1-Methyl-3-(2-naphthalen-2-yl-2-oxoethylidene)indol-2-one | 1246666-79-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-Methyl-3-(2-naphthalen-2-yl-2-oxoethylidene)indol-2-one
• 英文别名: 1-methyl-3-(2-naphthalen-2-yl-2-oxoethylidene)indol-2-one
• CAS: 1246666-79-4
• 化学式: C₂₁H₁₅NO₂
• 分子量: 313.356
• InChiKey: XPBYSKLMIWRECP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  重氮乙酸乙酯 、 1-Methyl-3-(2-naphthalen-2-yl-2-oxoethylidene)indol-2-one 以 乙醇 、 乙腈 为溶剂， 以0.703 g的产率得到ethyl 2-(2-naphthoyl)-1'-methyl-2'-oxospiro[cyclopropane-1,3'-indoline]-3-carboxylate
  参考文献：
  名称：

  Highly diastereoselective synthesis of spiro[cyclopropane-1,3′-indolin]-2′-ones via catalyst-free cyclopropanation using ethyl diazoacetate

  摘要：

  Substituted 3-methyleneindolin-2-ones were efficiently cyclopropanated with ethyl diazoacetate to yield spiro[cyclopropane-1,3'-indolin]-2'-ones in a catalyst-free and highly diastereoselective reaction in a mixture of ethanol acetonitrile (1:1 v/v) as solvent. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.065

文献信息

• Asymmetric [3 + 2] Cycloaddition Reaction of Isatin-Derived MBH Carbonates with 3-Methyleneoxindoles: Enantioselective Synthesis of 3,3′-Cyclopentenyldispirooxindoles Incorporating Two Adjacent Quaternary Spirostereocenters
  作者：Yu Chen、Bao-Dong Cui、Yi Wang、Wen-Yong Han、Nan-Wei Wan、Mei Bai、Wei-Cheng Yuan、Yong-Zheng Chen

  DOI：10.1021/acs.joc.8b01506

  日期：2018.9.7

  A highly regio- and stereoselective [3 + 2] cycloaddition reaction for constructing novel 3,3′-cyclopentenyldispirooxindoles incorporating two adjacent quaternary spirostereocenters is reported. Under the mild conditions, the asymmetric annulation of isatin-derived MBH carbonates with 3-methyleneoxindoles involving a chiral tertiary amine catalyst provides the corresponding dispirooxindole frameworks

  报道了一种高度区域选择性和立体选择性的[3 + 2]环加成反应，用于构建结合了两个相邻的季螺中心的新型3,3'-环戊烯基二螺并氧杂吲哚。在温和的条件下，由靛红衍生的MBH碳酸酯与3-亚甲基吲哚的不对称环合涉及手性叔胺催化剂，为相应的双螺并恶唑骨架提供了极高的对映选择性控制能力。通过克规模的实验和所得产物的简单转化证明了该方法的进一步合成效用。此外，在控制实验的基础上，还提出了这种环化反应的合理机制。
• Brønsted Base and Lewis Acid Cooperatively Catalyzed Asymmetric <i>exo</i>′-Selective [3 + 2] Cycloaddition of Trifluoromethylated Azomethine Ylides and Methyleneindolinones
  作者：Yang Yi、Yuan-Zhao Hua、Hui-Jie Lu、Lan-Tao Liu、Min-Can Wang

  DOI：10.1021/acs.orglett.0c00283

  日期：2020.4.3

  3-dipolar cycloaddition is reported through chiral dinuclear zinc catalysts. An asymmetric exo′-selective [3 + 2] cycloaddition of CF3-containing N-unprotected isatin-derived azomethine ylides is realized. In the presence of 10 mol % of catalyst, azomethine ylides react efficiently with methyleneindolinones, giving a series of trifluoromethyl-substituted 2,3-pyrrolidinyl dispirooxindoles with highly enantio-

  通过手性双核锌催化剂报道了布朗斯台德碱和路易斯酸协同催化的1，3-偶极环加成反应。实现了含CF 3的N-未保护的，由靛红衍生的偶氮甲碱的不对称exo'-选择性[3 + 2]环加成。在10摩尔％的催化剂存在下，甲亚胺基团与亚甲基吲哚满酮有效反应，得到一系列三氟甲基取代的2,3-吡咯烷基二螺氧基辛酮，具有高对映体（ee高达99％）和exo'选择性（> 20： 1博士）。一步即可构建多达四个连续的立体生成中心，包括两个相邻的螺旋四元立体中心。
• Highly diastereoselective synthesis of spiro[cyclopropane-1,3′-indolin]-2′-ones via catalyst-free cyclopropanation using ethyl diazoacetate
  作者：Ram Awatar Maurya、Chada Narsimha Reddy、Geeta Sai Mani、Jeevak Sopanrao Kapure、Praveen Reddy Adiyala、Jagadeesh Babu Nanubolu、Kiran Kumar Singarapu、Ahmed Kamal

  DOI：10.1016/j.tet.2014.05.065

  日期：2014.8

  Substituted 3-methyleneindolin-2-ones were efficiently cyclopropanated with ethyl diazoacetate to yield spiro[cyclopropane-1,3'-indolin]-2'-ones in a catalyst-free and highly diastereoselective reaction in a mixture of ethanol acetonitrile (1:1 v/v) as solvent. (C) 2014 Elsevier Ltd. All rights reserved.