ethyl 2-amino-5',7,7-trimethyl-2',5-dioxo-1',2',5,6,7,8-hexahydrospiro[chromene-4,3'-indole]-3-carboxylate | 1174672-84-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl 2-amino-5',7,7-trimethyl-2',5-dioxo-1',2',5,6,7,8-hexahydrospiro[chromene-4,3'-indole]-3-carboxylate
• 英文别名: ethyl 2-amino-5',7,7-trimethyl-2',5-dioxo-5,6,7,8-tetrahydrospiro[chromene-4,3'-indoline]-3-carboxylate；ethyl 2'-amino-5,7',7'-trimethyl-2,5'-dioxospiro[1H-indole-3,4'-6,8-dihydrochromene]-3'-carboxylate
• CAS: 1174672-84-4
• 化学式: C₂₂H₂₄N₂O₅
• 分子量: 396.443
• InChiKey: KLEGJJPYJVYBAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl cyano(5-methyl-2-oxo-2,3-dihydro-1H-indol-3-ylidene)acetate 、 5,5-二甲基-1,3-环己二酮 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 ethyl 2-amino-5',7,7-trimethyl-2',5-dioxo-1',2',5,6,7,8-hexahydrospiro[chromene-4,3'-indole]-3-carboxylate
  参考文献：
  名称：

  合成新的杂环系统-取代的螺[chromene-4,3'-吲哚]和螺[吲哚-3,4'-喹啉]

  摘要：

  已经开发了通过靛红与5,5-二甲基环己烷的碱催化多米诺反应合成新的杂环系统，螺环[chromene-4,3'-吲哚]和螺环[吲哚-3,4'-喹啉]的方法。 -1，3-二酮（或5，5-二甲基-3-苯胺基环己二-2-烯-1-酮）和氰基乙酸乙酯。

  DOI：

  10.1134/s1070428016090098

文献信息

• NaCl as a Novel and Green Catalyst for the Synthesis of Biodynamic Spiro Heterocycles in Water Under Sonication
  作者：Anshu Dandia、Anuj Kumar Jain、Dharmendra Singh Bhati

  DOI：10.1080/00397911.2010.515365

  日期：2011.10

  Abstract An efficient and novel green catalytic protocol for the synthesis of biologically important spirooxindole derivatives is developed in a one-pot, three-component approach involving substituted isatin, activated methylene reagent, and 3-methyl-1-phenyl-2-pyrazolin-5-one in water under sonication. This report describes the use of sodium chloride as a nonacidic and green catalyst for a variety

  摘要 一种用于合成具有生物学意义的螺羟吲哚衍生物的高效、新颖的绿色催化方案是通过一锅、三组分的方法开发的，包括取代的靛红、活化的亚甲基试剂和 3-methyl-1-phenyl-2-pyrazolin-5 - 一个在水中超声处理。本报告描述了氯化钠作为各种底物的非酸性和绿色催化剂的用途。这种方法的优点是环境友好、操作简单、产量高、易于处理以及产品不需要纯化。
• Step-economic, efficient, ZnS nanoparticle-catalyzed synthesis of spirooxindole derivatives in aqueous medium via Knoevenagel condensation followed by Michael addition
  作者：Anshu Dandia、Vijay Parewa、Anuj Kumar Jain、Kuldeep S. Rathore

  DOI：10.1039/c1gc15244k

  日期：——

  An environmentally friendly, one-pot, three-component ZnS nanoparticle-mediated synthesis of biologically important spirooxindole derivatives in water under ultrasonic irradiation is described herein. ZnS nanoparticles were synthesized by aqueous chemical method. The advantages of this method lies in its simplicity, cost effectiveness, environment friendliness, easier scaling up for large scale synthesis without using high pressure, temperature and toxic chemicals. Greenness of the process was well instituted as water was exploited both as reaction media as well as medium for synthesis of catalyst (ZnS nanoparticles). The particle size was determined by transmission electron microscopy (TEM) and XRD. Compared with other methods for synthesis of spirooxindole derivatives, satisfactory results were obtained with high yields, short reaction time, with simple experimental procedure. After reaction course, the ZnS NPs can be recycled and reused without any apparent loss of activity.

  本文介绍了一种在超声波辐照下，以 ZnS 纳米粒子为介导，在水中合成具有重要生物活性的螺吲哚衍生物的环保型一锅三组份合成方法。ZnS 纳米粒子采用水化学方法合成。这种方法的优点在于简单、成本效益高、环境友好，而且无需使用高压、高温和有毒化学品，更容易进行大规模合成。由于水既可用作反应介质，也可用作合成催化剂（ZnS 纳米粒子）的介质，因此该工艺绿色环保。粒度由透射电子显微镜（TEM）和 XRD 确定。与其他合成螺吲哚衍生物的方法相比，该方法产率高、反应时间短、实验过程简单，取得了令人满意的结果。反应过程结束后，ZnS NPs 可回收再利用，且没有明显的活性损失。
• Magnetic calcined oyster shell functionalized with taurine immobilized on β-cyclodextrin (Fe3O4/COS@β-CD-SO3H NPs) as green and magnetically reusable nanocatalyst for efficient and rapid synthesis of spirooxindoles
  作者：Narges Mohammadian、Batool Akhlaghinia

  DOI：10.1007/s11164-019-03860-x

  日期：2019.10

  16–25 nm. The new magnetic nanocatalyst (Fe3O4/COS@β-CD-SO3H NPs) was found to be very effective in one-pot multi-component reaction of isatin, active methylene component, and 1,3-dicarbonyl compounds for rapid preparation of spirooxindoles with fused chromenes in water in excellent yield. The most promising features of the presented approach are the short reaction time (15–22 min), magnetic separation of

  摘要 固定在β环糊精牛磺酸官能磁性煅牡蛎壳（FE 3 ö 4 / COS @β-CD-SO 3H NPs是作为一种新的稳定，长寿命，高效和优异的可重复使用的磁性纳米结构催化剂制备的。所制备的固体酸性催化剂通过各种光谱和显微技术进行表征，例如傅立叶变换红外（FT-IR）光谱，X射线衍射（XRD）分析，扫描电子显微镜（SEM），能量色散X射线（EDX）光谱，透射电子显微镜（TEM），振动样品磁力法（VSM），热重分析（TGA）/差热重分析（DTG）和元素（CHNS）分析。结果清楚地表明，合成的超顺磁性催化剂以均匀的球形存在，平均粒径为16-25 nm。新的磁性纳米催化剂（FE 3 ö 4 / COS @β-CD-SO 3已发现H NPs在伊斯兰法，活性亚甲基组分和1,3-二羰基化合物的一锅多组分反应中非常有效，可在水中以优异的产率快速制备带有稠合色烯的螺硫醇。提出的方法最有希望的特点是反应时间
• An Efficient Method for Multicomponent Synthesis of Spiro[4H-pyran-oxindole] Derivatives Catalyzed by Magnesium Perchlorate
  作者：Chunlei Wu、Runpu Shen、Jianhui Chen、Chunqi Hu

  DOI：10.5012/bkcs.2013.34.8.2431

  日期：2013.8.20

  A simple and efficient method for the synthesis of spiro[4H-pyran-oxindole] derivatives by means of three-component reactions between isatins, malononitrile or ethyl cyano-acetate, and 1,3-dicarbonyl compounds in the presence of catalytic amount of magnesium perchlorate in 50% aqueous ethanol medium has been described.

  一种简单高效的方法已被描述，用于通过三组分反应合成螺[4H-吡喃-喹啉]衍生物，该反应涉及吲哚酮、马来腈或乙基氰乙酸盐，以及含有1,3-二酮化合物，并在50%乙醇水溶液中催化剂为少量高氯酸镁的条件下进行。
• Synthesis of fused 2′-amino-3′-R-spiro-[indole-3,4′-pyran]-2(1H)-ones
  作者：L. A. Shemchuk、V. P. Chernykh、R. G. Red’kin

  DOI：10.1134/s1070428008120117

  日期：2008.12

  An efficient one-pot procedure has been proposed for the synthesis of fused 2'-amino-3'-R-spiro-[indole-3,4'-pyran]-2(1H)-ones via base-catalyzed three-component condensation of isatins with the corresponding nitriles and 1,3-diketones.