/jhet.5570360147

  日期：1999.1

  2-Iodobenzoyl chloride reacts with ketimines in acetonitrile at 100° under carbon monoxide pressure in the presence of a catalytic amount of a palladium catalyst together with triethylamine to afford the corresponding spiroisoindolinones in high yields.

  2-碘苯甲酰氯在催化量的钯催化剂和三乙胺的存在下，在一氧化碳压力下于100°C下与乙酮中的酮亚胺反应，以高收率得到相应的螺异吲哚满酮。
• Iridium-catalyzed aziridination of aliphatic aldehydes, aliphatic amines and ethyl diazoacetate
  作者：Takashi Kubo、Satoshi Sakaguchi、Yasutaka Ishii

  DOI：10.1039/b000518p

  日期：——

  Three-component coupling reactions of aliphatic aldehydes, aliphatic amines and ethyl diazoacetate to the corresponding aziridine derivatives has been achieved by the use of [Ir(cod)Cl]2 as a catalyst under mild conditions; for instance, the reaction of n-butyraldehyde, tert-butylamine and ethyl diazoacetate in the presence of a catalytic amount of [Ir(cod)Cl]2 in THF at −10 °C gave 1-tert-butyl-2-ethoxycarbonyl-3-propylaziridine in 85% yield in high stereoselectivity (cis : trans = 96∶4).

  通过使用[Ir(cod)Cl]2作为催化剂，在温和条件下实现了脂肪醛、脂肪胺和重氮乙酸乙酯的三组分耦合反应，生成相应的氮杂环丙烷衍生物；例如，在THF中，-10 °C下，在[Ir(cod)Cl]2的催化量存在下，正丁醛、叔丁胺和重氮乙酸乙酯的反应生成了1-叔丁基-2-乙氧羰基-3-丙基氮杂环丙烷，产率为85%，且具有高立体选择性（顺式：反式 = 96∶4）。
• Processes for the preparation of a carobxylic anhydride and use of the carboxylic anhydride as an acylation agent
  申请人：Drent Eit

  公开号：US20050059841A1

  公开（公告）日：2005-03-17

  A process for the preparation of an carboxylic anhydride by reaction of an ethylenically unsaturated compound with carbon monoxide and an carboxylic acid in the presence of a catalyst involving: a) a source of a group VIII metal; b) a bidentate diphosphine of formula I, wherein R 1 represents a bivalent radical that together with the phosphorus atom to which it is attached is an optionally substituted 2-phospha-tricyclo[3.3.1.1 3,7}]-decyl group or a derivative thereof in which one or more of the carbon atoms are replaced by heteroatoms (“2-PA” group); wherein R 2 and R 3 independently represent univalent radicals of up to 20 atoms or jointly form a bivalent radical of up to 20 atoms; and wherein R represents a bivalent organic bridging group; and, c) a complexing anion; wherein the complexing anion is the anion of the carboxylic acid. A process wherein the carboxylic acid is prepared in-situ and use of the carboxylic anhydride as an acylation agent.

  一种通过乙烯基不饱和化合物与一氧化碳和羧酸在催化剂存在下反应制备羧酸酐的工艺，涉及： a) 第 VIII 族金属源； b) 式 I 的二叉二膦、 其中 R 1 代表二价基，该二价基与所连接的磷原子一起是任选取代的 2-磷杂三环[3.3.1.13,7}]-癸基或其衍生物，其中一个或多个碳原子被杂原子取代（"2-PA "基）； 其中 R 2 和 R 3 独立地代表多达 20 个原子的单价基，或共同形成多达 20 个原子的二价基；其中 R 代表二价有机桥基；以及 c) 络合阴离子；其中络合阴离子是羧酸的阴离子。一种工艺，其中羧酸在原位制备，并使用羧酸酐作为酰化剂。
• SYNTHESIS AND PHYSIOLOGICAL ACTIVITIES OF NEW ACYCLIC AMINOPHOSPHONATES
  作者：J. S. Wieczorek、R. Gancarz、K. Bielecki、E. Grzyś、J. Sarapuk

  DOI：10.1080/10426500008076535

  日期：2000.1.1

  The dependence of biological activity of 37 newly synthesized acyclic aminomethanephosphonic acid derivatives on their structure was studied. It was found that the phytotoxicity of the compounds studied depended on their hydrophobic parameters, and in a smaller extent on the electronic parameters of the substituents on nitrogen and phosphorus atoms. No phytotoxicity dependence on the steric parameters of compounds was found. Tested organism was Spirodela oligorrhiza and the parameter studied was the concentration of compounds causing 50 % growth inhibition (EC50) The test had preliminary character and permitted to eliminate the less promising compounds out of further studies.
• Factors controlling regioselectivity in deprotonations of unsymmetrical ketimines
  作者：J. Kirk Smith、David E. Bergbreiter、Martin Newcomb

  DOI：10.1021/ja00351a045

  日期：1983.6