(R)-苄基(1,2,3,4-四氢喹啉-3-基)氨基甲酸甲酯 | 166742-98-9

• 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
• 中文名称: (R)-苄基(1,2,3,4-四氢喹啉-3-基)氨基甲酸甲酯
• 中文别名: (R)-苄基甲基(1,2,3,4-四氢喹啉-3-基)氨基甲酸酯
• 英文名称: (R)-methyl-(1,2,3,4-tetrahydro-3-quinolinyl)carbamic acid, phenylmethyl ester
• 英文别名: (R)-Benzyl methyl(1,2,3,4-tetrahydroquinolin-3-yl)carbamate；benzyl N-methyl-N-[(3R)-1,2,3,4-tetrahydroquinolin-3-yl]carbamate
• CAS: 166742-98-9
• 化学式: C₁₈H₂₀N₂O₂
• 分子量: 296.369
• InChiKey: CNRFRMQVMVEMAF-MRXNPFEDSA-N

物化性质

• 沸点：
  466.7±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  (R)-苄基(1,2,3,4-四氢喹啉-3-基)氨基甲酸甲酯 在 palladium dihydroxide 氢气 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 、 三乙胺 、 甲苯 为溶剂， -5.0~25.0 ℃ 、344.73 kPa 条件下， 反应 97.0h， 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)-n-甲基-1,2,3,4-四氢喹啉-3-胺 生成 (R)-苄基(1,2,3,4-四氢喹啉-3-基)氨基甲酸甲酯
  参考文献：
  名称：

  J. Org. Chem. 1997, 62, 6582-6587

  摘要：

  DOI：

文献信息

• Heterocyclic amines having central nervous system activity
  申请人：Pharmacia & Upjohn Company

  公开号：US05652245A1

  公开（公告）日：1997-07-29

  Tricyclic nitrogen containing compounds, having anxiolytic and anti-depressant activity and central nervous system activity of the following structural formula: ##STR1## and pharmaceutically acceptable salts thereof wherein R.sub.1 and R.sub.2 are independently hydrogen, C.sub.1-6 alkyl or R.sub.1 and R.sub.2 are joined to form pyrrolidine, piperidine, morpholine or imidazole. X is OCH.sub.3, SO.sub.2 R.sub.3, SO.sub.2 CF.sub.3 or CN where R.sub.3 is C.sub.1-6 alkyl or an Aryl; and Y is hydrogen, Cl, Br, F, CN, CONR.sub.1 R.sub.2, CF.sub.3, OCH.sub.3, SO.sub.2 NR.sub.1 R.sub.2. These new compounds are suitable for treating anxiolytic disorder, schizophrenia, Parkinson's disease, anxiety, depression or as compounds for lowering blood pressure or treating migraine headaches in patients in need of such treatment.

  含有抗焦虑和抗抑郁活性以及以下结构式的中枢神经系统活性的三环氮含有化合物：##STR1##及其药学上可接受的盐，其中R.sub.1和R.sub.2独立地是氢、C.sub.1-6烷基或R.sub.1和R.sub.2连接形成吡咯烷、哌啶、吗啉或咪唑。X为OCH.sub.3、SO.sub.2 R.sub.3、SO.sub.2 CF.sub.3或CN，其中R.sub.3为C.sub.1-6烷基或芳基；Y为氢、Cl、Br、F、CN、CONR.sub.1 R.sub.2、CF.sub.3、OCH.sub.3、SO.sub.2 NR.sub.1 R.sub.2。这些新化合物适用于治疗焦虑障碍、精神分裂症、帕金森病、焦虑、抑郁或作为降低血压或治疗偏头痛的化合物，适用于需要此类治疗的患者。
• (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。
• USRE40278E1
  申请人：——

  公开号：USRE40278E1

  公开（公告）日：2008-04-29