2-(1-hexamethyleneimino)acetophenone | 111733-88-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1-hexamethyleneimino)acetophenone
• 英文别名: 2-hexahydroazepin-1-yl-1-phenyl-ethanone；2-Hexahydroazepin-1-yl-1-phenyl-aethanon；2-(Azepan-1-yl)-1-phenylethanone
• CAS: 111733-88-1
• 化学式: C₁₄H₁₉NO
• mdl: MFCD00495884
• 分子量: 217.311
• InChiKey: QRYNIYTZIMWGTP-UHFFFAOYSA-N

物化性质

• 沸点：
  335.7±25.0 °C(Predicted)
• 密度：
  1.023±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1-hexamethyleneimino)acetophenone 在 高氯酸 、 Hg(II)-EDTA 作用下， 以 乙醇 为溶剂， 生成 4,6,7,8,9,10-Hexahydro-1-methyl-3-phenyl-azepino<2,1-c><1,2,4>triaziniumperchlorat
  参考文献：
  名称：

  甲基腙在胺脱氢中作为相邻基团

  摘要：

  具有环胺含量的 α-氨基酮的甲基腙与汞 (II) EDTA 产生相应的内酰胺，具有 4- 电子撤回和相邻基团参与。当暴露于高氯酸时，它们可以环化为 1,2,4-三嗪盐或水解为酮内酰胺。

  DOI：

  10.1002/ardp.19873200313
• 作为产物：
  描述：

  环己亚胺 、 alpha-氯乙酰苯 在 potassium iodide 作用下， 以 乙二醇 、 甲苯 为溶剂， 反应 12.0h， 生成 2-(1-hexamethyleneimino)acetophenone
  参考文献：
  名称：

  Hypolipidemic effects of α, β, and γ-alkylaminophenone analogs in rodents

  摘要：

  A number of N-substituted beta-alkylaminophenone derivatives including two alpha- and two gamma-alkylaminophenone analogs were synthesized and investigated for hypolipidemic activity in mice at 8 mg/kg/day ip. Most of these analogs were found to be significantly more active than lovastatin and clofibrate. N-Phenylpiperazinopropiophenone 16 was one of the best derivatives, lowering serum cholesterol levels 41% and serum triglyceride levels 48% after 16 days of drug administration in CF1 mice. In Sprague-Dawley rats, N-phenylpiperazinopropiophenone at 8 mg/kg/day orally also demonstrated more potent hypolipidemic activity than clofibrate, gemfibrozil, and lovastatin at their therapeutic dosage. It significantly reduced tissue cholesterol and triglyceride levels in the aorta wall tissue and lowered the cholesterol and triglyceride levels in chylomicron, very low density lipid (VLDL) and low density lipid (LDL) fractions, while it significantly elevated the cholesterol levels in high density lipid (HDL) fraction. This compound also proved to be active in lowering both cholesterol and triglyceride levels in hyperlipidemic mice and rats induced with atherogenic diet. In vitro liver acetyl coenzyme A (CoA) synthetase, 3-hydroxy-3-methyl glutaryl (HMG) CoA reductase, acyl CoA cholesterol acyl transferase (ACAT), sn-glycerol-3-phosphate acyltransferase, phosphatidylate phosphohydrolase, and hepatic lipoprotein lipase activities were significantly inhibited by N-phenylpiperazinopropiophenone from 25 to 100 mu M.

  DOI：

  10.1016/0223-5234(96)80365-5

文献信息

• Regioselective synthesis of piperidinones by metal-catalyzed ring expansion-carbonylation reactions. Remarkable cobalt and/or ruthenium carbonyl catalyzed rearrangement and cyclization reactions
  作者：Ming De Wang、Howard Alper

  DOI：10.1021/ja00044a010

  日期：1992.8

  Carbonylation of pyrrolidines, catalyzed by cobalt carbonyl, results in the formation of piperidinones. The reaction is regiospecific in most cases, and the yield of product is increased when ruthenium carbonyl is present as a second catalyst. The dual catalytic system [Co 2 (CO) 8 /Ru 3 (CO) 12 ] is useful for the novel rearrangement of heterocyclic nitrogen ketones ((CH 2 ) n NCH 2 COR, n=4-7] to

  由羰基钴催化的吡咯烷的羰基化导致哌啶酮的形成。在大多数情况下，该反应是区域特异性的，当羰基钌作为第二催化剂存在时，产物的产率会增加。双催化体系 [Co 2 (CO) 8 /Ru 3 (CO) 12 ] 可用于杂环氮酮 ((CH 2 ) n NCH 2 COR, n=4-7] 在 72- 93% 的产率。2,6-二甲基哌啶基酮的一种不寻常的金属催化环化反应以 86-94% 的产率提供了 5,6,7,8-四氢茚茚
• Boranes in synthesis. 2. Asymmetric synthesis of β-amino alcohols. A facile conversion of 2-amino acetophenones to the corresponding β-amino alcohols in high enantiomeric purity
  作者：David A. Beardsley、Gary B. Fisher、Christian T. Goralski、Lawrence W. Nicholson、Bakthan Singaram

  DOI：10.1016/s0040-4039(00)76745-1

  日期：1994.3

  The asymmetric reduction of 2-amino acetophenones with Ipc2BH or Ipc2BCl at −78°C, yields the corresponding β-amino alcohols in good to excellent yields. Although only modest (12–45% ee) enantiomeric excesses were obtained with Ipc2BH, 75–99% enantiomeric excesses were obtained when Ipc2BCl was used as the asymmetric reducing agent.

  在-78°C下用Ipc 2 BH或Ipc 2 BCl不对称还原2-氨基苯乙酮，可生成相应的β-氨基醇，收率为好至极好。尽管使用Ipc 2 BH仅获得了适度的对映体过量（12-45％ee），但是当使用Ipc 2 BCl作为不对称还原剂时，却获得了75-99％的对映体过量。
• Kondensierte Dihydro-1,2,4-triazine
  作者：Hans Möhrle、Peter Schillings

  DOI：10.1002/ardp.19873200303

  日期：——

  Hydrazone von α‐Aminoketonen mit cyclischem Aminanteil ergeben mit Quecksilber (II)‐EDTA eine Cyclodehydrierung zu entspr. kondensierten Dihydrotriazinen.

  含有环胺的 α-氨基酮的腙与汞 (II) EDTA 发生环化脱氢反应，得到相应的缩合二氢三嗪。
• Blicke; Johnson, Journal of the American Pharmaceutical Association (1912), 1956, vol. 45, p. 440
  作者：Blicke、Johnson

  DOI：——

  日期：——
• Beardsley David A., Fisher Gary B., Goralski Christian T., Nicholson Lawr+, Tetrahedron Lett, 35 (1994) N 10, S 1511-1514
  作者：Beardsley David A., Fisher Gary B., Goralski Christian T., Nicholson Lawr+

  DOI：——

  日期：——