4-ethyl-1-(4-methoxybenzyl)-4-methylpyrrolidine-2,5-dione | 166324-36-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-ethyl-1-(4-methoxybenzyl)-4-methylpyrrolidine-2,5-dione
• 英文别名: 3-Ethyl-1-[(4-methoxyphenyl)methyl]-3-methylpyrrolidine-2,5-dione
• CAS: 166324-36-3
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: BNWUYOGVAUABFU-UHFFFAOYSA-N

物化性质

• 沸点：
  434.7±28.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-ethyl-1-(4-methoxybenzyl)-4-methylpyrrolidine-2,5-dione 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以47%的产率得到乙琥胺
  参考文献：
  名称：

  Uncatalyzed cationic olefin cyclizations of N-vinylic α-chloro-α-thioacetamides. Formation of β- and γ-lactams

  摘要：

  N-Vinylic alpha-chloro-alpha-thioacetamides were found to cyclize without a catalyst in two different manners depending upon the nature of the substituents at the terminus of the N-vinylic bond. Thus, bis(phenylthio)-substituted enamides 8a-c cyclized in a 4-exo-trig manner to give 4-methylene-beta-lactams 10a-c, whereas mono(phenylthio)-, monophenyl-, diphenyl-, and dialkyl-substituted congeners 23a,b, 28, and 38 cyclized in a 5-endo-trig manner to give gamma-lactams 26a,b, 30, and 39, respectively. The product 38 was transformed into an anticonvulsant agent ethosuximide (42).

  DOI：

  10.1016/0040-4020(95)00056-e
• 作为产物：
  描述：

  4-ethyl-5-hydroxy-1-(4-methoxybenzyl)-4-methylpyrrolidin-2-one 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以56%的产率得到4-ethyl-1-(4-methoxybenzyl)-4-methylpyrrolidine-2,5-dione
  参考文献：
  名称：

  Uncatalyzed cationic olefin cyclizations of N-vinylic α-chloro-α-thioacetamides. Formation of β- and γ-lactams

  摘要：

  N-Vinylic alpha-chloro-alpha-thioacetamides were found to cyclize without a catalyst in two different manners depending upon the nature of the substituents at the terminus of the N-vinylic bond. Thus, bis(phenylthio)-substituted enamides 8a-c cyclized in a 4-exo-trig manner to give 4-methylene-beta-lactams 10a-c, whereas mono(phenylthio)-, monophenyl-, diphenyl-, and dialkyl-substituted congeners 23a,b, 28, and 38 cyclized in a 5-endo-trig manner to give gamma-lactams 26a,b, 30, and 39, respectively. The product 38 was transformed into an anticonvulsant agent ethosuximide (42).

  DOI：

  10.1016/0040-4020(95)00056-e

文献信息

• Tetrahedron 1995, 51, 2929-2938
  作者：

  DOI：——

  日期：——
• Uncatalyzed cationic olefin cyclizations of N-vinylic α-chloro-α-thioacetamides. Formation of β- and γ-lactams
  作者：Hiroyuki Ishibashi、Tohru Nakaharu、Masako Nishimura、Atsuko Nishikawa、Chisato Kameoka、Masazumi Ikeda

  DOI：10.1016/0040-4020(95)00056-e

  日期：1995.3

  N-Vinylic alpha-chloro-alpha-thioacetamides were found to cyclize without a catalyst in two different manners depending upon the nature of the substituents at the terminus of the N-vinylic bond. Thus, bis(phenylthio)-substituted enamides 8a-c cyclized in a 4-exo-trig manner to give 4-methylene-beta-lactams 10a-c, whereas mono(phenylthio)-, monophenyl-, diphenyl-, and dialkyl-substituted congeners 23a,b, 28, and 38 cyclized in a 5-endo-trig manner to give gamma-lactams 26a,b, 30, and 39, respectively. The product 38 was transformed into an anticonvulsant agent ethosuximide (42).