1-[1-(4-methoxyphenyl)ethyl]-3-methyl-1,5-dihydropyrrol-2-one | 864158-86-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-[1-(4-methoxyphenyl)ethyl]-3-methyl-1,5-dihydropyrrol-2-one
• 英文别名: 1-[(1S)-1-(4-methoxyphenyl)ethyl]-4-methyl-2H-pyrrol-5-one
• CAS: 864158-86-1
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: YTWBYZJFHVCYCN-NSHDSACASA-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：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  1-[1-(4-methoxyphenyl)ethyl]-3-methyl-1,5-dihydropyrrol-2-one 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 xylene 为溶剂， 反应 51.5h， 生成 5-allyl-1-[1-(4-methoxyphenyl)ethyl]-3-methyl-1,5-dihydropyrrol-2-one
  参考文献：
  名称：

  Diastereoselective protonation of extended pyrrol-3-en-2-one enolates: an attempted ‘de-epimerisation’

  摘要：

  The extended cyclic enolate derived from a simple pyrrol-3-en-2-one (butenolactam) was deuterated at the 5-position with very high diastereoselectivity if the nitrogen atom carries an alpha-methyl-p-methoxybenzyl group. A similar diastereoselective protonation was observed in a pyrrol-3-en-2-one formed by dearomatising cyclisation of a pyrrole. Protonation of an N-alpha-methyl-p-methoxybenzyl dihydroisoindolone lacked stereoselectivity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.05.042
• 作为产物：
  描述：

  (S)-(-)-1-(4-甲氧基苯)乙胺 在 4-二甲氨基吡啶 、 Grubbs catalyst first generation 、 正丁基锂 、 sodium hydride 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 1-[1-(4-methoxyphenyl)ethyl]-3-methyl-1,5-dihydropyrrol-2-one
  参考文献：
  名称：

  Diastereoselective protonation of extended pyrrol-3-en-2-one enolates: an attempted ‘de-epimerisation’

  摘要：

  The extended cyclic enolate derived from a simple pyrrol-3-en-2-one (butenolactam) was deuterated at the 5-position with very high diastereoselectivity if the nitrogen atom carries an alpha-methyl-p-methoxybenzyl group. A similar diastereoselective protonation was observed in a pyrrol-3-en-2-one formed by dearomatising cyclisation of a pyrrole. Protonation of an N-alpha-methyl-p-methoxybenzyl dihydroisoindolone lacked stereoselectivity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.05.042

文献信息

• Diastereoselective protonation of extended pyrrol-3-en-2-one enolates: an attempted ‘de-epimerisation’
  作者：Jonathan Clayden、Rachel Turnbull、Ivan Pinto

  DOI：10.1016/j.tetasy.2005.05.042

  日期：2005.7

  The extended cyclic enolate derived from a simple pyrrol-3-en-2-one (butenolactam) was deuterated at the 5-position with very high diastereoselectivity if the nitrogen atom carries an alpha-methyl-p-methoxybenzyl group. A similar diastereoselective protonation was observed in a pyrrol-3-en-2-one formed by dearomatising cyclisation of a pyrrole. Protonation of an N-alpha-methyl-p-methoxybenzyl dihydroisoindolone lacked stereoselectivity. (c) 2005 Elsevier Ltd. All rights reserved.