2-amino spiro[(4H)-benzo(h)chromen-4,3'-(3'H)-indol]-(1'H)-2'-one-3-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 2-amino spiro[(4H)-benzo(h)chromen-4,3'-(3'H)-indol]-(1'H)-2'-one-3-carbonitrile
• 英文别名: 2-amino-2'-oxospiro[benzo[h]chromene-4,3'-indoline]-3-carbonitrile；2-amino-2′-oxospiro[benzo[g]chromene-4,3′-indoline]-3-carbonitrile；2-aminospiro[(4H)-benzo(f)chromene-4,3'-(3'H)-indol]-(1'H)-2'-one-3-carbonitrile；2-amino-2′-oxo-1′,2′-dihydrospiro[benzo[h]chromene-4,3′-indole]-3-carbonitrile；2-Amino-2'-oxo-1',2'-dihydrospiro[benzo[h]chromene-4,3'-indole]-3-carbonitrile；2'-amino-2-oxospiro[1H-indole-3,4'-benzo[h]chromene]-3'-carbonitrile
• 化学式: C₂₁H₁₃N₃O₂
• 分子量: 339.353
• InChiKey: DNQUFLBHBAQQQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino spiro[(4H)-benzo(h)chromen-4,3'-(3'H)-indol]-(1'H)-2'-one-3-carbonitrile 在 N-氯代丁二酰亚胺 作用下， 以 甲醇 为溶剂， 以70%的产率得到3-chloro-2-imino-3,4-dihydrospiro[benzo[h]chromene-4,3'-indoline]-3-carbonitrile
  参考文献：
  名称：

  碘代苯二乙酸酯和N-氯代丁二酰亚胺中2-氨基-4 H-吡喃的氧化双官能化：反应性，机理见解和DFT计算

  摘要：

  用氨基乙酸碘代苯（IBD）和N-氯代琥珀酰亚胺（NCS）试剂可完成2-氨基-4 H-吡喃的氧化双官能化反应。2-氨基-4 H-吡喃在IBD中经历一个双胺基团的迁移（1a，b，2a – i，3a，b和4），而在NCS中，氯和烷氧基同时发生色烯双键（6a – i）。

  DOI：

  10.1021/jo301801b
• 作为产物：
  描述：

  2-(2-氧杂环丁-3-亚基)丙二腈 、 萘酚 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以85%的产率得到2-amino spiro[(4H)-benzo(h)chromen-4,3'-(3'H)-indol]-(1'H)-2'-one-3-carbonitrile
  参考文献：
  名称：

  NEW SPIROPYRAN-4-YLINDOLIDINE DERIVATIVES FROM THE REACTION OF 2-OXO-3-CYANOMETHYLIDENE-2,3-DIHYDROINDOLES WITH CYCLOHEXANEDIONES AND PHENOLS

  摘要：

  DOI：

  10.1080/00304949809355299

文献信息

• An efficient and practical synthesis of specially 2-amino-4H-pyrans catalyzed by C4(DABCO-SO3H)2·4Cl
  作者：Omid Goli-Jolodar、Frahad Shirini、Mohadeseh Seddighi

  DOI：10.1016/j.dyepig.2016.06.001

  日期：2016.10

  A mild, simple and convenient procedure for the synthesis of spiro-oxindole heterocycles containing fused 4H-pyran ring and also bis-2-amino-4H-pyrans derivatives was described using C4(DABCO-SO3H)2·4Cl as a nano, efficient, cheap, and reusable catalyst under mild and homogeneous conditions.

  使用C 4（DABCO-SO 3 H）2 · 4Cl描述了一种温和，简单，方便的方法，用于合成含有稠合的4 H-吡喃环以及双-2-氨基-4 H-吡喃衍生物的螺-羟吲哚杂环。在温和均匀的条件下作为一种纳米，高效，廉价且可重复使用的催化剂。
• Heterogeneous ditopic ZnFe₂O₄catalyzed synthesis of 4H-pyrans: further conversion to 1,4-DHPs and report of functional group interconversion from amide to ester
  作者：Paramita Das、Arghya Dutta、Asim Bhaumik、Chhanda Mukhopadhyay

  DOI：10.1039/c3gc42095g

  日期：——

  Highly stable, environmentally benign ZnFe2O4 nanopowder was prepared, characterized and applied in the one-pot, three-component synthesis of 4H-pyrans in water. The ZnFe2O4 catalyst provides both acidic (Fe3+) and basic functionalities (O2−) as the reaction requires. The advantages of this method lie in its simplicity, cost effectiveness, environmental friendliness and easier scaling up for large scale synthesis. Water was exploited both as a reaction medium as well as a medium for synthesis of the catalyst. Moreover, water was the only byproduct. The present report puts forward an application of 4H-pyrans for the synthesis of 1,4-DHPs. This is the first attempt towards the synthesis of 4H-pyran-3-carboxylate from 4H-pyran-3-carboxamide. The corresponding functional group interconversion from amide to ester is rare in organic synthesis.

  成功制备、表征并应用了一种稳定且对环境友好的ZnFe2O4纳米粉，在水相中实现了4H-吡喃的一锅法三组分合成。ZnFe2O4催化剂同时提供了反应所需的酸性（Fe3+）和碱性（O2−）功能。该方法的优势在于其简单性、成本效益、环境友好性以及更易于放大进行大规模合成。水既被用作反应介质，也被用作催化剂的合成介质。此外，水是唯一的副产品。本报告提出了一种应用4H-吡喃合成1,4-二氢吡啶（1,4-DHPs）的方法。这是首次尝试从4H-吡喃-3-甲酰胺合成4H-吡喃-3-羧酸酯。在有机合成中，从酰胺到酯的功能团转换是罕见的。
• 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。
• Synthesis of Quinolines, Spiro[4<i>H</i>-pyran-oxindoles] and Xanthenes Under Solvent-Free Conditions
  作者：Farzaneh Mohamadpour、Malek Taher Maghsoodlou、Mojtaba Lashkari、Reza Heydari、Nourallah Hazeri

  DOI：10.1080/00304948.2019.1653126

  日期：2019.9.3

  Green multi-component domino reactions (MCRs)1–7 for the synthesis of fine chemicals have attracted much recent interest.8–9 Quinolines, spiro[4H-pyran-oxindoles] and xanthenes are reported as havi...

  用于合成精细化学品的绿色多组分多米诺反应 (MCR)1-7 最近引起了广泛关注。8-9 喹啉、螺 [4H-吡喃-羟吲哚] 和呫吨据报道具有...
• Copper(II) acetate monohydrate: an efficient and eco-friendly catalyst for the one-pot multi-component synthesis of biologically active spiropyrans and 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives under solvent-free conditions
  作者：Farzaneh Mohamadpour、Malek Taher Maghsoodlou、Reza Heydari、Mojtaba Lashkari

  DOI：10.1007/s11164-016-2565-0

  日期：2016.12

  natural and economical catalyst for the multi-component efficient synthesis of biologically active spiro-4H-pyran derivatives and 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives with excellent yields and short reaction times. The most important advantages of this procedure are its mild, non-toxic and inexpensive catalyst, one-pot synthesis, environmentally benign nature, solvent-free conditions

  摘要 我们已经研究了乙酸铜（II）一水合物作为温和的，对环境无害的，天然的和经济的催化剂，用于多组分有效合成生物活性spiro-4 H -pyran衍生物和1 H -pyrazolo的催化能力[1,2] -b] phthalazine-5,10-dione衍生物，具有优异的收率和较短的反应时间。该方法最重要的优点是其温和，无毒且便宜的催化剂，一锅合成，环境友好的性质，无溶剂条件，简单的操作程序和高效的条件。 图形概要