ethyl 2-amino-7,7-dimethyl-2',5-dioxo-1',2',5,6,7,8-hexahydrospiro[chromene-4,3'-indole]-3-carboxylate | 336180-95-1

• 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-7,7-dimethyl-2',5-dioxo-1',2',5,6,7,8-hexahydrospiro[chromene-4,3'-indole]-3-carboxylate
• 英文别名: ethyl‑2‑amino‑7,7‑dimethyl‑2',5‑dioxo‑5,6,7,8‑tetrahydrospiro[chromene‑4,3'‑indoline]‑3‑carboxylate；ethyl 2-amino-7,7-dimethyl-2',5-dioxo-5, 6,7, 8-tetrahydrospiro[chromene-4,3-indoline]-3-carboxylate；ethyl 2-amino-7,7-dimethyl-2',5-dioxo-5,6,7,8-tetrahydro-spiro[chromene-4,3'-indoline]-3-carboxylate；ethyl 2-amino-7,7-dimethyl-2',5-dioxo-5,6,7,8-tetrahydrospiro[chromene-4,3'-indoline]-3-carboxylate；ethyl 2-amino-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydrospiro[chromene-4,3'-indole]-2'-one-3-carboxylate；ethyl-2-amino-7,7-dimethyl-2',5-dioxo-5,6,7,8-tetrahydrospiro[chromene-4,3'-indoline]-3-carboxylate；ethyl 2'-amino-7',7'-dimethyl-2,5'-dioxospiro[1H-indole-3,4'-6,8-dihydrochromene]-3'-carboxylate
• CAS: 336180-95-1
• 化学式: C₂₁H₂₂N₂O₅
• 分子量: 382.416
• InChiKey: HTPACFUSOPMHTM-UHFFFAOYSA-N

物化性质

• 熔点：
  263 °C (decomp)
• 沸点：
  633.2±55.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 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 2-(2-oxoindolin-3-ylidene)cyanoacetate 、 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， 以68%的产率得到ethyl 2-amino-7,7-dimethyl-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

• Synthesis of functionalized chromene and spirochromenes using l -proline-melamine as highly efficient and recyclable homogeneous catalyst at room temperature
  作者：Sakkani Nagaraju、Banoth Paplal、Kota Sathish、Santanab Giri、Dhurke Kashinath

  DOI：10.1016/j.tetlet.2017.09.060

  日期：2017.11

  commercially cheap l-proline and melamine for the synthesis of chromenes and spirochromenes (spirooxindoles) via multicomponent reactions at room temperature. Systematic studies were conducted in order to achieve desired reactivity and recyclability of the catalyst using various α-amino acids and aromatic amines as donor-acceptor pairs. Among the screened combinations, l-proline and melamine (3:1 ratio;

  使用便宜的1-脯氨酸和三聚氰胺开发了一种有效且可循环使用的均相催化剂，用于在室温下通过多组分反应合成色烯和螺环色酮（螺并辛多烯）。为了使用各种α-氨基酸和芳族胺作为供体-受体对，进行系统研究以实现所需的反应性和催化剂的可回收性。在筛选的组合中，l脯氨酸和三聚氰胺（3：1的比例；占总重量的3 mol％）被认为是最佳的催化剂，可以在室温下非常短的时间内（1-15分钟）以优异的产率（高达99％）提供所需的产品在DMSO中作为溶剂。通过添加EtOAc来回收催化剂，并且在不损失催化活性的情况下重复使用多达5个循环。
• 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。
• Nano-FGT: a green and sustainable catalyst for the synthesis of spirooxindoles in aqueous medium
  作者：Ramen Jamatia、Ajay Gupta、Amarta Kumar Pal

  DOI：10.1039/c5ra27552k

  日期：——

  glutathione grafted nano-organocatalyst (nano-FGT) was used as an efficient catalyst for the synthesis of spirooxindole derivatives. An aqueous medium, easy separation by an external magnet, efficient catalyst reusability, low catalyst loading, and column chromatography free separation of the product makes the present procedure green, sustainable and economically viable. The TON and TOF of the nanocatalyst

  谷胱甘肽接枝的纳米有机催化剂（nano-FGT）被用作合成螺恶英吲哚衍生物的有效催化剂。水性介质，易于被外部磁体分离，有效的催化剂可重复使用性，低的催化剂负载量以及产物的无柱色谱分离使本发明方法绿色，可持续且经济可行。纳米催化剂的TON和TOF分别达到850 000和56 667 min -1。