N-butylquinolin-2-amine | 91821-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-butylquinolin-2-amine
• 英文别名: N-Butyl-N-quinolin-2-ylamine
• CAS: 91821-02-2
• 化学式: C₁₃H₁₆N₂
• mdl: MFCD11123472
• 分子量: 200.283
• InChiKey: OECWVHLMORFOCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氯喹啉 、 正丁胺 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 以31%的产率得到N-butylquinolin-2-amine
  参考文献：
  名称：

  Inhibitors of protein isoprenyl transferases

  摘要：

  具有以下结构式或其药用可接受盐的化合物，其中R1为(a)氢，(b)较低烷基，(c)烯基，(d)烷氧基，(e)硫代烷氧基，(f)卤素，(g)卤代烷基，(h)芳基-L2—，和(i)杂环-L2—；R2选自(a) (b) —C(O)NH—CH(R14)—C(O)OR15，(d) —C(O)NH—CH(R14)—C(O)NHSO2R16，(e) —C(O)NH—CH(R14)-四唑基，(f) —C(O)NH-杂环，和(g) —C(O)NH—CH(R14)—C(O)NR17R18；R3为取代或未取代的杂环或芳基，取代或未取代的环烷基或环烯基，以及—P(W)RR3RR3′；R4为氢，较低烷基，卤代烷基，卤素，芳基，芳基烷基，杂环，或(杂环)烷基；L1为空缺或选自(a) —L4—N(R5)—L5—，(b) —L4—O—L5—，(c) —L4—S(O)n—L5—，(d) —L4—L6—C(W)—N(R5)—L5—，(e) —L4—L6—S(O)m—N(R5)—L5—，(f) —L4—N(R5)—C(W)—L7—L5—，(g) —L4—N(R5)—S(O)p—L7—L5—，(h)可选择取代的烷基，(i)可选择取代的烯基，(j)可选择取代的炔基，(k)共价键，(l)和(m)是蛋白异戊二烯基转移酶的抑制剂。还公开了蛋白异戊二烯基转移酶抑制剂组合物和抑制蛋白异戊二烯基转移酶的方法。

  公开号：

  US06310095B1

文献信息

• Inhibitors of protein isoprenyl transferases
  申请人：University of Pittsburgh

  公开号：US06310095B1

  公开（公告）日：2001-10-30

  Compounds having the formula or a pharmaceutically acceptable salt thereof wherein R1 is (a) hydrogen, (b) loweralkyl, (c) alkenyl, (d) alkoxy, (e) thioalkoxy, (f) halo, (g) haloalkyl, (h) aryl-L2—, and (i) heterocyclic-L2—; R2 is selected from (a) (b) —C(O)NH—CH(R14)—C(O)OR15, (d) —C(O)NH—CH(R14)—C(O)NHSO2R16, (e) —C(O)NH—CH(R14)-tetrazolyl, (f) —C(O)NH-heterocyclic, and (g) —C(O)NH—CH(R14)—C(O)NR17R18; R3 is substituted or unsubstituted heterocyclic or aryl, substituted or unsubstituted cycloalkyl or cycloalkenyl, and —P(W)RR3RR3′; R4 is hydrogen, lower alkyl, haloalkyl, halogen, aryl, arylakyl, heterocyclic, or (heterocyclic)alkyl; L1 is absent or is selected from (a) —L4—N(R5)—L5—, (b) —L4—O—L5—, (c) —L4—S(O)n—L5— (d) —L4—L6—C(W)—N(R5)—L5—, (e) —L4—L6—S(O)m—N(R5)—L5 —, (f) —L4—N(R5)—C(W)—L7—L5—, (g) —L4—N(R5)—S(O)p—L7—L5—, (h) optionally substituted alkylene, (i) optionally substituted alkenylene, (j) optionally substituted alkynylene (k) a covalent bond, (l) and (m) are inhibitors of protein isoprenyl transferases. Also disclosed are protein isoprenyl transferase inhibiting compositions and a method of inhibiting protein isoprenyl transferases.

  具有以下结构式或其药用可接受盐的化合物，其中R1为(a)氢，(b)较低烷基，(c)烯基，(d)烷氧基，(e)硫代烷氧基，(f)卤素，(g)卤代烷基，(h)芳基-L2—，和(i)杂环-L2—；R2选自(a) (b) —C(O)NH—CH(R14)—C(O)OR15，(d) —C(O)NH—CH(R14)—C(O)NHSO2R16，(e) —C(O)NH—CH(R14)-四唑基，(f) —C(O)NH-杂环，和(g) —C(O)NH—CH(R14)—C(O)NR17R18；R3为取代或未取代的杂环或芳基，取代或未取代的环烷基或环烯基，以及—P(W)RR3RR3′；R4为氢，较低烷基，卤代烷基，卤素，芳基，芳基烷基，杂环，或(杂环)烷基；L1为空缺或选自(a) —L4—N(R5)—L5—，(b) —L4—O—L5—，(c) —L4—S(O)n—L5—，(d) —L4—L6—C(W)—N(R5)—L5—，(e) —L4—L6—S(O)m—N(R5)—L5—，(f) —L4—N(R5)—C(W)—L7—L5—，(g) —L4—N(R5)—S(O)p—L7—L5—，(h)可选择取代的烷基，(i)可选择取代的烯基，(j)可选择取代的炔基，(k)共价键，(l)和(m)是蛋白异戊二烯基转移酶的抑制剂。还公开了蛋白异戊二烯基转移酶抑制剂组合物和抑制蛋白异戊二烯基转移酶的方法。
• A mild and metal-free synthesis of 2- and 1-alkyl/aryl/dialkyl-aminoquinolines and isoquinolines
  作者：Yerramsetti Nanaji、Seema Kirar、Sandip V. Pawar、Ashok Kumar Yadav

  DOI：10.1039/c9ra10397j

  日期：——

  A simple synthetic strategy has been developed for the synthesis of 2- and 1-alkyl/aryl/dialkylaminoquinolines and isoquinolines from the easily available quinoline and isoquinoline-N-oxides, different amines, triflic anhydride as activating agent and acetonitrile as solvent in a one-pot reaction under metal-free conditions at 0 °C to room temperature.

  开发了一种简单的合成策略，用于从容易获得的喹啉和异喹啉-N-氧化物、不同的胺、作为活化剂的三氟甲磺酸酐和作为溶剂的乙腈中合成2-和1-烷基/芳基/二烷基氨基喹啉和异喹啉。 -0℃至室温下无金属条件下的罐式反应。
• Cyclopentapyridine and tetrahydroquinoline derivatives
  申请人：Lefker A. Bruce

  公开号：US20060247254A1

  公开（公告）日：2006-11-02

  6,7-Dihydro-5H-cyclopenta[b]pyridine and 5,6,7,8-tetrahydroquinoline compounds of Formula (I), including salts, hydrates and solvates thereof, that act as 5-HT 2 receptor ligands and their uses in the treatment of diseases linked to the activation of 5-HT 2c receptors are described herein.

  本文介绍了公式(I)中的6,7-二氢-5H-环戊[b]吡啶和5,6,7,8-四氢喹啉化合物，包括其盐、水合物和溶剂化物，它们作为5-HT2受体配体，并且它们在治疗与5-HT2受体激活有关的疾病方面的用途。
• Phosphonium Salt-Promoted C2–H Functionalization of Heterocyclic <i>N</i>-Oxides
  作者：Qian Ma、Yuze Shi、Dong Wang

  DOI：10.1021/acs.orglett.3c03742

  日期：2023.12.29

  We report the development of a phosphonium salt as a remarkable activating agent that enables the direct conversion of C2–H bonds of a variety of heterocyclic N-oxides into C2–N, C2–O, or C2–S bonds with high efficiency. The phosphonium salt was prepared on a >150 g scale in a single step and is tolerant of multiple functionalities.

  我们报告了鏻盐作为一种卓越的活化剂的发展，它能够将各种杂环N-氧化物的C2-H键直接高效地转化为C2-N、C2-O或C2-S键。鏻盐一步制备 >150 g 规模，并且具有多种功能。
• Green and fast 2-aryloxylation/amination of quinolines
  作者：Changna Bu、Kaijuan Wang、Chengcheng Gong、Dong Wang

  DOI：10.1039/d3gc05178a

  日期：——

  activating agent-promoted deoxygenative aryloxylation/amination. The main challenges in constructing C2–O or C2–N bonds from N-oxides lie in overcoming two side reactions: the reaction between the activating agent and the nucleophile, and the associated reaction at the C4-position. Compared to previous reports, this method benefits from an eco-friendly solvent, short reaction time, simple operation, and wide

  通过活化剂促进的脱氧芳氧基化/胺化，分别开发了2-芳氧基喹啉和2-氨基喹啉的快速、高效和环保的合成方法。从N-氧化物构建C2-O或C2-N键的主要挑战在于克服两个副反应：活化剂和亲核试剂之间的反应，以及C4位的相关反应。与之前的报道相比，该方法具有溶剂环保、反应时间短、操作简单、底物范围广等优点，可提供多种杂芳基醚和胺。我们展示了克级合成并计算了绿色化学指标，以突出所开发的合成方法的优势。