N1-(2-(4-tosylpiperazin-1-yl)ethyl)ethane-1,2-diamine

• 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: N1-(2-(4-tosylpiperazin-1-yl)ethyl)ethane-1,2-diamine
• 英文别名: N'-[2-[4-(4-methylphenyl)sulfonylpiperazin-1-yl]ethyl]ethane-1,2-diamine
• 化学式: C₁₅H₂₆N₄O₂S
• 分子量: 326.463
• InChiKey: GEOPNIFGECBOHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  87
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  toluene sulfonyl chloride 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 生成 N1-(2-(4-tosylpiperazin-1-yl)ethyl)ethane-1,2-diamine
  参考文献：
  名称：

  One-Step Cyclization: Synthesis of N-Heteroalkyl-N′-tosylpiperazines

  摘要：

  Piperazine derivatives are important intermediates in organic synthesis and useful building blocks in pharmaceutical and fine chemical industries. Currently available synthetic routes for these heterocyclic compounds have limited scope owing to the harsh reaction conditions, low yields, and multistep process. Herein, we reported a practical method for synthesis of alkyl-, alcohol-, amine-, and ester-extended tosylpiperazines under mild conditions with moderate to high yields. This protocol exhibits potential applicability in the synthesis of pharmaceuticals and natural products because of the operational simplicity and the conveniently available reactants. On the basis of the experimental and theoretical results, a plausible mechanism of aliphatic nucleophilic substitution (S-N) in the cyclization has been postulated and evidence for the formation of a six-membered ring has also been confirmed by means of density functional theory (DFT) calculations.

  DOI：

  10.1021/jo3012896

文献信息

• An Improved Synthesis of 1,4,7-Triazacyclononanes (tacns) and 1,4,7,10-Tetraazacyclododecanes (cyclens)
  作者：Tak Chan、Jianying Huang、Zhongyuan Zhou

  DOI：10.1055/s-0030-1258316

  日期：2010.11

  In the reaction of compound 7 with ethylenediamine (13) according to Scheme 4, it was reported that 1-tosyl-1,4,7-triazacyclononane (9) was obtained in 78% isolated yield. However, after being alerted by other laboratories, we repeated the same reaction under identical experimental conditions and did not obtain compound 9 as the product of the reaction. While the compound obtained was isomeric with

  据报道，在方案7的化合物7与乙二胺（13）的反应中，以78％的分离产率获得了1-甲苯磺酰基-1,4,7-三氮杂环壬烷（9）。但是，在其他实验室发出警告后，我们在相同的实验条件下重复了相同的反应，但未获得化合物9作为反应产物。而获得的化合物为异构体与9根据其质谱，其1 H NMR谱是相似但不完全相同的9，根据方案2，其可能是由备用路由能够得到和独立地合成的公知的化合物¹更重要的是，所得产物的13 C NMR谱具有四个芳族和五个脂族碳信号，并且与具有八个碳信号的1-甲苯基-1,4,7-三氮杂环壬烷（9）的谱明显不同。产物被指定具有结构1-（2'-氨基乙基）-4-甲苯磺酰基哌嗪（23）（方案4的修订版）。六元环的形成与7与N，N-二甲基乙二胺（10）反应生成1-甲基-4-甲苯磺酰基哌嗪（11）的反应一致，如方案3中所述。 修订方案4：7与13的反应 我们还使用回流的乙腈中的碳酸钾重新检查了7与1
• One-Step Cyclization: Synthesis of <i>N</i>-Heteroalkyl-<i>N</i>′-tosylpiperazines
  作者：Jianying Huang、Weiyuan Xu、Hujun Xie、Shijun Li

  DOI：10.1021/jo3012896

  日期：2012.9.7

  Piperazine derivatives are important intermediates in organic synthesis and useful building blocks in pharmaceutical and fine chemical industries. Currently available synthetic routes for these heterocyclic compounds have limited scope owing to the harsh reaction conditions, low yields, and multistep process. Herein, we reported a practical method for synthesis of alkyl-, alcohol-, amine-, and ester-extended tosylpiperazines under mild conditions with moderate to high yields. This protocol exhibits potential applicability in the synthesis of pharmaceuticals and natural products because of the operational simplicity and the conveniently available reactants. On the basis of the experimental and theoretical results, a plausible mechanism of aliphatic nucleophilic substitution (S-N) in the cyclization has been postulated and evidence for the formation of a six-membered ring has also been confirmed by means of density functional theory (DFT) calculations.