benzyl 3,3-dibenzoyl-2-ethoxypyrrolidine-1-carboxylate | 1428771-83-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 3,3-dibenzoyl-2-ethoxypyrrolidine-1-carboxylate
• CAS: 1428771-83-8
• 化学式: C₂₈H₂₇NO₅
• 分子量: 457.526
• InChiKey: FKAQCKBRODWIKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  N-Cbz-2-溴乙胺 、 2-(ethoxymethylene)-1,3-diphenylpropane-1,3-dione 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 以57%的产率得到benzyl 3,3-dibenzoyl-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