3-戊酮,1,5-二(二甲氨基)-,二盐酸 | 102308-93-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-戊酮,1,5-二(二甲氨基)-,二盐酸
• 英文名称: 1,5-bis-dimethylamino-pentan-3-one; dihydrochloride
• 英文别名: 1,5-Bis-dimethylamino-pentan-3-on; Dihydrochlorid；1,5-Bis(dimethylamino)pentan-3-one;hydrochloride
• CAS: 102308-93-0
• 化学式: C₉H₂₀N₂O*2ClH
• 分子量: 245.192
• InChiKey: HGKHZDOMIOKVPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.88
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  23.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-戊酮,1,5-二(二甲氨基)-,二盐酸 以 乙醇 为溶剂， 反应 18.0h， 生成 {2-[3-(Diethoxy-phosphorylmethyl)-1H-indol-2-yl]-ethyl}-phosphonic acid diethyl ester
  参考文献：
  名称：

  γ,γ'-二膦酰基酮的首次合成及其在 Fischer 反应中的反应性

  摘要：

  报告了导致新的 n , n '-二膦酰基酮 2 和 2 ' 的两种合成方法。第一种方法涉及碱催化将亚磷酸二乙酯加成到二亚芳基酮中。第二个利用亚磷酸三乙酯和乙氧基二苯基膦与 g , g '-双(二甲氨基)酮盐酸盐的反应。与苯肼盐酸盐反应后，化合物 2 和 2' 得到相应的 2-（膦酰基乙基）3-（膦酰基甲基）吲哚 3 。所有获得的产物的结构均通过NMR( 1 H, 31 P, 13 C)和IR光谱证实。

  DOI：

  10.1080/10426500211716
• 作为产物：
  描述：

  聚合甲醛 、 盐酸二甲胺 、 丙酮 以 溶剂黄146 为溶剂， 反应 3.0h， 以31%的产率得到3-戊酮,1,5-二(二甲氨基)-,二盐酸
  参考文献：
  名称：

  Evaluation of some Mannich bases of cycloalkanones and related compounds for cytotoxic activity

  摘要：

  A number of Mannich bases of cycloalkanones and related quaternary ammonium compounds were prepared for cytotoxic evaluation in order to examine the theory that sequential release of alkylating agents produces increased bioactivity compared to related compounds containing only 1 potential alkylating site. Many of the compounds had significant activity against murine L1210 cells and various human tumours. Some correlations between structure and activity were noted but the biological data did not support the view that potential sequential liberation of cytotoxic species produced compounds with increased potency. The formation of various oximes and oxime benzoates as candidate prodrugs was achieved but in general these compounds were not cytotoxic at the concentrations utilized. This observation may be due to the fact that the oximes were much more stable in deuterated phosphate buffered saline over a period of 48 h at 37-degrees-C than the Mannich bases, as revealed by H-1-NMR spectroscopy.

  DOI：

  10.1016/0223-5234(93)90148-8

文献信息

• Convenient First Synthesis of Hydroxy- and Amino-γ,γ′-bisphosphonates via Reduction and Reductive Amination of γ,γ′-Diphosphonyl Ketones
  作者：Ali Samarat、Marwa Yahyaoui、Iyadh Aouani、Soufiane Touil

  DOI：10.1246/cl.130160

  日期：2013.7.5

  Simple and efficient methodologies have been developed for the synthesis of novel hydroxy- and aminobisphosphonate derivatives, through the reduction and reductive amination of γ,γ′-diphosphonyl ke...

  通过γ,γ'-二膦酰基基团的还原和还原胺化，已经开发了用于合成新型羟基和氨基双膦酸酯衍生物的简单有效的方法。
• Notes: Products Obtained from Acetone, 1-Dimethylamino-3-pentanone and Diethyl Acetonedicarboxylate in the Mannich Reaction
  作者：F Blicke、F McCarty

  DOI：10.1021/jo01091a630

  日期：1959.9
• First Synthesis of γ,γ′-Diphosphonylketones and Their Reactivity in the Fischer Reaction
  作者：Soufiane Touil、Hedi Zantour

  DOI：10.1080/10426500211716

  日期：2002.5.1

  Two synthetic methods leading to the new n , n '-diphosphonylketones 2 and 2 ' are reported. The first method involves the base-catalyzed addition of diethylphosphite to diarylideneketones. The second one utilizes the reaction of triethylphosphite and ethoxydiphenylphosphine with g , g '-bis(dimethylamino)ketone hydrochlorides. On reaction with phenylhydrazine hydrochloride, compounds 2 and 2 ' give

  报告了导致新的 n , n '-二膦酰基酮 2 和 2 ' 的两种合成方法。第一种方法涉及碱催化将亚磷酸二乙酯加成到二亚芳基酮中。第二个利用亚磷酸三乙酯和乙氧基二苯基膦与 g , g '-双(二甲氨基)酮盐酸盐的反应。与苯肼盐酸盐反应后，化合物 2 和 2' 得到相应的 2-（膦酰基乙基）3-（膦酰基甲基）吲哚 3 。所有获得的产物的结构均通过NMR( 1 H, 31 P, 13 C)和IR光谱证实。
• Evaluation of some Mannich bases of cycloalkanones and related compounds for cytotoxic activity
  作者：JR Dimmock、KK Sidhu、M Chen、RS Reid、TM Allen、GY Kao、GA Truitt

  DOI：10.1016/0223-5234(93)90148-8

  日期：1993.1

  A number of Mannich bases of cycloalkanones and related quaternary ammonium compounds were prepared for cytotoxic evaluation in order to examine the theory that sequential release of alkylating agents produces increased bioactivity compared to related compounds containing only 1 potential alkylating site. Many of the compounds had significant activity against murine L1210 cells and various human tumours. Some correlations between structure and activity were noted but the biological data did not support the view that potential sequential liberation of cytotoxic species produced compounds with increased potency. The formation of various oximes and oxime benzoates as candidate prodrugs was achieved but in general these compounds were not cytotoxic at the concentrations utilized. This observation may be due to the fact that the oximes were much more stable in deuterated phosphate buffered saline over a period of 48 h at 37-degrees-C than the Mannich bases, as revealed by H-1-NMR spectroscopy.