(R)-benzyl 1-(methoxycarbamoyl)-1,2,3,4-tetrahydroquinolin-3-yl(methyl)carbamate | 166742-99-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (R)-benzyl 1-(methoxycarbamoyl)-1,2,3,4-tetrahydroquinolin-3-yl(methyl)carbamate
• 英文别名: benzyl N-[(3R)-1-(methoxycarbamoyl)-3,4-dihydro-2H-quinolin-3-yl]-N-methylcarbamate
• CAS: 166742-99-0
• 化学式: C₂₀H₂₃N₃O₄
• 分子量: 369.42
• InChiKey: VSTVPNVVKXAOLZ-QGZVFWFLSA-N

物化性质

• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  71.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-benzyl 1-(methoxycarbamoyl)-1,2,3,4-tetrahydroquinolin-3-yl(methyl)carbamate 在 palladium dihydroxide 氢气 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 乙醇 、 氯仿 为溶剂， -5.0~25.0 ℃ 、344.73 kPa 条件下， 反应 25.0h， 生成 (R)-5-(甲基氨基)-5,6-二氢-1H-咪唑并[4,5,1-ij]喹啉-2(4h)-酮
  参考文献：
  名称：

  Synthesis of the Selective D₂ Receptor Agonist PNU-95666E from d-Phenylalanine Using a Sequential Oxidative Cyclization Strategy

  摘要：

  Compound 1 (PNU-95666E) is a selective and high-affinity agonist at the dopamine D-2 receptor subtype and is of interest as a potential agent for the treatment of Parkinson's disease. Requiring a synthetic route amenable to scale-up, a synthesis of this enantiomerically pure tricyclic compound was developed, starting from D-phenylalanine. Critical to the success of this synthesis were two oxidative nitrogen annulations to provide the tricyclic ring system. A highly efficient reduction with borane-methyl sulfide was used to reduce three different functional groups, a total of six hydrides transferred, with no concomitant racemization, contributing to the synthesis of 1 in eight steps with an overall yield of 26%. The utility of this synthetic route has been demonstrated by the completion this synthesis on multikilogram scale.

  DOI：

  10.1021/jo970526a
• 作为产物：
  描述：

  (R)-苄基(1,2,3,4-四氢喹啉-3-基)氨基甲酸甲酯 以 四氢呋喃 、 三乙胺 、 甲苯 为溶剂， 反应 72.0h， 生成 (R)-benzyl 1-(methoxycarbamoyl)-1,2,3,4-tetrahydroquinolin-3-yl(methyl)carbamate
  参考文献：
  名称：

  Synthesis of the Selective D₂ Receptor Agonist PNU-95666E from d-Phenylalanine Using a Sequential Oxidative Cyclization Strategy

  摘要：

  Compound 1 (PNU-95666E) is a selective and high-affinity agonist at the dopamine D-2 receptor subtype and is of interest as a potential agent for the treatment of Parkinson's disease. Requiring a synthetic route amenable to scale-up, a synthesis of this enantiomerically pure tricyclic compound was developed, starting from D-phenylalanine. Critical to the success of this synthesis were two oxidative nitrogen annulations to provide the tricyclic ring system. A highly efficient reduction with borane-methyl sulfide was used to reduce three different functional groups, a total of six hydrides transferred, with no concomitant racemization, contributing to the synthesis of 1 in eight steps with an overall yield of 26%. The utility of this synthetic route has been demonstrated by the completion this synthesis on multikilogram scale.

  DOI：

  10.1021/jo970526a

文献信息

• (R)-5,6-dihydro-5-(methylamino)-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one maleate
  申请人：——

  公开号：US20010053386A1

  公开（公告）日：2001-12-20

  The sustained release tablet of (R)-5,6-dihydro-5-(methylamino)-4H-imidazo[4,5-ij]-quinolin-2(1H)-one (Z)-2-butenedioate (1:1) which is disclosed permits twice daily administration of (R)-5,6-dihydro-5-(methylamino)-4H-imidazo[4,5-ij]-quinolin-2(1H)-one (Z)-2-butenedioate (1:1) to treat humans with Parkinson's disease.

  (R)-5,6-二氢-5-(甲基氨基)-4H-咪唑并[4,5-ij]喹啉-2(1H)-酮(Z)-2-丁烯二酸(1:1)的持续释放片，允许每天两次口服(R)-5,6-二氢-5-(甲基氨基)-4H-咪唑并[4,5-ij]喹啉-2(1H)-酮(Z)-2-丁烯二酸(1:1)，用于治疗帕金森病人。
• Sustained release tablet formulation to treat Parkinson's disease
  申请人：Pharmacia & Upjohn Company

  公开号：US06197339B1

  公开（公告）日：2001-03-06

  The sustained release tablet of (R)-5,6-dihydro-5-(methylamino)-4H-imidazo[4,5-ij]-quinolin-2(1H)-one (Z)-2-butenedioate (1:1) which is disclosed permits twice daily administration of (R)-5,6-dihydro-5-(methylamino)-4H-imidazo[4,5-ij]-quinolin-2(1H)-one (Z)-2-butenedioate (1:1) to treat humans with Parkinson's disease.

  (R)-5,6-二氢-5-(甲基氨基)-4H-咪唑并[4,5-ij]喹啉-2(1H)-酮(Z)-2-丁烯二酸(1:1)的缓释片剂可实现每日两次给予(R)-5,6-二氢-5-(甲基氨基)-4H-咪唑并[4,5-ij]喹啉-2(1H)-酮(Z)-2-丁烯二酸(1:1)治疗帕金森病患者。