Methyl 2-(1-benzyl-5-formyl-3-hydroxy-2-oxoindol-3-yl)prop-2-enoate | 1021359-71-6

• 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: Methyl 2-(1-benzyl-5-formyl-3-hydroxy-2-oxoindol-3-yl)prop-2-enoate
• 英文别名: methyl 2-(1-benzyl-5-formyl-3-hydroxy-2-oxoindol-3-yl)prop-2-enoate
• CAS: 1021359-71-6
• 化学式: C₂₀H₁₇NO₅
• 分子量: 351.359
• InChiKey: NTTJXFSBTBTIGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 2-(1-benzyl-5-formyl-3-hydroxy-2-oxoindol-3-yl)prop-2-enoate 、 丙烯腈 在 三乙烯二胺 作用下， 以 neat (no solvent) 为溶剂， 反应 11.0h， 以88%的产率得到2-[1-benzyl-5-(2-cyano-1-hydroxy-allyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl]-acrylic acid methylester
  参考文献：
  名称：

  An efficient and facile synthesis of divergent C-3/C-5 bis-functionalized 2-oxindoles from 5-formyl-Morita-Baylis-Hillman adducts of oxindole

  摘要：

  首次通过亲核取代反应，从3,5-双-森田-贝利斯-希尔曼(MBH)加合物的吲哚酮中高效简便地合成了C-3/C-5双官能化的2-氧代吲哚衍生物。在典型的反应条件下，第二次MBH反应观察到了更广泛的底物范围和反应加速。通过[3 + 2]环化策略合成强效的双吡唑，展示了双官能化双烯丙基衍生物的合成实用性。

  DOI：

  10.1007/s12039-015-0913-z
• 作为产物：
  描述：

  Methyl 2-(1-benzyl-3-hydroxy-5-methyl-2-oxoindol-3-yl)prop-2-enoate 在 ammonium cerium(IV) nitrate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 0.17h， 生成 Methyl 2-(1-benzyl-5-formyl-3-hydroxy-2-oxoindol-3-yl)prop-2-enoate
  参考文献：
  名称：

  A mild and efficient CAN mediated oxidation of Morita–Baylis–Hillman adducts of 5-methyl-N-alkylisatin to 5-formyl-N-alkylisatin

  摘要：

  A simple, mild and efficient CAN mediated oxidation of Morita-Baylis-Hillman adducts of 5-methyl-N-alkylisatins 1a-13a to 5-formyl-N-alkylisatins lb-13b under ambient reaction conditions is reported. Simple and isomerized 5-methyl-N-alkylisatin derivatives 1-4 have also been tested and failed to provide the corresponding formylated products. A plausible reaction mechanism has been proposed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.01.119

文献信息

• An efficient and facile synthesis of divergent C-3/C-5 bis-functionalized 2-oxindoles from 5-formyl-Morita-Baylis-Hillman adducts of oxindole
  作者：KODIRAJAN SELVAKUMAR、KANDAPALAM ARUN PRASATH LINGAM、RAMA VARMA LUXMI VARMA、POOVAN SHANMUGAVELAN

  DOI：10.1007/s12039-015-0913-z

  日期：2015.8

  An efficient and facile synthesis of divergent C-3/C-5 bis-functionalized 2-oxindole derivatives has been achieved from 3,5-bis-Morita-Baylis-Hillman (MBH) adducts of oxindole via nucleophilic substitution reaction for the first time. Wider scope of substrate and rate acceleration has been observed in second MBH reaction under typical reaction condition. The synthetic usefulness of bi-functionalized bis-allyl derivative has been demonstrated by the synthesis of potent bis-pyrazole via [3 + 2]-annulation strategy.

  首次通过亲核取代反应，从3,5-双-森田-贝利斯-希尔曼(MBH)加合物的吲哚酮中高效简便地合成了C-3/C-5双官能化的2-氧代吲哚衍生物。在典型的反应条件下，第二次MBH反应观察到了更广泛的底物范围和反应加速。通过[3 + 2]环化策略合成强效的双吡唑，展示了双官能化双烯丙基衍生物的合成实用性。
• A mild and efficient CAN mediated oxidation of Morita–Baylis–Hillman adducts of 5-methyl-N-alkylisatin to 5-formyl-N-alkylisatin
  作者：Ponnusamy Shanmugam、Vadivel Vaithiyanathan、Kodirajan Selvakumar

  DOI：10.1016/j.tetlet.2008.01.119

  日期：2008.3

  A simple, mild and efficient CAN mediated oxidation of Morita-Baylis-Hillman adducts of 5-methyl-N-alkylisatins 1a-13a to 5-formyl-N-alkylisatins lb-13b under ambient reaction conditions is reported. Simple and isomerized 5-methyl-N-alkylisatin derivatives 1-4 have also been tested and failed to provide the corresponding formylated products. A plausible reaction mechanism has been proposed. (C) 2008 Elsevier Ltd. All rights reserved.