(S)-6-amino-3-methyl-1,4-diphenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile | 1599480-93-9

• 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: (S)-6-amino-1,4-dihydro-3-methyl-1,4-diphenylpyrano[2,3-c]-pyrazole-5-carbonitrile；(R)-6-amino-3-methyl-1,4-diphenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile；(4R)-6-amino-3-methyl-1,4-diphenyl-4H-pyrano[2,3-c]pyrazole-5-carbonitrile
• CAS: 1599480-93-9
• 化学式: C₂₀H₁₆N₄O
• 分子量: 328.373
• InChiKey: PRYBIJAJECYWEP-SFHVURJKSA-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 1-[3,5-双(三氟甲基)苯基]-3-[(1R,2R)-(-)-2-(二甲氨基)环己基]硫脲 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以95%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：

  手性的1,4-二氢吡喃(2,3-c)吡唑衍生物及其合 成方法和应用

  摘要：

  本发明公开了一种手性的1,4‑二氢吡喃(2,3‑c)吡唑衍生物及其合成方法和应用，其合成方法包括：以甲苯为溶剂，在Takemoto催化剂催化下，将取代或未取代的吡唑啉酮衍生物和丙二腈进行反应，反应产物经后处理得到手性的1,4‑二氢吡喃(2,3‑c)吡唑衍生物。该方法具有反应时间灵活，收率较高，操作简便等优点，适用范围广。本发明手性的1,4‑二氢吡喃(2,3‑c)吡唑衍生物对革兰氏阳性菌和革兰氏阴性菌有抑制的作用。

  公开号：

  CN103910737B

文献信息

• 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）。
• Organocatalyzed asymmetric tandem Michael-cyclization reaction of 4-benzylidene-3-methylpyrazol-5-ones and malononitrile: stereocontrolled construction of pyrano[2,3-c]pyrazole scaffold
  作者：H.-X. Wang、L.-L. Wu、Y.-M. Wang、Z.-H. Zhou

  DOI：10.1039/c5ra04356e

  日期：——

  An efficient approach for the stereocontrolled construction of pyrano[2,3-c]pyrazole scaffold has been developed. Under the catalysis of a bifunctional squaramide derived from (1R,2R)-1,2-diphenylethane-1,2-diamine, the asymmetric tandem Michael addition/cyclization reaction of 4-benzylidenepyrazol-5(4H)-ones and malononitrile proceeded efficiently to furnish the desired pyrano[2,3-c]pyrazoles in satisfactory

  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）。
• 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