乙基(2Z)-(1-苄基-2-氧代-1,2-二氢-3H-吲哚-3-亚基)(氰基)乙酸酯 | 26960-51-0

• 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
• 中文名称: 乙基(2Z)-(1-苄基-2-氧代-1,2-二氢-3H-吲哚-3-亚基)(氰基)乙酸酯
• 英文名称: ethyl-2-(1-benzyl-2-oxoindolin-3-ylidene)-2-cyanoacetate
• 英文别名: ethyl (1-benzyl-2-oxo-2,3-dihydro-1H-indol-3-ylidene)cyanoacetate；Ethyl 2-(1-benzyl-2-oxoindol-3-ylidene)-2-cyanoacetate
• CAS: 26960-51-0
• 化学式: C₂₀H₁₆N₂O₃
• mdl: MFCD00187665
• 分子量: 332.359
• InChiKey: ILSBZJQRTQRMSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  70.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  1-ethyl-1H-2,1-benzothiazin-4(3H)-one 2,2-dioxide 、 乙基(2Z)-(1-苄基-2-氧代-1,2-二氢-3H-吲哚-3-亚基)(氰基)乙酸酯 在 三乙醇胺 作用下， 以 乙醇 为溶剂， 以41%的产率得到spiro[(2-amino-3-ethoxycarbonyl-6-ethyl-4,6-dihydropyrano[3,2-c][2,1]benzothiazine-5,5-dioxide)-4,3'-(1'-benzyl-indolin-2'-one)]
  参考文献：
  名称：

  An efficient, three-component synthesis and molecular structure of derivatives of 2-amino-3-R-6-ethyl-4,6-dihydropyrano[3,2-c][2,1]benzothiazine-5,5-dioxide spirocombined with a 2-oxindole nucleus

  摘要：

  Spiro[(2-amino-3-R-6-ethyl-4,6-dihydropyrano[3,2-c][2,1]benzothiazine-5,5-dioxide)-4,3'-(1'-R'-5'-R ''-indolin-2'-one)] compounds were synthesized based on the three-component interaction of benzo[c][2,1]thiazin-4-on 2,2-dioxide with corresponding isatins and appropriate methylene active nitriles in the presence of a base as a catalyst. The molecular structures of the target compounds were proved uniquely by the X-ray diffraction analysis method. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.09.005
• 作为产物：
  描述：

  1-苄基-1H-吲哚-2,3-二酮 、 氰乙酸乙酯 在 三乙醇胺 作用下， 以 乙醇 为溶剂， 以72%的产率得到乙基(2Z)-(1-苄基-2-氧代-1,2-二氢-3H-吲哚-3-亚基)(氰基)乙酸酯
  参考文献：
  名称：

  Synthesis of fused 2′-amino-3′-R-spiro-[indole-3,4′-pyran]-2(1H)-ones

  摘要：

  An efficient one-pot procedure has been proposed for the synthesis of fused 2'-amino-3'-R-spiro-[indole-3,4'-pyran]-2(1H)-ones via base-catalyzed three-component condensation of isatins with the corresponding nitriles and 1,3-diketones.

  DOI：

  10.1134/s1070428008120117

文献信息

• Synthesis of new heterocyclic systems—substituted spiro[chromene-4,3′-indoles] and spiro[indole-3,4′-quinolines]
  作者：S. A. Pogosyan、Dzh. A. Avakimyan、H. M. Stepanyan

  DOI：10.1134/s1070428016090098

  日期：2016.9

  Methods have been developed for the synthesis of new heterocyclic systems, spiro[chromene-4,3′- indoles] and spiro[indole-3,4′-quinolines] by the base-catalyzed domino reaction of isatins with 5,5-dimethylcyclohexane- 1,3-dione (or 5,5-dimethyl-3-anilinocyclohex-2-en-1-one) and ethyl cyanoacetate.

  已经开发了通过靛红与5,5-二甲基环己烷的碱催化多米诺反应合成新的杂环系统，螺环[chromene-4,3'-吲哚]和螺环[吲哚-3,4'-喹啉]的方法。 -1，3-二酮（或5，5-二甲基-3-苯胺基环己二-2-烯-1-酮）和氰基乙酸乙酯。
• Engaging thieno[2,3‐b]indole‐2,3‐dione for the efficient synthesis of spiro[indoline‐3,4′‐thiopyrano[2,3‐b]indole] by reaction with <i>N</i> ‐substituted isatilidenes
  作者：Noble V. Thomas、Vidya Sathi、Ani Deepthi、Sruthi Leena、Sidharth Chopra

  DOI：10.1002/jhet.4147

  日期：2021.1

  A simple and efficient method, proceeding through a new mechanistic pathway, for the synthesis of spiro[indoline‐3,4‐thiopyrano[2.3‐b]indole derivatives have been developed by exploiting the reaction of thieno[2,3‐b]indole‐2,3‐dione with N‐substituted isatilidenes. The compounds synthesized have been screened for antibacterial activity. The generality of the reaction and mechanistic rationale are presented

  通过利用噻吩并[2,3-b]吲哚的反应，开发了一种简单有效的方法，通过新的机理途径合成螺[吲哚啉-3,4-硫代吡喃并[2.3-b]吲哚衍生物-2,3-二酮与N-取代的异戊二烯。已经筛选了合成的化合物的抗菌活性。介绍了反应的一般性和机理原理。
• 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。
• Palladium-Catalyzed Bis-Functionalization of Isatylidenes: A Facile Route towards Spiro-Indol-2-ones
  作者：Sholly Clair George、Jubi John、Saithalavi Anas、Joshni John、Yoshinori Yamamoto、Eringathodi Suresh、K. V. Radhakrishnan

  DOI：10.1002/ejoc.201000604

  日期：——

  construction of 3,3-disubstituted indol-2-ones from isatylidenes by utilizing amphiphilic bis-π-allylpalladium and related intermediates. The developed strategy is a new method for the quaternization of position 3 of the indol-2-one towards disubstituted functionalized indol-2-ones. These products were subjected to ring-closing metathesis towards the synthesis of spiro[cyclohexene-1,3′-indol]-2′-ones

  通过利用两亲性双-π-烯丙基钯和相关中间体，开发了一种有效的协议，用于从 isatylidenes 构建 3,3-二取代 indol-2-ones。所开发的策略是一种将 indol-2-one 的 3 位季铵化为双取代的功能化 indol-2-one 的新方法。这些产物经过闭环复分解反应合成螺[环己烯-1,3'-吲哚]-2'-酮和螺[oxep​​-5-ene-2,3'-吲哚]-2'-酮，具有生物学意义。
• Construction of highly enantioselective spiro-oxindole derivatives with fused chromene via organocascade catalysis
  作者：Prathibha Kumari、Sekhar Nandi、Gaurav Kumar、Noorul H. Khan、Rukhsana I. Kureshy、Sayed H. R. Abdi、E. Suresh、Hari C. Bajaj

  DOI：10.1039/c6ra06812j

  日期：——

  A first highly enantioselective addition of naphthols and sesamol to indolylidene cyanoacetate derived from isatins was carried out in presence of bi-functional quinine thiourea as organocatalyst. Under optimized reaction condition...

  在存在双官能团奎宁硫脲作为有机催化剂的情况下，将萘酚和芝麻酚首先高度对映选择性地加到衍生自靛红的吲哚亚基氰乙酸酯中。在优化的反应条件下...