3-(6-chloro-9H-purin-9-yl)propanenitrile | 4244-40-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 3-(6-chloro-9H-purin-9-yl)propanenitrile
• 英文别名: 3-(6-chloropurin-9-yl)propionitrile；6-chloro-9H-purin-9-ylpropionitrile；6-chloro-9H-purine-9-propanenitrile；6-chloro-9-(2-cyanoethyl)purine；3-(6-chloro-purin-9-yl)-propionitrile；6-Chlor-9H-purin-9-ylpropionitril；3-(6-chloropurin-9-yl)propanenitrile
• CAS: 4244-40-0
• 化学式: C₈H₆ClN₅
• mdl: MFCD01325809
• 分子量: 207.622
• InChiKey: HLBNMSUAAPNUJF-UHFFFAOYSA-N

物化性质

• 熔点：
  149.5-151.5 °C
• 沸点：
  443.7±55.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-(6-chloro-9H-purin-9-yl)propanenitrile 在 碘 、 碳酸氢钠 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 85.0h， 生成 N-[7-(3-methylbut-2-enyl)purin-6-yl]hydroxylamine
  参考文献：
  名称：

  Synthesis of 9-Substituted Tetrahydrodiazepinopurines:  Studies toward the Total Synthesis of Asmarines

  摘要：

  A methodology for the preparation of asmarine analogues has been developed. The asmarines are cytotoxic marine alkaloids with a unique tetrahydro[1,4]diazepino[1,2,3-g,h]purine (THDAP) structure. Three cyclization methods were applied for the preparation of the 9,9-disubstituted 10-hydroxy-THDAP system, namely, aminomercurization, iodocyclization, and acid-catalyzed cyclization. The DMPM group of the NOH functionality and cyanoethyl group of the N-9 atom were found to be the most suitable protecting groups. The structures of all compounds were mainly determined from NMR measurements including N-15 chemical shifts obtained from (NH)-N-15 HMBC spectra. The end products are at least about 1 order of magnitude less active than the natural product asmarine B.

  DOI：

  10.1021/jo048622g
• 作为产物：
  描述：

  丙烯腈 、 6-氯嘌呤 在 三乙胺 作用下， 以 水 为溶剂， 反应 0.08h， 以82%的产率得到3-(6-chloro-9H-purin-9-yl)propanenitrile
  参考文献：
  名称：

  Microwave-Promoted Michael Addition in Neat Water: A Rapid, Efficient and Green Method for the Preparation of Acyclic Nucleosides

  摘要：

  在微波辐射的帮助下，实现了在水中合成无环核苷的过程，提供了一种快速、高效和便利的无环核苷高产量制备方法。

  DOI：

  10.1055/s-2007-970772

文献信息

• Efficient synthesis of nebularine and vidarabine via dehydrazination of (hetero)aromatics catalyzed by CuSO₄in water
  作者：Ran Xia、Ming-Sheng Xie、Hong-Ying Niu、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.1039/c3gc41658e

  日期：——

  A simple dehydrazination reaction has been achieved in the presence of a catalytic amount of CuSO4 for the first time. With CuSO4 (2 mol%) as a catalyst and water as a solvent, the dehydrazination products were obtained in good yields (66–95%). Moreover, the drugs nebularine and vidarabine were afforded successfully, and vidarabine could be produced on a 0.923 kg scale, which shows good potential for industrial applications.

  首次在催化量的CuSO4存在下实现了一步简单的脱氢反应。以CuSO4 (2 mol%)为催化剂，水为溶剂，脱氢产物获得了良好的产率（66-95%）。此外，成功合成了药物 nebularine 和 Vidarabine，并且 Vidarabine 可在0.923公斤规模生产，显示出良好的工业应用潜力。
• Preparation of derivatives of 1-(2-pyrimidinyl)piperazine as potential antianxiety, antidepressant, and antipsychotic agents
  作者：Irwin Becker

  DOI：10.1002/jhet.5570450410

  日期：2008.7

  This paper describes the preparation of twenty-eight derivatives of 1-(2-pyrimidinyl)piperazine as potential antianxiety, antidepressant, and antipsychotic agents. In twenty-six of the preparations a chloro nitrogen heterocycle was caused to react with an excess of 1-(2-pyrimidinyl)piperazine in the absence of solvent. A specific example is given above.

  本文介绍了1-（2-嘧啶基）哌嗪28种衍生物的制备，它们可作为潜在的抗焦虑药，抗抑郁药和抗精神病药。在不存在溶剂的情况下，在26种制剂中，使氯氮杂环与过量的1-（2-嘧啶基）哌嗪反应。上面给出了一个具体的例子。
• Antimicrobial and cytotoxic activity of agelasine and agelasimine analogs
  作者：Anders Vik、Erik Hedner、Colin Charnock、Linda W. Tangen、Ørjan Samuelsen、Rolf Larsson、Lars Bohlin、Lise-Lotte Gundersen

  DOI：10.1016/j.bmc.2007.03.086

  日期：2007.6

  Agelasine and agelasimine derivatives with substantially less complicated terpenoid side chains compared to the naturally occurring compounds have been synthesized and their ability to inhibit growth of microorganisms and cancer cells has been studied. Compounds with excellent activity against cancer cell lines (MIC ca. 1 microM for the most potent compounds), including a drug resistant renal cell

  与天然化合物相比，已经合成了具有实质上不那么复杂的萜类化合物侧链的Agelasine和agelasimine衍生物，并研究了它们抑制微生物和癌细胞生长的能力。已经鉴定出对癌细胞系具有优异活性的化合物（对于最有效的化合物，MIC约为1 microM），包括抗药性肾细胞系。研究的大多数化合物还表现出广谱的抗菌活性，包括抗结核分枝杆菌的活性。
• Metal‐Free, Light‐Mediated, Site‐Specific, Radical C6−H Alkylation of Purines with Alcohols Intervened by Oxalates without Catalysts
  作者：Gang Liu、Xianfeng Mu、Miao Tian、Weili Wang、Chunhui Zou、Yiwen Chen、Mingwu Yu

  DOI：10.1002/ejoc.202201491

  日期：——

  A mild and practical protocol for highly regioselective C6−H alkylation of purines with alcohols intervened by oxalates under blue LED irradiation is reported. This transformation does not need transition metal catalysts, is not sensitive to moisture and does not require N2 protection. Besides, this method displays broad functional groups compatibility and is easily scale up.

  报告了一种温和实用的方案，用于在蓝色 LED 照射下草酸盐干预嘌呤与醇的高度区域选择性 C6-H 烷基化。这种转化不需要过渡金属催化剂，对水分不敏感，也不需要N 2保护。此外，该方法显示出广泛的功能组兼容性并且易于放大。
• Metal-free, direct acylation of purines to access C⁶-acylated purine derivatives induced by TBHP <i>via</i> Minisci-type reaction
  作者：Chunhui Zou、Mingwu Yu、Zhongkai Jiang、Xiguang Liu、Yiwen Chen、Lele Zhang

  DOI：10.1039/d3nj05712g

  日期：——

  A metal-free C–H functionalization of purines with aldehydes was developed to access C6-acylated purines via green radical reactions. Theoretically, there are many competitive reactions due to the three C–H bonds (C2–H, C6–H, C8–H) in the purine, and the acylation only happens at the purinyl C6-position. This method avoids a metal catalyst and provides a green approach to construct C–C (sp2) bonds

  开发了一种用醛对嘌呤进行无金属 C-H 官能化的方法，以通过绿色自由基反应获得 C 6 -酰化嘌呤。理论上，由于嘌呤中的三个C-H键（C 2 -H、C 6 -H、C 8 -H），存在多种竞争反应，酰化仅发生在嘌呤基C 6位。该方法避免了金属催化剂，提供了一种在嘌呤基C 6位构建C-C (sp 2 )键的绿色方法，同时保持与各种官能团的优异相容性。此外，该协议具有广泛的底物范围和易于放大的特点。产品的转化证明了该方法具有显着的实用价值。主要机制是根据对照实验提出的。