2-(6-Bromo-1-methyl-2-oxoindol-3-ylidene)propanedinitrile | 1346253-56-2

• 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-(6-Bromo-1-methyl-2-oxoindol-3-ylidene)propanedinitrile
• 英文别名: 2-(6-bromo-1-methyl-2-oxoindol-3-ylidene)propanedinitrile
• CAS: 1346253-56-2
• 化学式: C₁₂H₆BrN₃O
• 分子量: 288.103
• InChiKey: HMTQRKNGGKJNPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(6-Bromo-1-methyl-2-oxoindol-3-ylidene)propanedinitrile 在 吗啉 、 N-((1S,2S)-2-(3-((1R)-(6-methoxyquinolin-4-yl)((2R,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thioureido)-1,2-diphenylethyl)methanesulfonamide 、 溶剂黄146 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 8.0h， 生成 (S)-6-bromo-8′-(4-methoxyphenyl)-1-methyl-2-oxo-2′-phenylspiro[indoline-3,10′-pyrano[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine]-9′-carbonitrile
  参考文献：
  名称：

  α-氰基酮与异亚丙基丙二腈的对映选择性级联反应：螺[4H-吡喃-吲哚]的不对称结构

  摘要：

  α-氰基酮首次用作迈克尔供体用于构建手性螺环化合物。在仅2摩尔％的手性多功能有机催化剂的存在下，以优异的收率和良好至优异的对映选择性制备了手性螺[4 H-吡喃-氧吲哚]衍生物。该方法为合成手性螺环恶吲哚提供了一种新方法。

  DOI：

  10.1002/ejoc.201600432
• 作为产物：
  描述：

  6-溴靛红 在 哌啶 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 oil 为溶剂， 反应 0.58h， 生成 2-(6-Bromo-1-methyl-2-oxoindol-3-ylidene)propanedinitrile
  参考文献：
  名称：

  Triphenylphosphine-Catalyzed [3+2] Cycloaddition of Allenoate and Active Olefins: Syntheses of Spirooxindole Derivatives

  摘要：

  通过三苯基膦催化的[3+2]环加成反应，成功合成了一系列螺旋化合物，反应物为活性亚甲基马隆腈和乙基2,3-丁二烯酸酯。细致的研究表明，该方法具有较高的区域选择性。产物呈现出螺氧吲哚骨架，这是一种在许多自然产物和药效活性化合物中常见的结构特征。

  DOI：

  10.1055/s-0030-1261188

文献信息

• Triphenylphosphine-Catalyzed [3+2] Cycloaddition of Allenoate and Active Olefins: Syntheses of Spirooxindole Derivatives
  作者：Xueshun Jia、Shanyan Guo、Rendong Wang、Jian Li、Chunju Li、Hongmei Deng

  DOI：10.1055/s-0030-1261188

  日期：2011.9

  A series of spiro compounds was achieved by triphenylphosphine-catalyzed [3+2] cycloaddition between active methylenemalononitrile and ethyl 2,3-butadienoate. Careful investigation showed that the present method had high regioselectivity. The products have a spirooxindole skeleton, which is a motif common in many natural products and pharmaceutically active compounds.

  通过三苯基膦催化的[3+2]环加成反应，成功合成了一系列螺旋化合物，反应物为活性亚甲基马隆腈和乙基2,3-丁二烯酸酯。细致的研究表明，该方法具有较高的区域选择性。产物呈现出螺氧吲哚骨架，这是一种在许多自然产物和药效活性化合物中常见的结构特征。
• Three-Component Condensation for the Construction of Novel Spirooxindoles
  作者：Chun Cai、Fei Ji、Mu Sun、Mei-fang Lv、Wen-bin Yi

  DOI：10.1055/s-0032-1316836

  日期：——

  using a copper azide–alkyne cycloaddition­ (CuAAC) reaction. A new route for the synthesis of novel spirooxindoles from isocyanides, dialkyl acetylenedicarboxylates, and N-substituted isatylidene derivatives through [3+2] cycloaddition has been developed. This method has several advantages, such as high regioselectivity, high yields, readily available starting materials, and one-pot operations. The

  摘要 已开发出一种新的途径，可以通过[3 + 2]环加成反应从异氰酸酯，乙炔二羧酸二烷基酯和N-取代的异亚戊二烯衍生物合成新型螺硫辛多。该方法具有几个优点，例如高区域选择性，高收率，易于获得的起始原料和一锅操作。合成的含炔烃的螺硫醇也可用于通过叠氮化铜-炔烃环加成（CuAAC）反应选择性合成含三唑的螺环化合物。 已开发出一种新的途径，可以通过[3 + 2]环加成反应从异氰酸酯，乙炔二羧酸二烷基酯和N-取代的异亚戊二烯衍生物合成新型螺硫辛多。该方法具有几个优点，例如高区域选择性，高收率，易于获得的起始原料和一锅操作。合成的含炔烃的螺硫醇也可用于通过叠氮化铜-炔烃环加成（CuAAC）反应选择性合成含三唑的螺环化合物。
• Chiral <i>C</i>₂-Symmetric Aminomethylbinaphthol as Synergistic Catalyst for Asymmetric Epoxidation of Alkylidenemalononitriles: Easy Access to Chiral Spirooxindoles
  作者：Eri Ogino、Ayu Nakamura、Satoru Kuwano、Takayoshi Arai

  DOI：10.1021/acs.orglett.0c04245

  日期：2021.3.19

  Chiral C2-symmetric 3,3′-bis((R,R)-2-naphthylethylaminomethyl)-(R)-binaphthol (AMB4) functions as an efficient organocatalyst for the asymmetric epoxidation of various alkylidenemalononitriles. The spiro-epoxyoxindole products obtained from isatilidenemalononitriles were easily transformed to the corresponding chiral dihydroquinoxalinyl spirooxindoles.

  手性C 2对称的3,3'-双（（R，R）-2-萘基乙基氨基甲基）-（R）-联萘酚（AMB4）作为有效的有机催化剂，用于各种亚烷基烯丙二腈的不对称环氧化。从异戊二烯丙二腈获得的螺-环氧氧吲哚产物容易转化为相应的手性二氢喹喔啉基螺硫醇。
• Microwave-assisted organocatalysis: phosphine-mediated Tomita Zipper cyclization affording functionalized spirooxindole
  作者：Xiao-Yan Zhang、Ze Shen、Li-Li Hu、Liang-Jun Wang、You-Shuai Lin、Jian-Wu Xie、Hai-Lei Cui

  DOI：10.1016/j.tetlet.2016.07.035

  日期：2016.8

  A microwave-assisted and phosphine-mediated Tomita Zipper cyclization of dicyanomethylideneoxindoles and ynones has been developed. Various functionalized spirooxindoles with five-membered carbocyclic ring can be obtained in moderate to good yields with moderate to excellent diastereoselectivities through in situ generation of alpha-nucleophile (up to 87% yield, >20:1 dr). (C) 2016 Elsevier Ltd. All rights reserved.
• Isocyanide-Based Multicomponent [2+2+1]-Cycloaddition Strategy to Construct Functionalized Spirocyclic Oxindoles
  作者：Jian Li、Xueshun Jia、Haohua Jie、Chunju Li

  DOI：10.1055/s-0032-1317030

  日期：——

  Isocyanide-based three-component [2+2+1]-cycloaddition reactions from isocyanides, activated alkynes, and isatylidene malononitriles were investigated to provide a new access to spirocyclic oxindole with five-membered carbon rings. The displacement of isatylidene malononitrile with oxindolylideneacetate essentially results in opposite regioselectivity, which adds to its attractiveness.