2-amino-5'-methyl-2',5-dioxo-1',2',5,6,7,8-hexahydrospiro[chromene-4,3'-indole]-3-carbonitrile | 304870-78-8

• 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: 2-amino-5'-methyl-2',5-dioxo-1',2',5,6,7,8-hexahydrospiro[chromene-4,3'-indole]-3-carbonitrile
• 英文别名: 2-amino-5'-methyl-2',5-dioxo-5,6,7,8- tetrahydrospiro[chromene-4,3'-indoline]-3-carbonitrile；2-amino-5'-methyl-2',5-dioxo-5,6,7,8-tetrahydrospiro[chromene-4,3'-indoline]-3-carbonitrile；2'-amino-5-methyl-2,5'-dioxospiro[1H-indole-3,4'-7,8-dihydro-6H-chromene]-3'-carbonitrile
• CAS: 304870-78-8
• 化学式: C₁₈H₁₅N₃O₃
• 分子量: 321.335
• InChiKey: FKRJJYXWUMEAKB-UHFFFAOYSA-N

物化性质

• 熔点：
  287 °C (decomp)
• 沸点：
  687.3±55.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3-环己二酮 、 5-methyl-3-dicyanomethylene-2H-indole-2-one 在 三乙醇胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 2-amino-5'-methyl-2',5-dioxo-1',2',5,6,7,8-hexahydrospiro[chromene-4,3'-indole]-3-carbonitrile
  参考文献：
  名称：

  Synthesis of fused 2′-amino-3′-R-spiro-[indole-3,4′-pyran]-2(1H)-ones

  摘要：

  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.

  DOI：

  10.1134/s1070428008120117

文献信息

• Silica-bonded 5-n-propyl-octahydro-pyrimido[1,2-a]azepinium chloride (SB-DBU)Cl as a highly efficient, heterogeneous and recyclable silica-supported ionic liquid catalyst for the synthesis of benzo[b]pyran, bis(benzo[b]pyran) and spiro-pyran derivatives
  作者：Alireza Hasaninejad、Nooshin Golzar、Maryam Beyrati、Abdolkarim Zare、Mohammad Mahdi Doroodmand

  DOI：10.1016/j.molcata.2013.02.022

  日期：2013.6

  The reaction of 3-chloropropyl silica (SilprCl) with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in dry acetone affords silica-bonded 5-n-propyl-octahydro-pyrimido[1,2-a]azepinium chloride (SB-DBU)Cl as a new silica-supported ionic liquid catalyst. Afterward, (SB-DBU)Cl is used for the efficient synthesis of 4H-benzo[b]pyran derivatives via the one-pot, three-component reaction of carbonyl compounds (cyclohexane-1

  3-氯丙基二氧化硅（SilprCl）与1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）在干燥的丙酮中的反应得到二氧化硅键合的5-正丙基-八氢-嘧啶基[1,2- a]氯化ze嗪（SB-DBU）Cl作为新型的二氧化硅负载型离子液体催化剂。之后，（SB-DBU）Cl通过羰基化合物（环己烷-1,3-二酮，5,5-一锅法）的三锅法有效合成4 H-苯并[ b ]吡喃衍生物。（1，3-二甲基环己烷-1，3-二酮或3-甲基-1-苯基-2-吡唑啉-5-酮）与芳族醛和烷基丙二酸酯。此外，一些新颖的双（苯并[ b使用（SB-DBU）Cl合成[] pyran] s和在结构上含有羟吲哚和/或喹喔啉部分的多种结构多样的螺-吡喃。将催化剂循环使用十五次，收率不变。
• Glycerol as a biodegradable and reusable promoting medium for the catalyst-free one-pot three component synthesis of 4H-pyrans
  作者：Hamid Reza Safaei、Mohsen Shekouhy、Sudabeh Rahmanpur、Athar Shirinfeshan

  DOI：10.1039/c2gc35135h

  日期：——

  Glycerol is applied as a green, biodegradable and reusable promoting medium for one-pot three component synthesis of 4H-pyrans under catalyst-free conditions. A broad range of substrates including aromatic and heteroaromatic aldehydes, isatine derivatives, acenaphthenequinone and ninehydrine are condensed with carbonyl compounds possessing a reactive α-methylene group and alkylmalonates. All reactions are completed in short times, and the products are obtained in good to excellent yields. The reaction medium could be recycled and reused several times without any loss of efficiency.

  甘油作为绿色、生物可降解且可重复利用的促进介质，在无催化剂条件下用于一锅法三组分合成4H-吡喃。广泛的一系列底物，包括芳香和杂环醛、吲哚醌衍生物、苊醌和九氢吲哚，与具有活性α-亚甲基的羰基化合物及烷基丙二酸酯进行缩合反应。所有反应均在短时间内完成，产物收率良好至优异。反应介质可回收并重复使用多次，效率无任何损失。
• One-Pot Three-Component Synthesis of Spirooxindoles Catalyzed by Hexamethylenetetramine in Water
  作者：Guo-Dong Wang、Xiao-Nan Zhang、Zhan-Hui Zhang

  DOI：10.1002/jhet.994

  日期：2013.1

  convenient, and multicomponent strategy for synthesis of spirooxindole derivatives has been developed. This strategy provides a rapid access to construct a diversity‐oriented library of spirooxindoles by using three simple and readily available isatin, malononitrile or cyanoacetic ester, and 1,3‐dicarbonyl compound catalyzed by hexamethylenetetramine in water.

  已经开发出一种简单，方便和多组分合成螺环吲哚衍生物的策略。通过使用三种简单易得的Isatin，丙二腈或氰基乙酸酯以及六亚甲基四胺在水中催化的1,3-二羰基化合物，该策略可快速构建以螺菌毒素为导向的多样性文库。
• Versatile three-component synthesis of 2′-amino-1,2-dihydrospiro[(3H)-indole-3,4′-(4′H)-pyran]-2-ones
  作者：V. Yu. Mortikov、Yu. M. Litvinov、A. A. Shestopalov、L. A. Rodinovskaya、A. M. Shestopalov

  DOI：10.1007/s11172-008-0338-7

  日期：2008.11

  2-dihydrospiro[(3H)-indole-3,4′-(4′H)-pyran]-2-ones has been suggested consisting in the three-component reaction of isatins, cyanoacetic acid derivatives, and α-methylenecarbonyl compounds (β-dicarbonyl compounds, activated phenols, and OH-substituted heterocycles) in ethanol in the presence of triethylamine as a catalyst. The reaction proceeds selectively to form spiro[(3H)-indole-3,4′-(4′H)-pyrans].

  一种合成 2'-amino-1,2-dihydrospiro[(3H)-indole-3,4'-(4'H)-pyran]-2-ones 的通用方法包括在三组分中在三乙胺作为催化剂的存在下，靛红、氰乙酸衍生物和 α-亚甲基羰基化合物（β-二羰基化合物、活化酚和 OH 取代的杂环）在乙醇中的反应。该反应选择性地进行以形成螺[(3H)-吲哚-3,4'-(4'H)-吡喃]。
• Synthetic, mechanistic and kinetic studies on the organo-nanocatalyzed synthesis of oxygen and nitrogen containing spiro compounds under ultrasonic conditions
  作者：Nongthombam Geetmani Singh、Makroni Lily、Shougaijam Premila Devi、Noimur Rahman、Aziz Ahmed、Asit K. Chandra、Rishanlang Nongkhlaw

  DOI：10.1039/c6gc00724d

  日期：——

  Vitamin B1 functionalised nano-ferrites: an organo-nanocatalyst for the synthesis of various spiro derivatives.

  维生素B 1官能化的纳米铁氧体：用于合成各种螺衍生物的有机纳米催化剂。