N-(1-benzyl-2-oxoindolin-3-yl)formamide | 1609356-85-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(1-benzyl-2-oxoindolin-3-yl)formamide
• 英文别名: N-(1-benzyl-2-oxoindol-3-yl)formamide；N-(1-benzyl-2-oxo-3H-indol-3-yl)formamide
• CAS: 1609356-85-5
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: SLQDFLGXZBLACT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-苯基-(4z)-(41-甲氧苯亚甲基)-5(4H)-恶唑酮 、 N-(1-benzyl-2-oxoindolin-3-yl)formamide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以89%的产率得到N-(1-benzyl-1′-formyl-3′-(4-methoxyphenyl)-2,5′-dioxospiro-[indoline-3,2′-pyrrolidin]-4′-yl)benzamide
  参考文献：
  名称：

  Tandem Michael Addition–Ring Transformation Reactions of 3-Hydroxyoxindoles/3-Aminooxindoles with Olefinic Azlactones: Direct Access to Structurally Diverse Spirocyclic Oxindoles

  摘要：

  An efficient method for the direct construction of two classes of spirocyclic oxindoles by the reactions of 3-hydroxyoxindoles/3-aminooxindoles and (Z)-olefinic azlactones through a tandem Michael addition-ring transformation process has been developed. With DBU as the catalyst, a range of spiro-butyrolactoneoxindoles and spiro-butyrolactamoxindoles, containing an oxygen or a nitrogen heteroatom, respectively, in the spiro stereocenter, were smoothly obtained with good to excellent diastereoselectivities in high yields.

  DOI：

  10.1021/jo500432c
• 作为产物：
  描述：

  3-amino-1-benzylindolin-2-one hydrochloride 、 甲酸乙酯 在 三乙胺 作用下， 反应 15.0h， 以67%的产率得到N-(1-benzyl-2-oxoindolin-3-yl)formamide
  参考文献：
  名称：

  Tandem Michael Addition–Ring Transformation Reactions of 3-Hydroxyoxindoles/3-Aminooxindoles with Olefinic Azlactones: Direct Access to Structurally Diverse Spirocyclic Oxindoles

  摘要：

  An efficient method for the direct construction of two classes of spirocyclic oxindoles by the reactions of 3-hydroxyoxindoles/3-aminooxindoles and (Z)-olefinic azlactones through a tandem Michael addition-ring transformation process has been developed. With DBU as the catalyst, a range of spiro-butyrolactoneoxindoles and spiro-butyrolactamoxindoles, containing an oxygen or a nitrogen heteroatom, respectively, in the spiro stereocenter, were smoothly obtained with good to excellent diastereoselectivities in high yields.

  DOI：

  10.1021/jo500432c

文献信息

• Organocatalytic Enantioselective Michael/Cyclization Domino Reaction between 3-Amideoxindoles and α,β-Unsaturated Aldehydes: One-Pot Preparation of Chiral Spirocyclic Oxindole-γ-lactams
  作者：Peng Yang、Xiao Wang、Feng Chen、Zheng-Bing Zhang、Chao Chen、Lin Peng、Li-Xin Wang

  DOI：10.1021/acs.joc.6b03090

  日期：2017.4.7

  enantioselective Michael/cyclization domino reaction between 3-amideoxindoles and α,β-unsaturated aldehydes is described. After sequential oxidation with pyridinium chlorochromate, a direct and one-pot preparation of highly sterically hindered spirocyclic oxindole-γ-lactams was achieved in 51–81% yields with 75–97% ee and ≤80/20 dr.

  描述了3-酰胺基吲哚与α，β-不饱和醛之间的第一有机催化对映选择性迈克尔/环化多米诺反应。用氯铬酸吡啶鎓进行顺序氧化后，可以直接和一锅制备高度受阻的螺环氧吲哚-γ-内酰胺，收率51-81％，ee为75-97％，dr≤80/ 20。
• Construction of bridged cyclic <i>N</i>,<i>O</i>-ketal spirooxindoles through a Michael addition/<i>N</i>,<i>O</i>-ketalization sequence
  作者：Yanshuo Zhu、Jia Guo、Shaojing Jin、Jiaomei Guo、Xuguan Bai、Qilin Wang、Zhanwei Bu

  DOI：10.1039/c8ob00306h

  日期：——

  The first highly diastereoselective TfOH-catalyzed Michael addition/N,O-ketalization sequence of 3-aminooxindoles and ortho-hydroxychalcones was achieved, delivering a wide range of bridged cyclic N,O-ketal spirooxindoles with complex and strained structures in 41–97% yields. Moreover, a gram-scale experiment and some chemical conversions were conducted to further demonstrate the synthetic value.

  实现了第一个高度非对映选择性的TfOH催化的3-氨基氧吲哚和邻羟基查耳酮的Michael加成/ N，O-缩酮化序列，提供了41–97％的具有复杂和应变结构的桥联环状N，O-缩酮螺硫醇。产量。此外，进行了克级实验和一些化学转化，以进一步证明合成值。
• An enantioselective synthesis of spiro-oxindole-based 3,4-dihydropyrroles via a Michael/cyclization cascade of 3-aminooxindoles with 2-enoylpyridines
  作者：Baodong Cui、Yu Chen、Jing Shan、Lei Qin、Changlun Yuan、Yi Wang、Wenyong Han、Nanwei Wan、Yongzheng Chen

  DOI：10.1039/c7ob02138k

  日期：——

  concentrated hydrochloric acid provided a wide range of chiral 3',4'-dihydrospiro[indoline-3,2'-pyrrol]-2-ones, bearing two adjacent tri- and tetrasubstituted stereocenters, in moderate to good yields with overall excellent stereoselectivities. The synthetic application of this methodology was presented by the scale-up experiment and transformation of product 5a into the spiro-oxindole-based pyrrolidines

  已经实现了3-氨基氧吲哚与2-烯丙基吡啶的有机催化和高度非对映和对映选择性反应，用于合成手性螺[吡咯烷烃-3，2'-氧吲哚]衍生物。使用基于辛可尼定的硫脲催化剂，3-氨基氧吲哚与2-烯丙基吡啶的不对称迈克尔/环化反应顺序，然后用浓盐酸进行脱水和脱保护，提供了广泛的手性3'，4'-二氢螺[indoline-3 ，[2'-吡咯] -2-酮带有两个相邻的三和四取代的立体中心，具有中等至良好的产率，总体上具有出色的立体选择性。该方法的合成应用是通过放大实验和将产品5a转化为基于螺-氧吲哚的吡咯烷6提出的。此外，还提出了该级联反应序列的合理过渡态。这项工作将提供一种新的方法来获取手性螺[pyrrolidin-3,2'-oxindole]衍生物。
• Organocatalytic Asymmetric Michael/Cyclization Cascade Reactions of 3-Hydroxyoxindoles/3-Aminooxindoles with α,β-Unsaturated Acyl Phosphonates for the Construction of Spirocyclic Oxindole-γ-lactones/lactams
  作者：Lin Chen、Zhi-Jun Wu、Ming-Liang Zhang、Deng-Feng Yue、Xiao-Mei Zhang、Xiao-Ying Xu、Wei-Cheng Yuan

  DOI：10.1021/acs.joc.5b02253

  日期：2015.12.18

  Enantioselective Michael/cyclization cascade reactions of 3-hydroxyoxindoles/3-aminooxindoles with α,β-unsaturated acyl phosphonates by using a cinchonine derived squaramide as the catalyst were developed. A broad range of spirocyclic oxindole-γ-lactones/lactams could be obtained in moderate to excellent yields (up to 98%) with good to excellent diastereo- and enantioselectivities (up to >99:1 dr and

  以辛可宁衍生的方酰胺为催化剂，开发了3-羟基氧吲哚/ 3-氨基氧吲哚与α，β-不饱和酰基膦酸酯的对映选择性迈克尔/环化级联反应。在温和条件下，可以以中等至优异的收率（高达98％）获得良好的非对映和对映选择性（高达> 99：1 dr和97％ee）的各种螺环羟吲哚-γ-内酯/内酰胺类化合物。 。这项工作代表了有关α，β-不饱和酰基膦酸酯用于螺环羟吲哚的不对称结构的第一个例子。
• 一种紫杉醇侧链苯基异丝氨酸衍生物及其制 备方法及应用
  申请人：贵州大学

  公开号：CN105037243B

  公开（公告）日：2017-09-05

  本发明公开了一种紫杉醇侧链苯基异丝氨酸衍生物及其制备方法及应用，本发明相应的3‑酰胺取代氧化吲哚与乙醛酸酯在碱性催化剂条件下，在有机溶剂中进行Aldol反应，获得3‑氨基‑α‑羟基‑β‑酯基‑3‑季碳氧化吲哚类化合物，该化合物可以作为紫杉醇侧链苯基异丝氨酸新型衍生物，合成新型紫杉醇侧链苯基异丝氨酸衍生物，该衍生物可以作为新型紫杉醇化合物合成的中间体，对药物的筛选和制药行业具有重要的应用价值，本发明针对这些衍生物对二种肿瘤细胞株如人肺癌细胞（A549）以及人白血病细胞（K562）所进行的肿瘤生长抑制活性筛选。