(R)-6′-amino-1-benzyl-3′-methyl-2-oxo-1′-phenyl-1′H-spiro[indoline-3,4′-pyrano[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: (R)-6′-amino-1-benzyl-3′-methyl-2-oxo-1′-phenyl-1′H-spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-5′-carbonitrile
• 英文别名: 6'-Amino-1-benzyl-3'-methyl-2-oxo-1'-phenylspiro[indole-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile
• 化学式: C₂₈H₂₁N₅O₂
• 分子量: 459.507
• InChiKey: HKFWEPCQVAIAAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  97.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-苄基-1H-吲哚-2,3-二酮 、 3-methyl-1-phenyl-1,5-dihydro-4H-pyrazol-4-one 、 丙二腈 在 cesium fluoride 作用下， 以 乙醇 为溶剂， 反应 0.12h， 以99%的产率得到(R)-6′-amino-1-benzyl-3′-methyl-2-oxo-1′-phenyl-1′H-spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-5′-carbonitrile
  参考文献：
  名称：

  CsF促进了室温下乙醇中螺氧杂吲哚-吡喃环杂环的快速合成

  摘要：

  描述了一种新型的，多功能的，直接的合成策略，用于构建功能化螺氧杂吲哚-吡喃环杂环。该程序基于室温下在乙醇中，由CsF促进的快速串联串联的Isatin，丙二腈和4-羟基香豆素/巴比妥酸/吡唑啉酮的Knoevenagel-Michael-环缩合反应。该方法具有多种优势，例如操作简便，在短反应时间内（3-25分钟）即可获得出色的收率，以及产物的简单分离。CsF兼具碱和羰基活化剂的作用。

  DOI：

  10.1002/jhet.3846

文献信息

• N,2-Dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide: an efficient and homogeneous catalyst for one-pot synthesis of 4H-pyran, pyranopyrazole and pyrazolo[1,2-b]phthalazine derivatives under aqueous media
  作者：Ardeshir Khazaei、Mohammad Ali Zolfigol、Fatemeh Karimitabar、Iraj Nikokar、Ahmad Reza Moosavi-Zare

  DOI：10.1039/c5ra10730j

  日期：——

  1-dioxide (DCDBTSD) as a highly efficient and homogeneous catalyst was successfully applied for the synthesis of 4H-pyran, pyranopyrazole and pyrazolo[1,2-b]phthalazine derivatives by a one-pot multi-component reaction (MCR) in water. The described method has some advantages such as mild and neutral reaction media, high yields, short reaction times, cleaner and easier reaction profiles and compliance with

  N，2-二溴-6-氯-3,4-二氢-2 H-苯并[ e ] [1,2,4]噻二嗪-7-磺酰胺1,1-二氧化物（DCDBTSD）作为高效且均相的催化剂通过一锅多组分反应（MCR）在水中成功地将其用于合成4 H-吡喃，吡喃并吡唑和吡唑并[1,2- b ]酞嗪衍生物。所描述的方法具有一些优点，例如温和和中性的反应介质，高收率，较短的反应时间，更清洁和更容易的反应过程以及符合绿色化学方案。
• Ultrasound Promoted Green Synthesis of Spiro Indoline-3,4′-pyrano[2,3-<i>c</i>]pyrazoles
  作者：S. F. Hojati、S. Mohamadi

  DOI：10.1080/00304948.2020.1762458

  日期：2020.7.3

  Pyranopyrazoles make up one of the interesting classes of oxygen-containing heterocycles 1 known to have valuable medicinal properties such as anti-dysplasia, hypoglycaemic, 2 anti-microbial, 3 ant...

  吡喃并吡唑是一类有趣的含氧杂环化合物 1，已知具有有价值的药用特性，例如抗发育不良、降血糖、2 抗微生物、3 抗...
• Novel organometallic nanomagnetic catalyst for multicomponent synthesis of spiroindoline derivatives
  作者：Seyedeh Fatemeh Hojati、Amirhassan Amiri、Sakineh Mohamadi、Nasrin MoeiniEghbali

  DOI：10.1007/s11164-017-3228-5

  日期：2018.4

  characterized by Fourier-transform infrared (FT-IR) spectroscopy, transmission electron microscopy (TEM), and X-ray diffraction (XRD) analysis, and applied for four-component synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] derivatives from isatin, hydrazine hydrate or phenylhydrazine, ethyl acetoacetate, and malononitrile or ethyl cyanoacetate in aqueous medium at room temperature. Use of water as safe

  制备了一种新型的可重复使用的绿色聚苯胺（PANI）/ Fe 3 O 4 /碳纳米管（CNT）纳米磁性催化剂，其特征在于具有傅里叶变换红外光谱（FT-IR），透射电子显微镜（TEM）和X-射线衍射（XRD）分析，并用于由靛红，水合肼或苯肼，乙酰乙酸乙酯和丙二腈或乙基四氢吡咯并[吲哚啉-3,4'-吡喃并[2,3- c ]吡唑]衍生物的四组分合成在室温下于水性介质中使用氰基乙酸盐。使用水作为安全且对环境无害的溶剂，反应时间短，产物收率高，后处理步骤容易，催化剂易于分离和可重复使用是该方法的显着优势。
• Enantioselective synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] derivatives via an organocatalytic asymmetric Michael/cyclization cascade reaction
  作者：Jin Xie、Xiao-Yu Xing、Feng Sha、Zhi-Yan Wu、Xin-Yan Wu

  DOI：10.1039/c6ob01256f

  日期：——

  An efficient enantioselective synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] derivatives by a cascade reaction between pyrazolones and isatylidene malononitriles is described. With only 1 mol% of (DHQD)2PYR, chiral spirooxindole derivatives have been produced in excellent yields (96–99%) with good-to-excellent enantioselectivities (up to 91% ee).

  描述了通过吡唑啉酮和异亚丙基丙二腈之间的级联反应有效地合成螺[吲哚啉-3,4'-吡喃并[2,3- c ]吡唑]衍生物的对映体。仅用1 mol％的（DHQD）2 PYR，就可以以优异的收率（96–99％）和良好至优异的对映选择性（高达91％ee）制备手性螺氧基吲哚衍生物。
• Ultrasound promoted green synthesis of spiro[pyrano[2,3-c]pyrazoles] as antioxidant agents
  作者：Anshu Dandia、Deepti Saini、Sumit Bhaskaran、Dinesh Kumar Saini

  DOI：10.1007/s00044-013-0671-8

  日期：2014.2

  Ultrasound promoted, cerium ammonium nitrate catalyzed sustainable synthesis of spiro[indoline3,4'-pyrano[2,3-c]pyrazole] derivatives (4a-l) is reported herein. The synthesized compounds were screened for their antioxidant activities as free radical scavenging effect on diphenylpicryl hydrazine (DPPH center dot), 2,2'-azino-bis(3-ethylbenzthiazoline- 6-sulphonic acid) (ABTS(center dot+)) and nitric oxide (NO) radicals. The screened compounds showed potent scavenging activities against DPPH center dot, ABTS(center dot+) and NO radicals. In order to further extend on studies and to obtain a deep insight into structure activity relationship of this class of compounds, we designed N-substitution of indole moiety with the aim to study its antioxidant potential.