(S)-6-amino-3-methyl-1,4-diphenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S)-6-amino-3-methyl-1,4-diphenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
• 英文别名: (R)-6-amino-1,4-dihydro-3-methyl-1,4-diphenylpyrano[2,3-c]-pyrazole-5-carbonitrile；6-amino-3-methyl-1,4-diphenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile；(4S)-6-amino-3-methyl-1,4-diphenyl-4H-pyrano[2,3-c]pyrazole-5-carbonitrile
• 化学式: C₂₀H₁₆N₄O
• 分子量: 328.373
• InChiKey: PRYBIJAJECYWEP-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  76.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-benzylidene-3-methyl-1-phenylpyrazolone 、 丙二腈 在 3-[[[3,5-双（三氟甲基）苯基]氨基]-4-[[（（1R，2R）-2-（二甲基氨基）-1,2-二苯基乙基]氨基]-3-环丁烯-1,2-二酮 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 以81%的产率得到(S)-6-amino-3-methyl-1,4-diphenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
  参考文献：
  名称：

  4-亚苄基-3-甲基吡唑-5-酮和丙二腈的有机催化不对称串联迈克尔环化反应：吡喃并[2,3- c ]吡唑支架的立体控制结构†

  摘要：

  开发了一种有效的立体控制吡喃并[2,3- c ]吡唑支架的方法。在衍生自（1 R，2 R）-1,2-二苯乙烷-1,2-二胺的双官能方酰胺的催化下，4-苄叉基吡唑-5（4 H）-的不对称串联迈克尔加成/环化反应与丙二腈有效地进行，以令人满意的产率提供了所需的吡喃并[2,3- c ]吡唑类，并具有高水平的对映体选择性（至多99％ee）。

  DOI：

  10.1039/c5ra04356e

文献信息

• Enantioselective Synthesis of<i>N</i>-Phenyl-dihydropyrano[2,3-<i>c</i>]pyrazoles via Cascade Michael Addition/Thorpe-Ziegler Type Cyclization Catalyzed by a Chiral Squaramide
  作者：Junhua Li、Daming Du

  DOI：10.1002/cjoc.201400829

  日期：2015.4

  Enantioselective synthesis of biologically active dihydropyrano[2,3‐c]pyrazoles has been achieved through a squaramide‐catalysed Michael addition/Thorpe‐Ziegler type cyclization cascade reaction between arylidenepyrazolones and malononitrile. A series of optically active dihydropyano[2,3‐c]pyrazoles were obtained in excellent yields (up to 99%) and moderate to good enantioselectivities (up to 79% ee)

  具有生物活性的二氢吡喃并[2,3- c ]吡唑的对映选择性合成是通过对苯二酚吡唑并酮和丙二腈之间的方胺催化的Michael加成反应/ Thorpe-Ziegler型环化级联反应实现的。在温和的反应条件下，以优异的收率（高达99％）和中等至良好的对映选择性（高达79％ee）获得了一系列光学活性的二氢吡喃并[2,3- c ]吡唑。
• Enantioselective synthesis of functionalized fluorinated dihydropyrano [2,3-c]pyrazoles catalyzed by a simple bifunctional diaminocyclohexane-thiourea
  作者：Hong-Fei Zhang、Zheng-Qing Ye、Gang Zhao

  DOI：10.1016/j.cclet.2014.01.034

  日期：2014.4

  Abstract Enantioselective synthesis of functionalized fluorinated dihydropyrano[2,3-c]pyrazoles has been achieved via a diaminocyclohexane-thiourea catalyzed cascade Michael addition and Thorpe-Ziegler type cyclization in high yields (up to 98%) with moderate to good enantioselectivity (up to 90% ee ).

  摘要通过二氨基环己烷-硫脲催化的级联迈克尔加成反应和Thorpe-Ziegler型环化反应，以高产率（高达98％）和中等至良好的对映选择性（可达90％ee）。
• Mechanistic Insights into Annulation of Arylidene‐Δ ² ‐Pyrrolin‐4‐Ones by Cinchona Squaramide‐Based Organocatalysts
  作者：Luka Ciber、Sebastijan Ričko、Jure Gregorc、Franc Požgan、Jurij Svete、Helena Brodnik、Bogdan Štefane、Uroš Grošelj

  DOI：10.1002/adsc.202101369

  日期：2022.3

  AbstractArylidene‐Δ2‐pyrrolin‐4‐ones undergo organocatalyzed annulation with malononitrile, furnishing dihydropyrano[3,2‐b]pyrroles (18 examples, 0–77% ee in dichloromethane, 11–44% ee in methanol). The products could be enantiomerically enriched by trituration (11 examples, 95–99% ee). Enantioselectivity was dependent on the nature of the substrate and the conformation of the catalyst, which in turn was solvent‐controlled. The reaction mechanism, which included two pseudo‐enantiomeric organocatalyst conformations, was investigated by experimental and quantum chemical methods. The reaction mechanism consists of Michael addition reaction step followed by 6‐exo‐dig annulation, which was found to be the rate determining step. Additionally, it was identified that the preferred reaction pathway follows the model originally proposed by Pápai et al.magnified image