1-benzyl-5-chloro-3-(2-(4-methoxyphenyl)-2-oxoethylidene)indolin-2-one | 1464140-84-8

• 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: 1-benzyl-5-chloro-3-(2-(4-methoxyphenyl)-2-oxoethylidene)indolin-2-one
• CAS: 1464140-84-8
• 化学式: C₂₄H₁₈ClNO₃
• 分子量: 403.865
• InChiKey: QIVLDKNXKCPVFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-benzyl-5-chloro-3-(2-(4-methoxyphenyl)-2-oxoethylidene)indolin-2-one 在 哌啶 、 苯硫酚 作用下， 以 乙腈 为溶剂， 以79%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

• Indium chloride catalyzed three-component reaction for the synthesis of 2-((oxoindolin-3-yl)-4,5,6,7-tetrahydro-1H-indol-1-yl)benzamides
  作者：Yan-Hong Jiang、Chao-Guo Yan

  DOI：10.1039/c6ra08811b

  日期：——

  In the presence of indium chloride as a Lewis acid catalyst, the three-component reaction of benzohydrazide, cyclic diketones and 3-phenacylideneoxindoles in refluxing acetonitrile afforded functionalized 2-((oxoindolin-3-yl)-4,5,6,7-tetrahydro-1H-indol-1-yl)benzamides in satisfactory yields. Under similar conditions, the reaction with 2-hydroxybenzohydrazide and picolinohydrazide also resulted in

  在氯化铟作为路易斯酸催化剂的存在下，苯甲酰肼，环状二酮和3-苯并亚甲基吲哚在回流的乙腈中进行三组分反应，得到官能化的2-（（氧代吲哚-3-基）-4,5,6,7-四氢-1 H-吲哚-1-基）苯甲酰胺，收率令人满意。在相似的条件下，与2-羟基苯并肼和吡啶并酰肼的反应也导致相应的官能化的2-（（氧代吲哚-3-基）-4,5,6,7-四氢-1 H-吲哚-1-基）苯甲酰胺产量。的1 H和13 C NMR谱表明，在两者酮式和烯醇式存在得到的产物。
• TfOH-Catalyzed One-Pot Domino Reaction for Diastereoselective Synthesis of Polysubstituted Tetrahydrospiro[carbazole-1,3′-indoline]s
  作者：Ren-Yin Yang、Jing Sun、Yao Tao、Qiu Sun、Chao-Guo Yan

  DOI：10.1021/acs.joc.7b02397

  日期：2017.12.15

  one-pot sequential reaction of indoles, acetophenones (cyclic ketones), and various 3-methyleneoxindolines in toluene afforded polysubstituted tetrahydrospiro[carbazole-1,3′-indoline]s in satisfactory yields. 1H NMR spectra and single-crystal structures indicated that the obtained tetrahydrospiro[carbazole-1,3′-indoline]s existing in an unusual trans-configuration. The reaction mechanism was believed

  TfOH催化的吲哚，苯乙酮（环酮）和各种3-亚甲基二氢吲哚在甲苯中的一锅顺序反应可得到令人满意的多取代四氢螺环[咔唑-1,3'-二氢吲哚] s。1 H NMR谱和单晶结构表明，所获得的四氢螺[[咔唑-1,3'-二氢吲哚]以不寻常的反式构型存在。据认为，该反应机理是通过吲哚与苯乙酮的吲哚的多核苷酸催化3-烯基化，3-烯基吲哚与3-亚甲基二氧吲哚的狄尔斯-阿尔德反应以及酸催化的非对映异构化过程来进行的。
• Molecular diversity of TEMPO-mediated cycloaddition of ketohydrazones and 3-phenacylideneoxindoles
  作者：Rong Ye、Jing Sun、Ying Han、Chao-Guo Yan

  DOI：10.1039/d0nj06036d

  日期：——

  aza-Diels–Alder reaction of the in situ generated 1,2-diaza-1,3-diene. The reactions with 2-(2-phenylethylidene)-1-arylhydrazines in dioxane afforded functionalized spiro[indoline-3,3′-pyrazoles] though a [3+2] cycloaddition reaction of the in situ generated 1,3-dipolar azomethine imine. On the other hand, a similar reaction in acetonitrile unusually resulted in pyrazole derivatives via sequential [3+2]

  TEMPO根据化学结构和反应条件，促进了不同种类的酮hydr或醛hydr与3-苯并亚甲基吲哚的环加成反应，显示出非常有趣的分子多样性。在80°C下与1-（3,4-二氢萘-1-亚甲基）-2-芳基肼或1-环己基-2-芳基肼在乙腈中的反应提供官能化的螺[苯并[ h ] cinnoline-3,3'-二氢吲哚]或螺[cinnoline-3,3'-二氢吲哚]通过原位生成的1,2-二氮杂-1,3-二烯的aza-Diels-Alder反应。通过原位的[3 + 2]环加成反应，在二恶烷中与2-（2-苯基亚乙基）-1-芳基肼的反应提供了官能化的螺[吲哚啉-3,3'-吡唑]生成1,3-偶极偶氮甲亚胺。另一方面，乙腈中的类似反应通过顺序的[3 + 2]环加成和开环过程异常生成吡唑衍生物。
• Three-Component Reaction for the Convenient Synthesis of Functionalized 3-{1-[2-(1H-Indol-3-yl)ethyl]-4,5,6,7-tetrahydro-1H-indol-3-yl}indolin-2-ones
  作者：Chao-Guo Yan、Yan-Hong Jiang

  DOI：10.1055/s-0035-1561457

  日期：——

  efficient synthesis of functionalized 3-1-[2-(1H-indol-3-yl)ethyl]-4,5,6,7-tetrahydro-1H-indol-3-yl}indolin-2-ones in high yield via three-component reaction of tryptamine, dimedone, and 3-phenacylideneoxindoles in refluxing acetonitrile with p-toluenesulfonic acid as catalyst. A simple synthetic protocol was developed for the efficient synthesis of functionalized 3-1-[2-(1H-indol-3-yl)ethyl]-4,5,6

  摘要 为有效合成功能化的3- 1- [2-（1 H-吲哚-3-基）乙基] -4,5,6,7-四氢-1 H-吲哚-3-开发了一种简单的合成方案在对乙磺酸为催化剂的回流乙腈中，色胺，二甲酮和3-苯二甲叉基吲哚的三组分反应可高收率地得到}}吲哚啉-2-酮。 为有效合成功能化的3- 1- [2-（1 H-吲哚-3-基）乙基] -4,5,6,7-四氢-1 H-吲哚-3-开发了一种简单的合成方案在对乙磺酸为催化剂的回流乙腈中，色胺，二甲酮和3-苯二甲叉基吲哚的三组分反应可高收率地得到}}吲哚啉-2-酮。
• Synthesis of 7′-Arylidenespiro[indoline-3,1′-pyrrolizines] and 7′-Arylidenespiro[indene-2,1′-pyrrolizines] via [3 + 2] Cycloaddition and β-C–H Functionalized Pyrrolidine
  作者：Ying Huang、Hui-Lin Fang、Yi-Xin Huang、Jing Sun、Chao-Guo Yan

  DOI：10.1021/acs.joc.9b01920

  日期：2019.10.4

  three-component reaction of pyrrolidine, aromatic aldehydes, and 3-arylideneoxindolin-2-ones in refluxing toluene afforded functionalized 7'-arylidenespiro[indoline-3,1'-pyrrolizines] in good yields and with high diastereoselectivity. The similar three-component reaction with 2-arylidene-1,3-indanediones also gave 7'-arylidenespiro[indene-2,1'-pyrrolizines] in good yields. However, the reaction with 3-ph

  乙酸在回流的甲苯中催化吡咯烷，芳族醛和3-芳基氧杂吲哚-2-酮的三组分反应，可提供高收率和高非对映选择性的功能化7'-芳基螺[吲哚啉-3,1'-吡咯烷酮]。与2-亚芳基-1，3-茚满二酮的相似的三组分反应也以良好的产率得到了7'-亚芳基螺[茚-2,1'-吡咯烷酮]。然而，与3-苯乙叉基亚吲哚的反应以中等收率产生了螺[吲哚啉-3,1'-吡咯嗪]和7'-亚芳基取代的螺氧并吲哚的混合物。反应机理包括偶氮甲亚胺的生成，吡咯烷的β-CH官能化以及连续的[3 + 2]环加成反应。