(2-oxo-1,2-dihydro-1-methylindol-3-ylidene)acetic acid methyl ester | 61936-93-4

• 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: (2-oxo-1,2-dihydro-1-methylindol-3-ylidene)acetic acid methyl ester
• 英文别名: methyl 2-(1-methyl-2-oxoindolin-3-ylidene)acetate；Methyl 2-(1-methyl-2-oxo-indol-3-ylidene)acetate；methyl 2-(1-methyl-2-oxoindol-3-ylidene)acetate
• CAS: 61936-93-4
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: OOXDPAUCZFVVES-UHFFFAOYSA-N

物化性质

• 熔点：
  136-137 °C(Solv: methanol (67-56-1))
• 沸点：
  333.3±41.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-oxo-1,2-dihydro-1-methylindol-3-ylidene)acetic acid methyl ester 以 水 、 甲苯 为溶剂， 反应 36.0h， 生成 methyl 1′-methyl-2′-oxo-3-(trifluoromethyl)spiro[cyclopropane-1,3′-indoline]-2-carboxylate
  参考文献：
  名称：

  Synthesis of CF₃-Containing 3,3′-Cyclopropyl Spirooxindoles by Sequential [3 + 2] Cycloaddition/Ring Contraction of Ylideneoxindoles with 2,2,2-Trifluorodiazoethane

  摘要：

  A [3 + 2] cycloaddition/ring contraction sequence of ylideneoxindoles with in situ-generated 2,2,2-trifluorodiazoethane without the use of any transition-metal catalyst has been developed. The reaction provides efficient access to biologically important and synthetically useful CF3-containing 3,3'-cyclopropyl spirooxindoles in high yield (74-99%) with high diastereoselectivity (>95:5 d.r.).

  DOI：

  10.1021/jo500019a
• 作为产物：
  描述：

  靛红 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.59h， 生成 (2-oxo-1,2-dihydro-1-methylindol-3-ylidene)acetic acid methyl ester
  参考文献：
  名称：

  碱催化的3-亚硝基氧吲哚与O -Boc羟基氨基甲酸酯的可控反应，用于合成酰胺基丙烯酸酯和螺吡咯烷氧吲哚†

  摘要：

  已经开发了3-亚硝基氧吲哚与O -Boc羟基氨基甲酸酯的碱催化的发散反应，以提供通常通常高收率的各种酰胺基丙烯酸酯和螺并氮杂环丁烷氧吲哚的有效途径，这可能在药物发现中可能有用。

  DOI：

  10.1039/c6ob00891g

文献信息

• A Branched Domino Reaction: Asymmetric Organocatalytic Two-Component Four-Step Synthesis of Polyfunctionalized Cyclohexene Derivatives
  作者：Xiaofei Zeng、Qijian Ni、Gerhard Raabe、Dieter Enders

  DOI：10.1002/anie.201209581

  日期：2013.3.4

  Take two: By employing two equivalents of an aldehyde in an asymmetric organocatalytic domino reaction, the nucleophilic enamine intermediate is also converted into the corresponding iminium species through oxidation with o‐iodoxybenzoic acid. Thus, polyfunctionalized cyclohexene derivatives are formed from two simple starting materials in good yields and stereoselectivities (see scheme; Bn=benzyl

  采取两种：通过采用醛的两个当量的不对称有机催化反应多米诺，亲核烯胺中间体也与转化成相应的亚胺物种通过氧化ö -iodoxybenzoic酸。因此，多官能化的环己烯衍生物是由两种简单的起始原料形成的，具有良好的收率和立体选择性（参见方案； Bn =苄基，EWG =吸电子基团）。
• A novel and diastereoselective construction of H-pyrazolo[3,2-a]isoquinoline fused spirooxindoles via [3+2] cycloaddition
  作者：Panneerselvam Yuvaraj、Boreddy S.R. Reddy

  DOI：10.1016/j.tetlet.2013.11.116

  日期：2014.1

  A one-pot, highly efficient and diastereoselective construction of 1,2-dihyro-10′bH-spiro[indole-3,1′-pyrazole[3,2-a]isoquinoline]-2′-carboxylates via silver triflate-catalyzed [3+2] cycloaddition of N′-(2–alkynylbenzylidene)hydrazide with methyleneindolinones in good to excellent yield has been described. The transformation involves initially a condensation followed by 6-endo-intramolecular cyclization

  一锅，高效和非对映选择性的结构，通过三氟甲磺酸银，1,2-dihyro-10'b H-螺[吲哚-3,1'-吡唑[3,2-a]异喹啉] -2'-羧酸盐已经描述了N '-（2-炔基亚苄基）酰肼与亚甲基吲哚满酮催化的[3 + 2]环加成反应具有良好的收率。该转化首先涉及缩合，然后进行6-内-分子内环化形成偶极，然后与亚甲基吲哚满酮进行[3 + 2]-环加成，最后消除β-氢。
• Efficient synthesis of spiroisoxazoline oxindoles
  作者：Carlos J.A. Ribeiro、S. Praveen Kumar、Rui Moreira、Maria M.M. Santos

  DOI：10.1016/j.tetlet.2011.10.139

  日期：2012.1

  The synthesis of spiroisoxazoline oxindoles containing ester groups at position 4′ and aromatic or ester groups at position 3′ of the isoxazoline ring is reported. The compounds were synthesized in yields up to 94% by 1,3-dipolar cycloaddition of 3-methylene indolin-2-ones and chlorooximes in the presence of triethylamine or zinc.

  报道了在异恶唑啉环的位置4'处具有酯基并且在3'位置处具有芳族或酯基的螺异异唑啉恶吲哚的合成。在三乙胺或锌的存在下，通过3-亚甲基吲哚-2-酮和氯肟的1，3-偶极环加成合成化合物，产率高达94％。
• Pseudo-Five-Component Reaction for Diastereoselective Synthesis of Butterfly Shaped Bispiro[Oxindole-Pyrrolidine]s
  作者：Xiaofeng Zhang、Weiqi Qiu、Stephanie A. Murray、Desheng Zhan、Jason Evans、Jerry P. Jasinski、Xiao Wang、Wei Zhang

  DOI：10.1021/acs.joc.1c01797

  日期：2021.12.3

  A pseudo-five-component reaction involving double decarboxylative 1,3-dipolar cycloaddition of azomethine ylides with olefinic oxindoles for the diastereoselective synthesis of bispiro[oxindole-pyrrolidine]s is developed. The major diastereomers are unique butterfly shaped compounds with a plane of symmetry. Recyclable zeolite HY acid catalyst is used to promote the reaction, and only CO2 and H2O are

  拟五组分反应涉及偶氮甲亚胺叶立德与烯烃羟吲哚的双脱羧 1,3-偶极环加成反应，用于双螺环[羟吲哚-吡咯烷]的非对映选择性合成。主要的非对映异构体是具有对称平面的独特蝴蝶形化合物。采用可回收的沸石HY酸催化剂促进反应，仅产生CO 2和H 2 O副产物。
• <i>N</i>-Heterocyclic Carbene Catalytic [4 + 2] Cyclization of 3-Alkylenyloxindoles with Enals: γ-Carbon Activation for Enantioselective Assembly of Spirocarbocyclic Oxindoles
  作者：Hong Yao、Yu Zhou、Xia Chen、Pengfei Zhang、Jinyi Xu、Hong Liu

  DOI：10.1021/acs.joc.6b01596

  日期：2016.10.7

  ubiquitous structure of all-carbospirocyclic oxindoles makes the development of new methods for their enantioselective and stereoselective synthesis a significant ongoing challenge. Herein, we disclose a formal [4 + 2] annulation through N-heterocyclic carbene (NHC) catalysis for highly enantioselective synthesis of intriguing spirocarbocyclic oxindoles in the presence of Lewis acids. This protocol features

  全碳螺环氧吲哚的无处不在的结构使得开发其对映选择性和立体选择性合成的新方法成为一项重大的挑战。在本文中，我们公开了在路易斯酸存在下，通过N-杂环卡宾（NHC）催化进行的对映体选择性合成，其形式为[4 + 2] 。该方案的特点是在温和条件下具有良好的底物耐受性，良好的收率以及出色的非对映选择性和对映选择性（最高97％ee）。