Methyl 2-(3-acetyloxy-1-methyl-2-oxoindol-3-yl)prop-2-enoate | 1373120-14-9

• 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-(3-acetyloxy-1-methyl-2-oxoindol-3-yl)prop-2-enoate
• CAS: 1373120-14-9
• 化学式: C₁₅H₁₅NO₅
• 分子量: 289.288
• InChiKey: YVTXMTXUANPDOI-UHFFFAOYSA-N

物化性质

• 沸点：
  467.2±45.0 °C(predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 2-(3-acetyloxy-1-methyl-2-oxoindol-3-yl)prop-2-enoate 在 氢溴酸 作用下， 以 二氯甲烷 为溶剂， 生成 Methyl 3-bromo-2-(1-methyl-2-oxoindol-3-ylidene)propanoate
  参考文献：
  名称：

  Unprecedented One-Pot, Domino Tertiary Alcohol Protection–Michael Type Addition of Halides to Morita–Baylis–Hillman Adduct of Isatin with RCOX/K₂CO₃: Diastereoselective Synthesis of Oxindole Appended β-Halo Esters

  摘要：

  A facile method utilizing RDOX/K2CO3 as a novel reagent for conjugate addition of hydrogen halide, in addition to tertiary (3 degrees)-hydroxyl protection that leads to the synthesis of functionalized beta-halo Morita-Baylis-Hillman ester appended oxindoles, has been developed. The diastereoselective one-pot O-acylation-hydrohalogenation observed cannot otherwise be performed by treatment with hydrohalide. Deprotection of a 3 degrees-hydroxyl protecting group has also been demonstrated by treatment with hydrochloric acid.

  DOI：

  10.1021/ol303554c
• 作为产物：
  描述：

  1-甲基靛红 在 三乙烯二胺 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 75.0h， 生成 Methyl 2-(3-acetyloxy-1-methyl-2-oxoindol-3-yl)prop-2-enoate
  参考文献：
  名称：

  Unprecedented One-Pot, Domino Tertiary Alcohol Protection–Michael Type Addition of Halides to Morita–Baylis–Hillman Adduct of Isatin with RCOX/K₂CO₃: Diastereoselective Synthesis of Oxindole Appended β-Halo Esters

  摘要：

  A facile method utilizing RDOX/K2CO3 as a novel reagent for conjugate addition of hydrogen halide, in addition to tertiary (3 degrees)-hydroxyl protection that leads to the synthesis of functionalized beta-halo Morita-Baylis-Hillman ester appended oxindoles, has been developed. The diastereoselective one-pot O-acylation-hydrohalogenation observed cannot otherwise be performed by treatment with hydrohalide. Deprotection of a 3 degrees-hydroxyl protecting group has also been demonstrated by treatment with hydrochloric acid.

  DOI：

  10.1021/ol303554c

文献信息

• Catalyst-free synthesis of 3-alkenyloxindoles from isatin-derived Morita–Baylis–Hillman carbonates
  作者：Lin Jiang、Yong-Gen Li、Hang Li、Ming-Wei Yuan、Yong-Ming Chuan、Hong-Li Li、Ming-Long Yuan

  DOI：10.3184/174751917x14878812592652

  日期：2017.3

  A variety of biologically and synthetically useful 3-alkenyloxindoles were rapidly synthesised via an S_N2′-type allylic substitution reaction of isatin-derived Morita–Baylis–Hillman carbonates with sodium sulfinates. The syntheses were conducted under catalyst-free reaction conditions and good to excellent product yields (up to 96%) and Z/E selectivities (up to >20:1) were obtained.

  通过靛红衍生的 Morita-Baylis-Hillman 碳酸酯与硫酸钠的 SN2′型烯丙基取代反应，快速合成了多种生物和合成上有用的 3-烯基吲哚。合成是在无催化剂的反应条件下进行的，获得了良好至卓越的产品收率（高达 96%）和 Z/E 选择性（高达 20:1）。
• Development of a mild and efficient protocol for the protection and O-alkylation of allyl alcohols
  作者：Kodirajan Selvakumar、Kandapalam Arun Prasath Lingam、Rama Varma Luxmi Varma

  DOI：10.1039/c4ra06841f

  日期：——

  An efficient, pyridine-free protocol has been developed for the protection of 3°-allyl alcohol of oxindole using a mild base of potassium carbonate under microwave irradiation conditions. The methodology has been tested with a variety of substrates and protecting group reagents, which provides a clean and good yield of desired products within a short reaction time.

  已开发出一种高效、无吡啶的方案，用于在微波辐射条件下使用碳酸钾作为温和碱对氧吲哚的3°-烯丙醇进行保护。该方法已经通过多种底物和保护基试剂进行测试，能够在短时间内提供所需产物的干净且高收率的产物。
• Diastereo- and Enantioselective [3 + 2] Cycloaddition Reaction of Morita–Baylis–Hillman Carbonates of Isatins with <i>N</i>-Phenylmaleimide Catalyzed by Me-DuPhos
  作者：Yan Wang、Li Liu、Tao Zhang、Neng-Jun Zhong、Dong Wang、Yong-Jun Chen

  DOI：10.1021/jo3002535

  日期：2012.4.20

  A Me-DuPhos-catalyzed efficient asymmetric [3 + 2] cycloaddition reaction between Morita-Baylis-Hillman carbonates of isatins and N-phenylmaleimide has been developed. This reaction constructs three chiral centers in one step to afford spirocyclopentaneoxindoles in good yields (up to 84%) with excellent diastereo- and enantioselectivies (up to 99% ee).