5-ethoxy-1-[(1R)-1-phenylethyl]pyrrolidin-2-one | 373640-31-4

• 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: 5-ethoxy-1-[(1R)-1-phenylethyl]pyrrolidin-2-one
• CAS: 373640-31-4
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: JRULEKKTEZJHDD-YNODCEANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-ethoxy-1-[(1R)-1-phenylethyl]pyrrolidin-2-one 在 三乙基硼 、 三正丁基氢锡 、 四氯化钛 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 2-[5-Oxo-1-((R)-1-phenyl-ethyl)-pyrrolidin-2-yl]-propionic acid methyl ester
  参考文献：
  名称：

  Influence of N-substituted lactams on acyclic free radical based hydrogen transfer

  摘要：

  anti Relative stereochemistry is achieved in the hydrogen-transfer reaction of a lactam adjacent to the carbon-centered radical. The sense of diastereoselectivity is reversed using N-substituted lactams, and optimal results favoring syn reduced products are obtained with an alpha -methylbenzyl group and a Boc group. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01213-8
• 作为产物：
  描述：

  γ-丁内酯 、 乙醇 、 R(+)-alpha-甲基苄胺 生成 5-ethoxy-1-[(1R)-1-phenylethyl]pyrrolidin-2-one
  参考文献：
  名称：

  Influence of N-substituted lactams on acyclic free radical based hydrogen transfer

  摘要：

  anti Relative stereochemistry is achieved in the hydrogen-transfer reaction of a lactam adjacent to the carbon-centered radical. The sense of diastereoselectivity is reversed using N-substituted lactams, and optimal results favoring syn reduced products are obtained with an alpha -methylbenzyl group and a Boc group. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01213-8

文献信息

• <i>N</i>-Trialkylsilyl Bistrifluoromethanesulfonimides (R₃SiNTf₂) Are Powerful Catalysts for the Highly Efficient α-Amido Alkylation Reactions of Silicon-Based Nucleophiles
  作者：Raja Ben Othman、Till Bousquet、Mohamed Othman、Vincent Dalla

  DOI：10.1021/ol052357j

  日期：2005.11.1

  In situ formed N-trialkylsilyl bistrifluoromethanesulforlimides (R3SiNTf2) species have been shown to efficiently catalyze the nucleophilic substitution reactions of chiral 5-oxypyrrolidin-2-ones by silicon-based nucleophiles. The reaction rates were significantly accelerated in comparison to the cases where the usual triflate catalysts are used. Adducts were obtained in high yields and usual stereoselectivities within short reaction times, and the process was compatible with a semipreparative scale.
• Toward Improving the Chemistry of <i>N</i>-Acyliminium Ions:  Nucleophilic Substitution Reactions of Pyrrolidinone Derivatives with Trialkylsilyl Nucleophiles Catalyzed by Triisopropylsilyltrifluoromethane Sulfonate (TIPSOTf)
  作者：Raja Ben Othman、Till Bousquet、Anthony Fousse、Mohamed Othman、Vincent Dalla

  DOI：10.1021/ol050576z

  日期：2005.7.1

  Nucleophilic substitution reactions of racemic and chiral 5-acetoxy-, 5-ethoxy-, and 5-methoxypyrrolidin-2-ones by silicon-based nucleophiles were efficiently catalyzed by TIPSOTf. This process was found to be general and accommodates a broad range of substrate-nucleophile combinations.