6-amino-4-(3,4-dioxymethylenephenyl)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-amino-4-(3,4-dioxymethylenephenyl)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole
• 英文别名: 6-Amino-4-(1,3-benzodioxol-5-yl)-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile；6-amino-4-(1,3-benzodioxol-5-yl)-3-methyl-1-phenyl-4H-pyrano[2,3-c]pyrazole-5-carbonitrile
• 化学式: C₂₁H₁₆N₄O₃
• 分子量: 372.383
• InChiKey: BAGACSWTXUDNOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  95.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  胡椒醛 、 依达拉奉 、 丙二腈 在 十六烷基三甲基溴化铵 作用下， 以 水 为溶剂， 反应 3.0h， 以79%的产率得到6-amino-4-(3,4-dioxymethylenephenyl)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole
  参考文献：
  名称：

  6-氨基-4-芳基-5-氰基-3-甲基-1-苯基-1,4-二氢吡喃[2,3-c]吡唑在水中的清洁简单合成

  摘要：

  摘要 一种以芳香醛、丙二腈和 3-甲基为原料制备 6-氨基-4-芳基-5-氰基-3-甲基-1-苯基-1,4-二氢吡喃并[2,3-c]吡唑的简单清洁方法描述了在水中由十六烷基三甲基溴化铵 (HTMAB) 催化的 -1-苯基-2-吡唑啉-5-one。该方法具有多种优点，例如反应条件温和、后处理程序简单且对环境友好。

  DOI：

  10.1081/scc-200046527

文献信息

• Greener approach towards the facile synthesis of 1,4-dihydropyrano[2,3-c]pyrazol-5-yl cyanide derivatives at room temperature
  作者：Ravi S. Balaskar、Sandip N. Gavade、Madhav S. Mane、Bapurao B. Shingate、Murlidhar S. Shingare、Dhananjay V. Mane

  DOI：10.1016/j.cclet.2010.06.013

  日期：2010.10

  This report describes triethylammonium acetate (TEAA) ionic liquid catalyzed one pot synthesis of 6-amino-4-aryl-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazoles by the reaction of aromatic aldehyde, malononitrile and 3-methyl-1-phenyl-2-pyrazolin-5-one at room temperature. TEAA plays dual role as reaction media and catalyst. It can also be easily recovered and reused in several runs. TEAA

  这份报告描述了乙酸三乙铵（TEAA）离子液体催化的一锅合成6-氨基-4-芳基-5-氰基-3-甲基-1-苯基-1,4-二氢吡喃并[2,3-c]吡唑芳香醛，丙二腈和3-甲基-1-苯基-2-吡唑啉-5-酮在室温下的反应 TEAA作为反应介质和催化剂起着双重作用。它也可以轻松地恢复并在多个运行中重复使用。TEAA提供了更绿色的反应方案来提供无需使用有机溶剂，昂贵且有毒的催化剂的方法。
• A Clean and Simple Synthesis of 6‐Amino‐4‐Aryl‐5‐Cyano‐3‐Methyl‐1‐Phenyl‐1,4‐Dihydropyrano[2,3‐<i>c</i>]Pyrazole in Water
  作者：Tong‐Shou Jin、Ai‐Qing Wang、Zhao‐Li Cheng、Jian‐She Zhang、Tong‐Shuang Li

  DOI：10.1081/scc-200046527

  日期：2005.1.1

  A simple and clean method for producing 6‐amino‐4‐aryl‐5‐cyano‐3‐methyl‐1‐phenyl‐1,4‐ dihydropyrano[2,3‐c]pyrazole from aromatic aldehyde, malononitrile and 3‐methyl‐1‐phenyl‐ 2‐pyrazolin‐5‐one catalyzed by hexadecyltrimethylammonium bromide (HTMAB) in water is described. This method provides several advantages such as mild reaction conditions, simple workup procedure, and being environmentally friendly

  摘要 一种以芳香醛、丙二腈和 3-甲基为原料制备 6-氨基-4-芳基-5-氰基-3-甲基-1-苯基-1,4-二氢吡喃并[2,3-c]吡唑的简单清洁方法描述了在水中由十六烷基三甲基溴化铵 (HTMAB) 催化的 -1-苯基-2-吡唑啉-5-one。该方法具有多种优点，例如反应条件温和、后处理程序简单且对环境友好。
• Sulfamic Acid Catalysed One-Pot Three-Component Condensation for the Synthesis of 1,4-dihydropyrano[2,3-<i>c</i>]pyrazoles
  作者：Sandeep V. Shinde、Wamanrao N. Jadhav、Jeevan M. Kondre、Sumit V. Gampawar、Nandkishor N. Karade

  DOI：10.3184/030823408x321051

  日期：2008.5

  A clean and simple synthesis of 6-amino-4-aryl-3-methyl-1-phenyl-1,4-dihydropyrano[2,3- c]pyrazole-5-carbonitriles was accomplished in good to excellent yields via the one-pot three component condensation of 3-methyl-1-phenyl-2-pyrazolin-5-one, an aromatic aldehyde, and malononitrile catalysed by sulfamic acid in ethanol.

  在氨基磺酸催化下，在乙醇中通过 3-甲基-1-苯基-2-吡唑啉-5-酮、芳香醛和丙二腈的单锅三组分缩合反应，以良好到极佳的收率完成了 6-氨基-4-芳基-3-甲基-1-苯基-1,4-二氢吡喃并[2,3-c]吡唑-5-甲腈的简便合成。
• Solvent‐Free, One‐Pot Synthesis of Pyrano[2,3‐c]pyrazole Derivatives in the Presence of KF·2H₂O by Grinding
  作者：Zhongjiao Ren、Weiguo Cao、Weiqi Tong、Zhu Jin

  DOI：10.1080/00397910500212809

  日期：2005.10

  A solvent-free, one-pot process for the preparation of 4H-pyrans in the presence of KF center dot 2H(2)O by grinding was achieved. Its advantages are easy workup, mild reaction conditions, high yields, and environmental friendliness.
• Three‐Component One‐Pot Synthesis of 1,4‐Dihydropyrano[2,3‐<i>c</i>]pyrazole Derivatives in Aqueous Media
  作者：Daqing Shi、Jie Mou、Qiya Zhuang、Lihui Niu、Nan Wu、Xiangshan Wang

  DOI：10.1081/scc-200043224

  日期：2004.1

  6-Amino-5-cyano-4-aryl-1,4-dihydropyrano[2,3-c]pyrazoles were synthesized by three-component reaction of aromatic aldehydes, malononitrile, and 3-methyl-1-phenyl-2-pyrazolin-5-one using triethylbenzylammonium chloride (TEBA) as catalyst in aqueous media. The reaction has the advantages of good yield, less pollution, ease of separation, and of being environment friendly.