| 1464140-82-6

• 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: 1464140-82-6
• 化学式: C₂₁H₂₀FNO₃
• 分子量: 353.393
• InChiKey: KGAPFFCKTXOHES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  在 tris(2,2′-bipyridyl)dichlororuthenium(II) hexahydrate 作用下， 以 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 以85%的产率得到1,1''-dibutyl-5,5''-difluoro-3',4'-bis(4-methoxybenzoyl)dispiro[indoline-3,1'-cyclobutane-2',3''-indoline]-2,2''-dione
  参考文献：
  名称：

  Diastereoselective synthesis of dispiro[indoline-3,1′-cyclobutane-2′,3″-indolines] via visible light catalyzed cyclodimerization of 3-phenacylideneoxindoles

  摘要：

  一个简单的合成方案已经开发出来，用于高对映选择性地合成具有功能化的二螺杂环[吲哚啉-3,1′-环丁烷-2′,3″-吲哚啉]。该反应通过3-苯乙酰亚胺吲哚酮的环二聚反应进行，在光敏催化剂Ru(bpy₃)Cl₂和可见光的存在下进行。

  DOI：

  10.1515/hc-2016-0022

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。
• Unprecedented formation of 2-oxaspiro[bicyclo[2.2.1]heptane-6,3′-indoline] derivatives from reaction of 3-phenacyalideneoxindole with malononitrile or ethyl cyanoacetate
  作者：Ya-Jing Xie、Jing Sun、Chao-Guo Yan

  DOI：10.1039/c4ra06272h

  日期：——

  3′-indoline] derivatives in good yields. Under similar reaction conditions, the reaction of cyanoacetamide with 3-phencylideneoxindoles resulted in polysubstituted 4-(2-oxoindolin-3-yl)-2-oxopyrrolidines. The stereochemistry of the reaction was well established by data from 1H NMR spectra and single crystal structures and a plausible reaction mechanism is rationally proposed.

  在哌啶存在下，丙二腈或氰基乙酸乙酯与两分子的3-苯二甲撑吲哚在乙醇中在室温下反应，得到新的7-（1-苄基-2-氧代吲哚-3-基）-2'-氧代-2-氧aspiro [双环[2.2.1]庚烷-6,3'-二氢吲哚]衍生物收率高。在相似的反应条件下，氰基乙酰胺与3-苯并二恶英吲哚的反应产生多取代的4-（2-氧代吲哚-3-基）-氧代吡咯烷。通过1 H NMR光谱和单晶结构的数据可以很好地确定反应的立体化学，并合理地提出了合理的反应机理。
• A Three-Component Reaction for the Efficient Construction of the 2′,11b′-Dihydrospiro[indoline-3,1′-pyrido[2,1-a]isoquinoline] Skeleton
  作者：Jing Sun、Yan Sun、Hui Gong、Chao-Guo Yan

  DOI：10.1002/jhet.2140

  日期：2015.9

  The three‐component reactions of isoquinoline, acetylenedicarboxylates, and 3‐phenacylideneoxindoles in ethanol at room temperature resulted in a mixture of two diastereoisomers of 2′,11b′‐dihydrospiro[indoline‐3,1′‐pyrido[2,1‐a]isoquinoline] derivatives, which were successfully separated and characterized. The regioselectivity and diastereoselectivity of this reaction were briefly discussed.

  在室温下，乙醇中异喹啉，炔二羧酸酯和3-苯二甲叉基吲哚的三组分反应导致2'，11b'-二氢螺[吲哚啉-3,1'-吡啶基[2,1-a]的两种非对映异构体的混合物异喹啉]衍生物，已成功分离和表征。简要讨论了该反应的区域选择性和非对映选择性。
• Construction of Dispirocyclopentanebisoxindoles via Self-Domino Michael-Aldol Reactions of 3-Phenacylideneoxindoles
  作者：Jing Sun、Ya-Jing Xie、Chao-Guo Yan

  DOI：10.1021/jo4010603

  日期：2013.9.6

  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.
• Domino Reactions of Vinyl Malononitriles with 3-Phenacylideneoxindoles for Efficient Synthesis of Functionalized Spirocyclic Oxindoles
  作者：Ya-Jing Xie、Jing Sun、Chao-Guo Yan

  DOI：10.1021/co500006c

  日期：2014.6.9

  The reactions of vinyl malononitriles with 3-phenacylideneoxindoles in ethanol in the presence of DBU as base resulted in the functionalized spirocyclic oxindoles through the domino Michael addition and intramolecular nucleophilic addition to cyano group. On the other hand, the similar reaction in the presence of piperidine as base afforded the simple Michael addition products in good yields. The stereochemistry of the spirocodndoles was established with H-1 NMR data and single crystal structures.