3-(6-甲氧基-1H-吲哚-3-基)-3-氧代丙腈 | 1082892-90-7

• 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
• 中文名称: 3-(6-甲氧基-1H-吲哚-3-基)-3-氧代丙腈
• 英文名称: 3-(6-methoxy-1H-indol-3-yl)-3-oxopropanenitrile
• CAS: 1082892-90-7
• 化学式: C₁₂H₁₀N₂O₂
• 分子量: 214.224
• InChiKey: DGSZFRCRLMDIEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(6-甲氧基-1H-吲哚-3-基)-3-氧代丙腈 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 4.0h， 以92%的产率得到3-乙酰基-6-甲氧基吲哚
  参考文献：
  名称：

  Novel and Simple Methodology for the Synthesis of 3-Acetylindoles and their N-Alkyl Derivatives Using TBAB as Phase Transfer Catalyst

  摘要：

  报道了一种利用5%氢氧化钠水溶液，将3-氰基乙酰基吲哚2(a-e)高效转化为3-乙酰基吲哚3(a-e)的简便方法。四丁基溴化铵（TBAB）被发现是一种有效的相转移催化剂，用于合成3-乙酰基吲哚3(a-e)的N-烷基衍生物5(a-t)，产率优异。2(a-e)本身是通过吲哚1(a-e)与氰基乙酸在丙酸酐存在下于100°C反应5-10分钟得到的。在热酸性条件下部分水解2(a-e)，得到相应的羧酰胺α-(3-吲哚羧酰基)乙酰胺4(a-e)，这些羧酰胺可以通过与5%氢氧化钠水溶液回流2-2.5小时，容易地转化为相应的3(a-e)。

  DOI：

  10.2174/157017811799304395
• 作为产物：
  描述：

  6-甲氧基吲哚 、 氰乙酸 在 丙酸酐 作用下， 生成 3-(6-甲氧基-1H-吲哚-3-基)-3-氧代丙腈
  参考文献：
  名称：

  Novel and Simple Methodology for the Synthesis of 3-Acetylindoles and their N-Alkyl Derivatives Using TBAB as Phase Transfer Catalyst

  摘要：

  报道了一种利用5%氢氧化钠水溶液，将3-氰基乙酰基吲哚2(a-e)高效转化为3-乙酰基吲哚3(a-e)的简便方法。四丁基溴化铵（TBAB）被发现是一种有效的相转移催化剂，用于合成3-乙酰基吲哚3(a-e)的N-烷基衍生物5(a-t)，产率优异。2(a-e)本身是通过吲哚1(a-e)与氰基乙酸在丙酸酐存在下于100°C反应5-10分钟得到的。在热酸性条件下部分水解2(a-e)，得到相应的羧酰胺α-(3-吲哚羧酰基)乙酰胺4(a-e)，这些羧酰胺可以通过与5%氢氧化钠水溶液回流2-2.5小时，容易地转化为相应的3(a-e)。

  DOI：

  10.2174/157017811799304395

文献信息

• Rhodium-catalyzed C2 and C4 C–H activation/annulation of 3-(1H-indol-3-yl)-3-oxopropanenitriles with internal alkynes: a facile access to substituted and fused carbazoles
  作者：Tao Zhou、Bin Li、Baiquan Wang

  DOI：10.1039/c7cc02808c

  日期：——

  annulation reactions of 3-(1H-indol-3-yl)-3-oxopropanenitriles with internal alkynes have been developed. A series of substituted carbazoles and 4H-oxepino[2,3,4,5-def]carbazoles, through a formal Rh(III)-catalyzed (4+2) cycloaddition with an alkyne and tandem (4+2) and (5+2) cycloaddition with two molecules of alkynes, were obtained. The reactions involved sequential cleavage of C(sp2)–H/C(sp3)–H bonds

  已经开发了铑催化的3-（1 H-吲哚-3-基）-3-氧代丙烷腈与内部炔烃的氧化环化反应。通过带有炔烃和串联（4 + 2）的正式Rh（III）催化的（4 + 2）环加成反应，生成一系列取代的咔唑和4 H -oxepino [2,3,4,5- def ]咔唑获得5 + 2）与两个炔烃分子的环加成。反应包括第一步中的C（sp 2）–H / C（sp 3）–H键的顺序裂解和炔烃的环化，以及C（sp 2）–H / O–H键的连续裂解和环化的顺序。第二步是与另一个炔烃 4 H -oxepino [2,3,4,5- def中的一些]咔唑产品在固态时表现出强烈的荧光。
• <scp>l</scp>-Proline-Catalyzed Knoevenagel Condensation: A Tandem Synthesis of 3-Acetylcoumarinoindoles and Their<i>N</i>-Alkyl Derivatives by Using PEG-600 as the Reaction Medium
  作者：M. Venkatanarayana、P. K. Dubey

  DOI：10.1002/jhet.1784

  日期：2014.7

  A tandem synthesis of 3‐acetylcoumarinoindoles 5a, 5b, 5c, 5d, 5e in the presence of catalytic amount of l‐proline in ethanol medium is reported. l‐proline has been utilized as an efficient and eco‐friendly catalyst for the Knoevenagel condensation of 3‐cyanoacetylindoles 1a, 1b, 1c, 1d, 1e with 2‐hydroxybenzaldehyde (2) to afford the corresponding substituted 3‐(1H‐indol‐3‐yl)2‐(2‐hydroxybenzylid

  据报道，在乙醇培养基中催化量的l-脯氨酸存在下，串联合成3-乙酰香豆素吲哚5a，5b，5c，5d，5e。l脯氨酸已被用作高效，环保的催化剂，用于3-氰基乙酰吲哚1a，1b，1c，1d，1e与2-羟基苯甲醛（2）的Knoevenagel缩合反应，从而提供相应的取代的3-（1 H-吲哚-3-基）2-（2-羟基亚苄基）-3-氧代丙烷腈3（a-e），未经隔离处理的则用热浓溶液处理。HCl可以高产率提供3-乙酰香豆素吲哚4a，4b，4c，4d，4e。随后，将它们与硫酸二甲酯在PEG-600（印度安得拉邦海得拉巴）作为高效绿色溶剂存在下反应，得到相应的N-甲基-3-乙酰香豆素吲哚5a，5b，5c，5d，5e。中等产量。
• Water Mediated One-Pot, Stepwise Green Synthesis, Anti-Inflammatory and Analgesic Activities of (3-Amino-1-Phenyl-1H-Benzo[f]Chromen-2-yl) (1H-Indol-3-yl) Methanone Catalysed by L-Proline
  作者：G. Ganga Reddy、Ch. Venkata Ramana Reddy、B. Srinivasa Reddy

  DOI：10.2174/1573406418666211224125310

  日期：2022.8

  The reactions were carried out by one pot three-component synthesis, 3- cyanoacetylindole (1) on reaction with aromatic aldehydes (2) and β-naphthol (3) in an aqueous medium in the presence of L-proline as a catalyst under reflux for 30 min, resulting in (3-amino-1- phenyl-1H-benzo[f]chromen-2-yl) (1H-indol-3-yl)methanone (4). The method has many advantages like short reaction times, good yields, and simple workup procedure, besides being green in nature. Pharmacological evaluation of title compounds was done for anti-inflammatory and analgesic activities. Anti-inflammatory activity was carried carrageenan-induced paw edema model in which indomethacin was used as standard and analgesic activity was evaluated by eddy's hot plate method using diclofenac as standard drug.

  Benzopyrans or chromenes are an important class of heterocyclic compounds due to their broad spectrum of biological activity and a wide range of applications in medicinal chemistry. The chromene moiety is found in various natural products with interesting biological properties. Chromenes constitute the basic backbone of various types of polyphenols and are widely found in alkaloids, tocopherols, flavonoids, and anthocyanins. Indoles are omnipresent in various bioactive compounds like alkaloids, agrochemicals, and pharmaceuticals.

  The objective of this study is to synthesize one-pot stepwise Green synthesis, antiinflammatory and analgesic activities of 3-amino-1-phenyl-1H-benzo[f]chromen-2-yl) (1H-indol-3- yl) methanones.

  The acute anti-inflammatory effect was evaluated by carrageenan-induced mice paw edema (Ma Rachchh et al., 2011). Edema was induced by injecting carrageenan (1% w/v, 0.1 ml) in the right hind paw of mice. The test compounds 1-12, indomethacin (10 mg/kg), and the vehicle were administered orally one hour before injection of carrageenan. Paw volume was measured with a digital plethysmometer at 0, 30, 60, 90, 120 min after injection. Percentage increase =A-B/ A *100

  Carrageenan induced paw edema model was used for anti-inflammatory activity in which animals treated with standard (indomethacin) and test compounds showed a significant decrease in the paw edema. Analgesic activity was estimated using Eddy’s hot plate method; animals were treated with standard (diclofenac) and test compounds showed a significant increase in the reaction time.

  A green, one-pot, step-wise and three-component synthesis of 3-amino-1-phenyl-1Hbenzo[ f]chromen-2-yl) (1H-indol-3-yl) methanone was achieved by using water as a solvent, Lproline as catalyst under reflux conditions. The reactions were carried out in eco-friendly conditions with shorter reaction times, easier workup, and high yields. Anti-inflammatory activity was evaluated by carrageenan-induced paw edema model, where significant anti-inflammatory activity is shown by all the test compounds 4(a-l) compared to standard drug. Analgesic activity was studied by Eddy’s Hot plate method and Test compounds 4e, 4f, 4h, 4i, 4j, 4k, 4l showed significant activities compared to the reference drug.

  目的：本研究的目的是通过一锅法三组分合成法合成3-氨基-1-苯基-1H-苯并[f]色烯-2-基）(1H-吲哚-3-基)甲酮，并评估其抗炎和镇痛活性。 背景：苯并吡喃或色烯是一类重要的杂环化合物，由于其广泛的生物活性和在医药化学中的广泛应用而备受关注。色烯基团在许多具有有趣生物学性质的天然产物中被发现。色烯是各种多酚类化合物的基本骨架，并广泛存在于生物碱、生育酚、黄酮类和花青素中。吲哚在各种生物活性化合物中广泛存在，如生物碱、农药和药物中。 方法：急性抗炎效应通过卡拉胶诱导小鼠足肿胀（Ma Rachchh等人，2011）评估。将卡拉胶（1％w/v，0.1ml）注射到小鼠的右后脚足底部引起水肿。在注射卡拉胶前一小时口服测试化合物1-12、吲哌灵（10mg/kg）和溶剂。注射后0、30、60、90、120分钟用数字式测量仪测量足肿胀体积。增加百分比= A-B / A * 100 结果：卡拉胶诱导的足肿胀模型用于评估抗炎活性，治疗标准（吲哌灵）和测试化合物显示出明显的减少足肿胀。利用Eddy's热板法评估镇痛活性；动物经过治疗标准（双氯芬酸）和测试化合物后，反应时间显著增加。 结论：通过使用水作为溶剂，L-脯氨酸作为催化剂，在回流条件下实现了3-氨基-1-苯基-1H-苯并[f]色烯-2-基）（1H-吲哚-3-基）甲酮的绿色、一锅法、逐步法和三组分合成。反应在环保条件下进行，反应时间短，易于操作，收率高。卡拉胶诱导的足肿胀模型评估了抗炎活性，所有测试化合物4（a-l）均表现出显著的抗炎活性，与标准药物相比。通过Eddy's热板法研究了镇痛活性，测试化合物4e、4f、4h、4i、4j、4k、4l与参考药物相比表现出显著的活性。
• Venkatanarayana; Dubey, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 6, p. 810 - 813
  作者：Venkatanarayana、Dubey

  DOI：——

  日期：——
• Novel and Simple Methodology for the Synthesis of 3-Acetylindoles and their N-Alkyl Derivatives Using TBAB as Phase Transfer Catalyst
  作者：M. Venkatanarayana、Pramod K. Dubey

  DOI：10.2174/157017811799304395

  日期：2011.11.1

  Using 5% aq. NaOH, a simple method for the transformation of 3-cyanoacetylindoles 2(a-e) into 3- acetylindoles 3 (a-e), in good yields, is reported. Tetrabutylammoniumbromide (TBAB) is found to be an efficient phase transfer catalyst for the synthesis of N-alkyl derivatives 5(a-t) of 3-acetylindoles 3(a-e) giving products in excellent yields. 2 (a-e) were themselves obtained from simple indoles 1 (a-e) by reaction with cyano acetic acid in the presence of propionic anhydride at 100 °C for 5-10 min. Partial hydrolysis of 2 (a-e) under hot acidic conditions yielded the corresponding carboxamides α-(3-indolecarboxoyl)acetamides 4(a-e). Which could be readily transformed into the respective 3(a-e) by refluxing with 5% aq. NaOH for 2-2.5 h.

  报道了一种利用5%氢氧化钠水溶液，将3-氰基乙酰基吲哚2(a-e)高效转化为3-乙酰基吲哚3(a-e)的简便方法。四丁基溴化铵（TBAB）被发现是一种有效的相转移催化剂，用于合成3-乙酰基吲哚3(a-e)的N-烷基衍生物5(a-t)，产率优异。2(a-e)本身是通过吲哚1(a-e)与氰基乙酸在丙酸酐存在下于100°C反应5-10分钟得到的。在热酸性条件下部分水解2(a-e)，得到相应的羧酰胺α-(3-吲哚羧酰基)乙酰胺4(a-e)，这些羧酰胺可以通过与5%氢氧化钠水溶液回流2-2.5小时，容易地转化为相应的3(a-e)。