N-(正丁基)-b-氨基丙酸乙酯 | 10494-81-2

• 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
• 中文名称: N-(正丁基)-b-氨基丙酸乙酯
• 英文名称: ethyl 3-butylaminopropionate
• 英文别名: ethyl 3-n-butylaminopropionate；ethyl 3-(butylamino)propanoate；ethyl N-(n-butyl)-b-aminopropionate
• CAS: 10494-81-2
• 化学式: C₉H₁₉NO₂
• mdl: MFCD01100549
• 分子量: 173.255
• InChiKey: HTFPNDKVPVWBDL-UHFFFAOYSA-N

物化性质

• 沸点：
  65 °C(Press: 1.4 Torr)
• 密度：
  0.912 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.888
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(正丁基)-b-氨基丙酸乙酯 在 盐酸 、 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 40.17h， 生成 1-butyl-5-chloro-4-[1-methoxymeth-(E)-ylidene]-7-methyl-1,2,3,4-tetrahydro[1,6]naphthyridine
  参考文献：
  名称：

  Potent, Orally Active Corticotropin-Releasing Factor Receptor-1 Antagonists Containing a Tricyclic Pyrrolopyridine or Pyrazolopyridine Core

  摘要：

  Two new classes of tricyclic-based corticotropin-releasing factor (CRF1) receptor-1 antagonists were designed by constraining known 1H-pyrrolo[2,3-b]pyridine and 1H-pyrazolo[3,4-b]pyridine ligands. Pyrrole- and pyrazole-based molecules 19g and 22a, respectively, were discovered that potently bind the recombinant CRF1 receptor (K-i = 3.5, 2.9 nM) and inhibit adrenocorticotropic hormone (ACTH) release from rat pituitary cell culture (IC50 = 14, 6.8 nM). These compounds show good oral bioavailabity (F = 24%, 7.0%) and serum half-lives in rats (t(1/2) = 6.3, 12 h) and penetrate the rat brain ([brain]/[plasma] = 0.27, 0.52) but tend toward large volumes of distribution (V-D = 38, 44 L kg(-1)) and rapid clearances (CL = 70, 43 mL min(-1) kg(-1)). When given orally, both the pyrazole and the pyrrole leads dose-dependently inhibit stress-induced ACTH release in vivo. ACTH reductions of 84-86% were observed for 30 mg kg(-1) doses.

  DOI：

  10.1021/jm050070m
• 作为产物：
  描述：

  正丁胺 、 丙烯酸乙酯 在 ruthenium trichloride poly(ethylene glycol) 2000 作用下， 反应 8.0h， 以96%的产率得到N-(正丁基)-b-氨基丙酸乙酯
  参考文献：
  名称：

  聚（乙二醇）中的 RuCl3：用于氮和硫亲核试剂共轭加成的高效且可回收的催化剂

  摘要：

  在聚乙二醇 (PEG) 中催化量 (0.5 mol%) 的 RuCl 3 介导的伯胺、仲胺和芳香胺、硫醇和氨基甲酸酯与 α,β-不饱和化合物的 1,4-共轭加成提供了以高产率获得所需的β-取代羰基。特别是，我们发现脂肪族伯胺和芳香族伯胺与 RuCl 3 -PEG 以非常高的产率产生单一的加合物作为唯一的产物。RuCl 3 -PEG 很容易通过溶剂沉淀进行回收，具有高效的可回收性，高产率证明了这一点。其对水分和氧气的低敏感性、对不同官能团的高耐受性和高效的可回收性使RuCl 3 -PEG适用于实验室和工业规模的β-取代羰基化合物的合成。

  DOI：

  10.1055/s-2005-870010

文献信息

• Cesium fluoride catalyzed Aza-Michael addition reaction in aqueous media
  作者：Vilas B. Labade、Shivaji S. Pawar、Murlidhar S. Shingare

  DOI：10.1007/s00706-011-0550-2

  日期：2011.10

  green approach to the Aza-Michael addition reaction between an amine and α,β-unsaturated compounds has been achieved by conventional as well as non-conventional methods. The reaction is catalyzed by cesium fluoride (CsF) in aqueous media at ambient temperature to afford the product in excellent yield. Ultrasound irradiation has been used as a non-conventional energy source, which reduces the reaction

  摘要胺与α，β-不饱和化合物之间的Aza-Michael加成反应的绿色方法已经通过常规方法和非常规方法实现。在室温下，在水介质中，氟化铯（CsF）催化该反应，从而以优异的产率提供产物。超声辐射已被用作非常规能源，从而缩短了反应时间并提高了产品收率。 图形概要
• Aza-Michael Mono-addition Using Acidic Alumina under Solventless Conditions
  作者：Giovanna Bosica、Roderick Abdilla

  DOI：10.3390/molecules21060815

  日期：——

  Aza-Michael reactions between primary aliphatic and aromatic amines and various Michael acceptors have been performed under environmentally-friendly solventless conditions using acidic alumina as a heterogeneous catalyst to selectively obtain the corresponding mono-adducts in high yields. Ethyl acrylate was the main acceptor used, although others such as acrylonitrile, methyl acrylate and acrylamide

  脂肪族和芳香族伯胺与各种迈克尔受体之间的 Aza-Michael 反应在环境友好的无溶剂条件下使用酸性氧化铝作为非均相催化剂进行，以高产率选择性地获得相应的单加合物。丙烯酸乙酯是主要使用的受体，但其他如丙烯腈、丙烯酸甲酯和丙烯酰胺也被成功利用。双官能胺也以良好到极好的产率得到单加合物。此类化合物可作为合成抗癌和抗生素药物的中间体。
• Pyrroloazepine derivatives
  申请人：Suntory Limited

  公开号：US05206239A1

  公开（公告）日：1993-04-27

  Disclosed herein are pyrroloazepine derivatives, which are useful as therapeutics for circulatory diseases, represented by the following formula (I): ##STR1## wherein R means a hydrogen atom, a linear or branched C.sub.1-6 alkyl group or a C.sub.7-10 aralkyl group, A denotes a linear or branched C.sub.2-10 alkylene, alkenylene or alkynylene group, Z stands for O, NOR.sub.1 or NOCOR.sub.5 in which R.sub.1 and R.sub.5 is a hydrogen atom or an alkyl, aryl or aralkyl group, and Y means a particular piperidinyl or pyrrolidinyl group; and salts thereof. Their preparation processes are also disclosed.

  本文披露了一种吡咯环庚烯衍生物，可用作治疗循环系统疾病的药物，其化学式如下（I）：其中R代表氢原子、直链或支链C.sub.1-6烷基或C.sub.7-10芳基烷基，A代表直链或支链C.sub.2-10烷基、烯烃基或炔烃基，Z代表O、NOR.sub.1或NOCOR.sub.5，其中R.sub.1和R.sub.5为氢原子或烷基、芳基或芳基烷基，Y代表特定的哌啶基或吡咯基；以及其盐。同时也披露了它们的制备过程。
• Synthesis and Pharmacological Evaluation of Pyrroloazepine Derivatives as Potent Antihypertensive Agents with Antiplatelet Aggregation Activity.
  作者：Akira MIZUNO、Norio INOMATA、Mikiko MIYA、Tomoe KAMEI、Makoto SHIBATA、Toshio TATSUOKA、Maki YOSHIDA、Chikako TAKIGUCHI、Tomoko MIYAZAKI

  DOI：10.1248/cpb.47.246

  日期：——

  A series of 1-aminoalkyl-pyrrolo[2, 3-c]azepin-8-one derivatives was synthesized and evaluated as α1 adrenergic and serotonin 2 (5-HT2) receptor antagonists, with the aim of finding a novel antihypertensive agent potently exhibiting both activities. Some compounds with a 4-[4-(4-fluorobenzoyl)piperidino]butyl group at the 1-position exhibited both activities, and varied significantly in terms of the substituents at the 4-position of the pyrroloazepine ring. Among the compounds obtained in this study, (E)-1-[4-[4-(4-fluorobenzoyl)piperidino]butyl]-4-hydroxyimino-7-methyl-1, 4, 5, 6, 7, 8-hexahydropyrrolo[2, 3-c]azepin-8-one (15a, SUN9221) displayed potent α1-adrenergic antagonistic activity (pA2=8.89±0.21) and 5-HT2 antagonistic activity (pA2=8.74±0.22) in isolated guinea pig arteries. This compound exhibited antihypertensive activity and a duration of action equivalent to orally administered prazosin or doxazosin, 3 mg/kg, in conscious spontaneously hypertensive rats, as well as potent antiplatelet aggregation activity.

  合成了一系列1-氨基烷基吡咯并[2, 3-c]氮杂环辛酮衍生物，并评估其作为α1肾上腺素能和血清素2（5-HT2）受体拮抗剂的活性，旨在寻找一种新型的具有强效双重活性的抗高血压药物。部分在1位具有4-[4-(4-氟苯甲酰基)piperidino]丁基基团的化合物显示了双重活性，并在吡咯氮杂环的4位取代基方面表现出显著差异。在本研究中获得的化合物中，（E）-1-[4-[4-(4-氟苯甲酰基)piperidino]丁基]-4-羟基亚胺-7-甲基-1, 4, 5, 6, 7, 8-六氢吡咯并[2, 3-c]氮杂环辛酮（15a，SUN9221）在离体豚鼠动脉中表现出强效的α1-肾上腺素能拮抗活性（pA2=8.89±0.21）和5-HT2拮抗活性（pA2=8.74±0.22）。这一化合物表现出抗高血压活性，其作用持续时间相当于口服给药的哌唑嗪或多沙唑嗪（3 mg/kg）在清醒自发性高血压大鼠中的效果，同时还具有强效的抗血小板聚集活性。
• 化合物、化合物产品及制备方法和用途
  申请人：中国人民解放军军事科学院军事医学研究院

  公开号：CN113461559B

  公开（公告）日：2023-08-08

  本发明公开了化合物、化合物产品及制备方法和用途。所述化合物具有如式1所示的结构通式，其中，R1为烷基；所述化合物产品，包含式1所述的化合物。所述化合物和化合物产品可用于驱避昆虫，且驱避效果好。