5-chloro-3-(2-oxo-2-(p-tolyl)ethylidene)indolin-2-one | 1397285-84-5

• 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: 5-chloro-3-(2-oxo-2-(p-tolyl)ethylidene)indolin-2-one
• 英文别名: 4-methylphenacylidene-5-chlorooxindole；5-chloro-3-[2-(4-methylphenyl)-2-oxoethylidene]-1H-indol-2-one
• CAS: 1397285-84-5
• 化学式: C₁₇H₁₂ClNO₂
• 分子量: 297.741
• InChiKey: OEXVDWTWOAAYSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-chloro-3-(2-oxo-2-(p-tolyl)ethylidene)indolin-2-one 在 哌啶 、 4-氯苯硫酚 作用下， 以 乙腈 为溶剂， 以55%的产率得到
  参考文献：
  名称：

  Construction of Dispirocyclopentanebisoxindoles via Self-Domino Michael-Aldol Reactions of 3-Phenacylideneoxindoles

  摘要：

  A simple protocol for the construction of novel dispirocyclopentanebisoxindoles is accomplished by the base promoted domino reactions between two molecules of 3-phenacylideneoxindoles with the participation of solvents, alcohol, or other added nucleophiles such as amines or thiophenols. Significantly, this domino reaction results in the complex dispiro compounds with high yields and diastereoselectivity, which would allow construction of dispirocyclopentanebisoxindole with four and five diastereoisomeric centers using simple materials.

  DOI：

  10.1021/jo4010603

文献信息

• Molecular diversity of the cyclization reaction of 3-methyleneoxindoles with 2-(3,4-dihydronaphthalen-1(2H)-ylidene)malononitriles
  作者：Yu-Ling Lu、Jing Sun、Ya-Jing Xie、Chao-Guo Yan

  DOI：10.1039/c6ra00476h

  日期：——

  The cyclization reaction of 3-methyleneoxindoles with 2-(3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile in ethanol in the presence of DBU at room temperature afforded functionalized 3′-iminospiro[indoline-3,2′-phenanthrenes] in good yields. However, the similar reaction of ethyl 2-cyano-2-(3,4-dihydronaphthalen-1(2H)-ylidene)acetate resulted in functionalized 3-oxospiro[indoline-3,2′-phenanthrenes]

  在室温下，在DBU存在下，3-亚甲基吲哚与2-（3,4-二氢萘-1（2 H）-亚烷基）丙二腈在乙醇中的环化反应提供了功能化的3'-亚氨基螺[吲哚啉-3,2'-菲]。然而，乙基2-氰基-2-（3,4-二氢萘-1（2 H）-亚烷基）乙酸酯的相似反应导致官能化的3-氧螺环[吲哚啉-3,2'-菲]和苯并[ d ]菲咯[2,3- f ] [1,3]二氮杂ze取决于底物的结构。此外，3-苯乙叉基亚吲哚与乙基2-氰基-2-（3,4-二氢萘-1（2 H）的环加成反应）-亚烷基）乙酸酯产生螺[吲哚啉-3,2'-菲] -4'-腈衍生物。通过1 H NMR数据和14个单晶结构清楚地阐明了环螺硫辛多环的立体化学。
• Diastereoselective synthesis of dispirooxindoles <i>via</i> [3+2] cycloaddition of azomethine ylides to 3-phenacylideneoxindoles and evaluation of their cytotoxicity
  作者：Ying Huang、Yi-Xin Huang、Jing Sun、Chao-Guo Yan

  DOI：10.1039/c8ra04375b

  日期：——

  structures indicated the reaction has high regioselectivity and diastereoselectivity. Furthermore, their biological activities have been preliminarily demonstrated by in vitro evaluation against mouse breast cancer cells 4T1 and human liver cancer cells HepG2 by MTT assay. The results demonstrated that some of the compounds showed cytotoxicities to cell lines of 4T1 and HepG2, and indicated that novel spirooxindoles

  1,2,3,4-四氢异喹啉、靛红和3-亚苯肟吲哚在回流乙醇中进行三组分反应，得到二螺[二氢吲哚-3,1'-吡咯并[2,1 -a ]异喹啉-3',3'-二氢吲哚] ( 4a–4x )通过原位生成的偶氮甲碱叶立德与 3-phenacylideneoxindoles 的环外双键进行 1,3-偶极环加成，获得良好的产率。 1 H NMR谱和单晶结构表明该反应具有较高的区域选择性和非对映选择性。此外，通过MTT法对小鼠乳腺癌细胞4T1和人肝癌细胞HepG2进行体外评价，初步证明了它们的生物学活性。结果表明，一些化合物对4T1和HepG2细胞系表现出细胞毒性，并表明新型螺吲哚可能成为潜在的先导化合物，用于进一步对其医学应用进行生物筛选。
• Additive-Free Three-Component Synthesis of Spiro-isoxazolidine-oxindoles Employing Trifluorodiazoethane
  作者：Ekta Gupta、Sindoori R. Nair、Ruchir Kant、Kishor Mohanan

  DOI：10.1021/acs.joc.8b02504

  日期：2018.12.7

  three-component protocol for the synthesis of trifluoromethylated spiro-isoxazolidine-oxindoles has been developed. This approach employs the 1,3-dipolar cycloaddition of trifluoromethyl nitrone, generated in situ from trifluorodiazoethane and nitrosoarene, with phenacylideneoxindoles. A range of phenacyclideneoxindoles and nitrosoarenes can be subjected to this reaction to generate the spiro-isoxazolidine-oxindole

  已经开发出一种有效的三组分方案，用于合成三氟甲基化的螺-异恶唑烷-羟吲哚。该方法采用了由三氟重氮乙烷和亚硝基芳烃与苯乙叉基氧吲哚原位生成的三氟甲基硝基的1,3-偶极环加成反应。可以使一定范围的苯并亚环己氧基吲哚和亚硝基芳烃进行该反应以生成螺-异恶唑烷-氧吲哚衍生物。进行的异恶唑烷的还原性开环反应证明了我们策略的合成潜力，导致了有趣的重排，从而生成了吡咯并喹啉衍生物。
• Convenient synthesis of functionalized spiro[indoline-3,2′-pyrrolizines] or spiro[indoline-3,3′-pyrrolidines] via multicomponent reactions
  作者：Jing Sun、Liang Chen、Hui Gong、Chao-Guo Yan

  DOI：10.1039/c5ob00437c

  日期：——

  three-component reaction of secondary α-amino acids including proline, sarcosine, thiazolidine-4-carboxylic acid with dialkyl acetylenedicarboxylate and 3-methyleneoxindoles in refluxing ethanol afforded the functionalized spiro[indoline-3,2′-pyrrolizines], spiro[indoline-3,3′-pyrrolidines] and spiro[indoline-3,6′-pyrrolo[1,2-c]thiazoles] in good yields and with high diastereoselectivity. Furthermore, similar multicomponent

  成功建立了一种新型原位甲亚胺叶立德及其相继的1，3-偶极环加成反应的一般可行路线。脯氨酸，肌氨酸，噻唑烷-4-羧酸等二级α-氨基酸与乙炔二羧酸二烷基酯和3-亚甲基吲哚在回流的乙醇中进行三组分反应，得到官能化的螺[吲哚啉-3,2'-吡咯啉]，螺[吲哚啉] -3,3'-吡咯烷]和螺[吲哚啉-3,6'-吡咯并[1,2- c ]噻唑]的收率高，非对映选择性高。此外，使用伯α-氨基酸（例如甘氨酸，丙氨酸和苯丙氨酸）进行的类似多组分反应产生了相应的（螺[吲哚啉-3,3'-吡咯烷] -1'-基）马来酸酯。
• Molecular diversity of cycloaddition reactions of the functionalized pyridinium salts with 3-phenacylideneoxindoles
  作者：Qin Fu、Chao-Guo Yan

  DOI：10.1016/j.tet.2013.05.034

  日期：2013.7

  cycloaddition reactions of a series of functionalized pyridinium salts, which were generated from reaction of pyridine with active alkyl halides such as p-nitrobenzyl bromide, N,N-diethyl chloroacetamide and phenacyl bromides with 3-phenacylideneoxindoles in the presence of triethylamine showed very interesting molecular diversities. A series of the functionalized spiro[cyclopropane-1,3′-indolines], and 3-

  在三乙胺的存在下，吡啶与活性烷基卤化物（如对硝基苄基溴，N，N-二乙基氯乙酰胺和苯甲酰溴与3-苯乙叉基氧吲哚）反应生成的一系列官能化吡啶鎓盐的环加成反应显示出非常有趣的结果。分子多样性。根据吡啶鎓盐的结构和反应条件，成功制备了一系列官能化的螺[环丙烷-1,3'-二氢吲哚]和3-呋喃-3（2 H）-亚烷基）吲哚-2-酮。简要讨论了反应的区域选择性和立体选择性以及反应机理。