N,N'-(1,4-dimethyl-butanediyl)-bis-benzamide | 178180-88-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N'-(1,4-dimethyl-butanediyl)-bis-benzamide
• 英文别名: N,N'-(1,4-Dimethyl-butandiyl)-bis-benzamid
• CAS: 178180-88-6
• 化学式: C₂₀H₂₄N₂O₂
• 分子量: 324.423
• InChiKey: NANJEJBWXMNXME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.2
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2,5-二氨基己烷 在 sodium carbonate 作用下， 以 水 为溶剂， 反应 1.0h， 生成 N,N'-(1,4-dimethyl-butanediyl)-bis-benzamide
  参考文献：
  名称：

  Inhibition of ornithine decarboxylase by the isomers of 1,4-dimethylputrescine

  摘要：

  1,4-Dimethylputrescine (2,5-hexanediamine) was separated into its racemic and meso isomers by fractional crystallization of its dibenzoyl derivative. The racemic form was resolved into its (+)- and (-)-isomers with (+)- and (-)-dibenzoyltartaric acids. None of the three isomers (meso, +, and -) inhibited ornithine decarboxylase (ODC) activity in vitro, while all the three were strongly inhibitory of ODC when assayed in vivo in rats or in H-35 hepatoma cells. In rat liver the three isomers also decreased the putrescine pool while only the (+)-isomer decreased spermidine content. In the H-35 cells the (-)- and (+)-isomers decreased the spermidine and spermine content. When ODC was induced in the latter by insulin it was found that the (-)-isomer strongly inhibited protein and ODC synthesis, while the (+)-isomer and the meso isomer were less inhibitory. The meso isomer was a good inducer of ODC antizyme in rat liver, while the (+)- and (-)-isomers were poor inducers of the former.

  DOI：

  10.1021/jm00169a025

文献信息

• Aziridines. 69. Reactions of N-Acylaziridines with Sodium Metal and Sodium Naphthalenide. Elimination of olefines
  作者：Pen-Yuan Lin、Konstantinos Bellos、J�rgen Werry、Petros Assithianakis、Rainer Wei�、Thomas Mall、Gunther Bentz、H. Stamm

  DOI：10.1002/prac.19963380153

  日期：——

  Reactions of N-acylaziridines 1a-g (N-benzoyl except 1d) with sodium or naphthalenide N-.- in THF provide a variety of products that usually arise via the aziridino ketyls 2. Homolytic ring opening of 2 generates the amidatoalkyl radicals 3. Only with a very short reaction time were small amounts of benzil or benzoylnaphthalenes obtained indicating a reversible trapping of 2 by dimerization or coupling with N-.-. Homolysis of 2 produced always the more stable 3 apart from reactions of monomethylaziridines 1c,d where the primary radical i-3c,d is kinetically favoured. The amides R(1)CONHCHR(4)CHR(2)R(3) (9: isopropylamides i-9c,d from 1c,d) were usually the main products. 9 arise from 3 either by H atom abstraction from THF (probably in sodium metal runs) or by reduction of 3 to carbanions 5 that abstract a proton from THF (N-.- runs). Addition of 5a (R(2-4) = H) to 1a gives finally the ketone 8a. Self reaction of primary radical 3a is dimerization. Self reaction of tertiary or secondary radicals is disproportionation when an allylamide arises. This isomerizes to an enamide unless it is conjugated.R(2)R(3)C=CHR(4) and R(1)CONH(2) arise (probably) always. The mechanism, possibly a cyclic process of anion 6, is not clear.
• Guenter; Tafel, Chemische Berichte, 1895, vol. 28, p. 380
  作者：Guenter、Tafel

  DOI：——

  日期：——