4-(tert-butoxycarbonylamino)-3-(3-cyclopentyloxy-4-methoxyphenyl)butyric acid | 844873-54-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(tert-butoxycarbonylamino)-3-(3-cyclopentyloxy-4-methoxyphenyl)butyric acid
• 英文别名: 3-(3-Cyclopentyloxy-4-methoxyphenyl)-4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
• CAS: 844873-54-7
• 化学式: C₂₁H₃₁NO₆
• 分子量: 393.48
• InChiKey: HTDJIQNFFJKYBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(tert-butoxycarbonylamino)-3-(3-cyclopentyloxy-4-methoxyphenyl)butyric acid 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 0.67h， 以100%的产率得到4-amino-3-(3-cyclopentyloxy-4-methoxyphenyl)butyric acid hydrochloride
  参考文献：
  名称：

  Synthesis of 4-Aryl-2-pyrrolidones and β-Aryl-γ-amino-butyric Acid (GABA) Analogues by Heck Arylation of 3-Pyrrolines with Arenediazonium Tetrafluoroborates. Synthesis of (±)-Rolipram on a Multigram Scale and Chromatographic Resolution by Semipreparative Chiral Simulated Moving Bed Chromatography

  摘要：

  We report herein a new, practical, and economic synthesis of the phosphodiesterase inhibitor Rolipram on a multigram. scale as well as the synthesis of new 4-aryl pyrrolidones and beta-aryl-gamma-amino butyric acids (GABA derivatives) employing an efficient Heck-Matsuda arylation of 3-pyrroline with aryldiazonium tetrafluoroborates. Racemic Rolipram was resolved into its enantiomers using chiral simulated moving bed chromatography having the low-cost microcrystalline cellulose triacetate as a chiral stationary phase.

  DOI：

  10.1021/jo0484880
• 作为产物：
  描述：

  N-Boc-3-吡咯啉 在 palladium diacetate 、 lithium hydroxide 、 四丙基高钌酸铵 、 水 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 5.75h， 生成 4-(tert-butoxycarbonylamino)-3-(3-cyclopentyloxy-4-methoxyphenyl)butyric acid
  参考文献：
  名称：

  Synthesis of 4-Aryl-2-pyrrolidones and β-Aryl-γ-amino-butyric Acid (GABA) Analogues by Heck Arylation of 3-Pyrrolines with Arenediazonium Tetrafluoroborates. Synthesis of (±)-Rolipram on a Multigram Scale and Chromatographic Resolution by Semipreparative Chiral Simulated Moving Bed Chromatography

  摘要：

  We report herein a new, practical, and economic synthesis of the phosphodiesterase inhibitor Rolipram on a multigram. scale as well as the synthesis of new 4-aryl pyrrolidones and beta-aryl-gamma-amino butyric acids (GABA derivatives) employing an efficient Heck-Matsuda arylation of 3-pyrroline with aryldiazonium tetrafluoroborates. Racemic Rolipram was resolved into its enantiomers using chiral simulated moving bed chromatography having the low-cost microcrystalline cellulose triacetate as a chiral stationary phase.

  DOI：

  10.1021/jo0484880

文献信息

• [EN] HETEROCYCLIC 3-PHENYLPYRROLIDIN-2-ONES, THEIR PREPARATION AND USE FOR THE MANUFACTURE OF A MEDICAMENT FOR INHIBITING TUMOR NECROSIS FACTOR PRODUCTION
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：WO1993007141A1

  公开（公告）日：1993-04-15

  (EN) A compound of formula (I), wherein the substituents are as defined in the claims inhibits the production of tumor necrosis factor (TNF).(FR) Un composé de formule (I), dans laquelle les substituants ont la notation donnée dans les revendications, inhibe la production du facteur de nécrose tumorale (TNF).