N-(4-Pyrrolidinocyclohex-3-enyl)acetamid | 102745-76-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-(4-Pyrrolidinocyclohex-3-enyl)acetamid
• 英文别名: 4-acetamido-1-pyrrolidinocyclohexene；N-(4-(Pyrrolidin-1-yl)cyclohex-3-en-1-yl)acetamide；N-(4-pyrrolidin-1-ylcyclohex-3-en-1-yl)acetamide
• CAS: 102745-76-6
• 化学式: C₁₂H₂₀N₂O
• 分子量: 208.304
• InChiKey: WSVGFFKZSAQHCC-UHFFFAOYSA-N

物化性质

• 熔点：
  150-158 °C
• 沸点：
  409.0±45.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-Pyrrolidinocyclohex-3-enyl)acetamid 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 氨 、 氢气 、 sodium acetate 、 sodium 、 sodium cyanoborohydride 、 一水合肼 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙二醇 、 溶剂黄146 为溶剂， -33.0~25.0 ℃ 、101.33 kPa 条件下， 反应 57.25h， 生成 6,7,8,9-tetrahydro-3H,10H-pyrrolo<3,2-a>carbazol-7-amine
  参考文献：
  名称：

  Ligand-receptor interactions via hydrogen-bond formation. Synthesis and pharmacological evaluation of pyrrolo and pyrido analogs of the cardiotonic agent 7-hydroxycyclindole

  摘要：

  The syntheses of N,N-dimethyl-6,7,8,9-tetrahydro-3H,10H-pyrrolo[3,2-a] carbazol-7-amine (8), N,N-dimethyl-7,8,9,10-tetrahydro-11H-pyrido[3,2-a] carbazol-8-amine (9a), and the N,N,11-trimethyl analogue (9b) are described. The in vitro inotropic activity of these compounds, as well as the known cardiotonics amrinone and 7-hydroxycyclindole (7), was investigated. Compound 8, a pyrrolo analogue of 7, was devoid of inotropic activity, while the pyrido analogues 9 were equiactive to 7 and amrinone. These results suggest that the hydroxyl group of 7 functions as an H-bond acceptor, rather than a donor, and that on interaction of 7, and the pyrido analogues 9, with a common receptor, an orbital occupied by one of the oxygen lone pair electrons of 7 must assume the same orientation as the orbital occupied by the pyridine nitrogen lone pair.

  DOI：

  10.1021/jm00158a022
• 作为产物：
  描述：

  对乙酰氨基酚 在 镍 sodium dichromate 、 硫酸 、 氢气 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 180.0 ℃ 、12.07 MPa 条件下， 反应 6.33h， 生成 N-(4-Pyrrolidinocyclohex-3-enyl)acetamid
  参考文献：
  名称：

  Ligand-receptor interactions via hydrogen-bond formation. Synthesis and pharmacological evaluation of pyrrolo and pyrido analogs of the cardiotonic agent 7-hydroxycyclindole

  摘要：

  The syntheses of N,N-dimethyl-6,7,8,9-tetrahydro-3H,10H-pyrrolo[3,2-a] carbazol-7-amine (8), N,N-dimethyl-7,8,9,10-tetrahydro-11H-pyrido[3,2-a] carbazol-8-amine (9a), and the N,N,11-trimethyl analogue (9b) are described. The in vitro inotropic activity of these compounds, as well as the known cardiotonics amrinone and 7-hydroxycyclindole (7), was investigated. Compound 8, a pyrrolo analogue of 7, was devoid of inotropic activity, while the pyrido analogues 9 were equiactive to 7 and amrinone. These results suggest that the hydroxyl group of 7 functions as an H-bond acceptor, rather than a donor, and that on interaction of 7, and the pyrido analogues 9, with a common receptor, an orbital occupied by one of the oxygen lone pair electrons of 7 must assume the same orientation as the orbital occupied by the pyridine nitrogen lone pair.

  DOI：

  10.1021/jm00158a022

文献信息

• Synthesis of Substituted Anilines from Cyclohexanones Using Pd/C–Ethylene System and Its Application to Indole Synthesis
  作者：Katsumi Maeda、Ryosuke Matsubara、Masahiko Hayashi

  DOI：10.1021/acs.orglett.0c04056

  日期：2021.3.5

  The synthesis of anilines and indoles from cyclohexanones using a Pd/C–ethylene system is reported. A simple combination of NH4OAc and K2CO3 under nonaerobic conditions was found to be the most suitable to perform this reaction. Hydrogen transfer between cyclohexanone and ethylene generates the desired products. The reaction tolerates a variety of substitutions on the starting cyclohexanones.

  据报道，使用Pd / C-乙烯系统可从环己酮合成苯胺和吲哚。发现在无氧条件下简单的NH 4 OAc和K 2 CO 3组合最适合进行该反应。环己酮和乙烯之间的氢转移产生了所需的产物。该反应可耐受起始环己酮上的各种取代。
• Teuber, Hans-Joachim; Tsaklakidis, Christos, Liebigs Annalen der Chemie, 1991, # 8, p. 835 - 837
  作者：Teuber, Hans-Joachim、Tsaklakidis, Christos

  DOI：——

  日期：——
• TEUBER, HANS-JOACHIM;TSAKLAKIDIS, CHRISTOS, LIEBIGS ANN. CHEM.,(1991) N, C. 835-837
  作者：TEUBER, HANS-JOACHIM、TSAKLAKIDIS, CHRISTOS

  DOI：——

  日期：——
• DIONNE G.; HUMBER L. G.; ASSELIN A.; MCQUILLAN J.; TREASURYWALA A. M., J. MED. CHEM., 29,(1986) N 8, 1452-1457
  作者：DIONNE G.、 HUMBER L. G.、 ASSELIN A.、 MCQUILLAN J.、 TREASURYWALA A. M.

  DOI：——

  日期：——
• Method for Fluoroalkylation of Enamines
  申请人：Arxada AG

  公开号：US20220204464A1

  公开（公告）日：2022-06-30

  The invention discloses a method for fluoroalkylation of enamines with a fluoro alkyl halide in the presence of a base.