| 1464140-93-9

• 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
• CAS: 1464140-93-9
• 化学式: C₂₃H₁₅ClFNO₂
• 分子量: 391.829
• InChiKey: KEYATHHZNQCHKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  在 哌啶 、 苯硫酚 作用下， 以 乙腈 为溶剂， 以66%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

• 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。
• 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。
• Synthesis of Dispirocyclopentyl-3,3′-bisoxindoles via Domino Cycloaddition Reactions of 4-Dimethylaminopyridinium Bromides with 3-Phenacylideneoxindoles
  作者：Lijuan Lu、Chaoguo Yan

  DOI：10.1002/cjoc.201500438

  日期：2015.10

  The base mediated cycloaddition reactions of 4‐dimethylamino‐1‐phenacylpyridinium bromides with two molecular 3‐phenacylideneoxindoles in methylene dichloride afforded functionalized dispirocyclopentyl‐3,3′‐bisoxindoles in good yields and with high diastereoselectivity. The similar cycloaddition reactions of 1‐(N,N‐dialkylcarbamoylmethyl) and 1‐cyanomethyl 4‐dimethylamino‐pyridinium bromide in refluxing

  在二氯甲烷中由碱介导的4-二甲氨基-1-苯并吡啶鎓溴化物与两个分子3-苯并亚苄基吲哚的环加成反应提供了高收率和高非对映选择性的功能化二螺环戊基-3,3'-双氧吲哚。在三乙胺存在下，在回流的乙醇中，1-（N，N-二烷基氨基甲酰基甲基）和1-氰基甲基4-二甲基氨基-吡啶溴的类似的环加成反应也导致具有高非对映选择性的二螺环戊基-3,3'-双氧吲哚。基于1 H NMR数据和单晶结构，阐明了双螺环戊基3,3'-双恶吲哚的立体化学。
• Synthesis spiro and fused chromenes via [4 + 2] cycloaddition of salicyl N-tosylimines and cyclic dienophiles
  作者：Xing Liu、Daqian Wang、Jing Sun、Chao-Guo Yan

  DOI：10.1016/j.molstruc.2024.137684

  日期：2024.5

  forward synthetic protocol for spiro and fused chromenes has been developed by base promoted oxa-Michael/Mannich reaction of salicyl N-tosylimines and various cyclic dienophiles. 1,4-diazabicyclo[2.2.2]octane (DABCO) promoted [4 + 2] cycloaddition reaction of salicyl N-tosylimines and 3-methyleneoxindoles or 2-arylidene-1,3-indanediones in THF at room temperature afforded functionalized spiro[chromane-3,3′-indolines]

  通过水杨酰 N-甲苯磺酰亚胺和各种环状嗜二烯烃的碱促进 oxa-Michael/Mannich 反应，开发了一种直接的螺和熔融铬合成方案。1,4-二氮杂双环[2.2.2]辛烷 （DABCO） 在室温下促进水杨基 N-甲苯磺酰亚胺和 3-亚甲基氧吲哚或 2-芳基-1,3-茚二酮在 THF 中的[4 + 2]环加成反应，得到功能化螺[色烷-3,3′-吲哚啉]或螺[chromane-3,2′-inden]-1′，3′-二酮，中等至良好产率和高非对映选择性。另一方面，水杨酰 N-甲苯磺酰亚胺和 5,6-未取代的 1,4-二氢吡啶的类似 [4 + 2] 环加成反应导致四氢铬基 [3,2-b] 吡啶衍生物的产率令人满意。
• Synthesis of dispirocyclopentyl-3,3′-bisoxindoles via base promoted cyclization reaction of 3-phenacylideneoxindoles with nitromethane
  作者：Li-Juan Lu、Chao-Guo Yan

  DOI：10.1016/j.tet.2014.11.028

  日期：2014.12

  A special kind of dispirocyclopentyl-3,3'-bisoxindoles, in which the two oxindole units exist at 1,2-positions of the newly formed cyclopentyl ring, were conveniently prepared in 49-86% yields by cyclization reaction of nitromethane with two molecules of 3-phenacylideneoxindoles in refluxing ethanol in the presence of DBU as base. The reaction has the advantages of readily available starting materials, operational simplicity, good yields, and high diastereoselectivity. (C) 2014 Elsevier Ltd. All rights reserved.