N-benzyl-3-phenylselenylpyrrol-2(5H)-one | 286470-04-0

• 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: N-benzyl-3-phenylselenylpyrrol-2(5H)-one
• 英文别名: 1-benzyl-4-phenylselanyl-2H-pyrrol-5-one
• CAS: 286470-04-0
• 化学式: C₁₇H₁₅NOSe
• 分子量: 328.272
• InChiKey: YEZHWBWMQUJJFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzyl-3-phenylselenylpyrrol-2(5H)-one 在 sodium tetrahydroborate 、 三氟甲磺酸二丁硼 、 nickel dichloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.08h， 生成 (R)-1-Benzyl-5-((R)-1-hydroxy-3-phenyl-propyl)-pyrrolidin-2-one
  参考文献：
  名称：

  Direct vinylogous aldol addition of γ-butyrolactones and γ-butyrolactams

  摘要：

  Deprotonation of N-benzyl-3-phenylselenylpyrrol-2(5H)-one 3 and furan-2(5H)-one 4 and reaction with aldehydes affords regioselectively 5-(1'-hydroxy)-gamma-butyrolactones and the aza-analogous butyrolactams with good diastereoisomeric excesses. The presence of Lewis acids enhances the diastereoisomeric ratios.This methodology is an alternative to Lewis acid mediated silyloxydiene condensation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00439-1
• 作为产物：
  描述：

  苄胺 、 2,5-dimethoxy-3-phenylselanyl-2,5-dihydrofuran 在 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 96.0h， 生成 N-benzyl-3-phenylselenylpyrrol-2(5H)-one
  参考文献：
  名称：

  Direct vinylogous aldol addition of γ-butyrolactones and γ-butyrolactams

  摘要：

  Deprotonation of N-benzyl-3-phenylselenylpyrrol-2(5H)-one 3 and furan-2(5H)-one 4 and reaction with aldehydes affords regioselectively 5-(1'-hydroxy)-gamma-butyrolactones and the aza-analogous butyrolactams with good diastereoisomeric excesses. The presence of Lewis acids enhances the diastereoisomeric ratios.This methodology is an alternative to Lewis acid mediated silyloxydiene condensation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00439-1

文献信息

• Direct vinylogous aldol addition of γ-butyrolactones and γ-butyrolactams
  作者：Marco Bella、Giovanni Piancatelli、Antonella Squarcia、Carla Trolli

  DOI：10.1016/s0040-4039(00)00439-1

  日期：2000.5

  Deprotonation of N-benzyl-3-phenylselenylpyrrol-2(5H)-one 3 and furan-2(5H)-one 4 and reaction with aldehydes affords regioselectively 5-(1'-hydroxy)-gamma-butyrolactones and the aza-analogous butyrolactams with good diastereoisomeric excesses. The presence of Lewis acids enhances the diastereoisomeric ratios.This methodology is an alternative to Lewis acid mediated silyloxydiene condensation. (C) 2000 Elsevier Science Ltd. All rights reserved.