Benzyl 3-(benzenesulfonyl)-3-cyano-2-ethoxypyrrolidine-1-carboxylate | 1428771-84-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzyl 3-(benzenesulfonyl)-3-cyano-2-ethoxypyrrolidine-1-carboxylate
• 英文别名: benzyl 3-(benzenesulfonyl)-3-cyano-2-ethoxypyrrolidine-1-carboxylate
• CAS: 1428771-84-9
• 化学式: C₂₁H₂₂N₂O₅S
• 分子量: 414.482
• InChiKey: VQQIDHYCKIRQST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-Cbz-2-溴乙胺 、 3-ethoxy-2-(phenylsulfonyl)acrylonitrile 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 以98%的产率得到Benzyl 3-(benzenesulfonyl)-3-cyano-2-ethoxypyrrolidine-1-carboxylate
  参考文献：
  名称：

  Tandem aza-Michael/spiro-ring closure sequence: access to a versatile scaffold and total synthesis of (±)-coerulescine

  摘要：

  The total synthesis of the alkaloid (+/-)-coerulescine is presented. The key step of this approach is an efficient tandem aza-Michael initiated ring closure (aza-MIRC) process between ethoxymethylene-oxindole and benzyl(2-bromoethyl)carbamate. The potency of the aza-MIRC reaction was first tested onto less challenging Michael acceptors and led in good yields to the corresponding N-Cbz alpha-alkoxy-beta-gem-disubstituted pyrrolidines. The resulting N-acyliminium precursor obtained from ethoxymethylidene-oxindole was efficiently converted in four steps, including 2 deprotections, into the targeted (+/-)-coerulescine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.047

文献信息

• Tandem aza-Michael/spiro-ring closure sequence: access to a versatile scaffold and total synthesis of (±)-coerulescine
  作者：Meral Görmen、Ronan Le Goff、Ata Martin Lawson、Adam Daïch、Sébastien Comesse

  DOI：10.1016/j.tetlet.2013.02.047

  日期：2013.4

  The total synthesis of the alkaloid (+/-)-coerulescine is presented. The key step of this approach is an efficient tandem aza-Michael initiated ring closure (aza-MIRC) process between ethoxymethylene-oxindole and benzyl(2-bromoethyl)carbamate. The potency of the aza-MIRC reaction was first tested onto less challenging Michael acceptors and led in good yields to the corresponding N-Cbz alpha-alkoxy-beta-gem-disubstituted pyrrolidines. The resulting N-acyliminium precursor obtained from ethoxymethylidene-oxindole was efficiently converted in four steps, including 2 deprotections, into the targeted (+/-)-coerulescine. (C) 2013 Elsevier Ltd. All rights reserved.