9-Chloro-10b-methyl-5,6-dihydro-[1,3]oxazolo[2,3-a]isoquinoline-2,3-dione | 165611-14-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 9-Chloro-10b-methyl-5,6-dihydro-[1,3]oxazolo[2,3-a]isoquinoline-2,3-dione
• CAS: 165611-14-3
• 化学式: C₁₂H₁₀ClNO₃
• 分子量: 251.669
• InChiKey: IBMANDUCNIUZMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  9-Chloro-10b-methyl-5,6-dihydro-[1,3]oxazolo[2,3-a]isoquinoline-2,3-dione 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 7-chloro-1-methyl-3,4-dihydroisoquinoline
  参考文献：
  名称：

  新型非苯二氮卓类睡眠诱导剂三环吡啶酮衍生物Ro 41-3696的权宜之计

  摘要：

  （S）-10-氯-1-（3-乙氧基吡咯烷-1-基）-3-苯基-6,7-二氢-4H-苯并[a]-喹啉--4-酮的简短技术合成（1）由2-（4-氯苯基）乙胺（2）描述。

  DOI：

  10.1016/0040-4039(95)00387-r
• 作为产物：
  描述：

  4-氯苯乙胺 在 sodium hydroxide 、 三氯化铁 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 9-Chloro-10b-methyl-5,6-dihydro-[1,3]oxazolo[2,3-a]isoquinoline-2,3-dione
  参考文献：
  名称：

  A modified Bischler-Napieralski procedure for the synthesis of 3-aryl-3,4-dihydroisoquinolines

  摘要：

  A modification of the Bischler-Napieralski reaction for the cyclization of (1,2-diphenylethyl)amides to the 3-aryl-3,4-dihydroisoquinolines is presented. Elimination of the amide group as the nitrile via the retro-Ritter reaction is avoided by its conversion to an N-acyliminium intermediate with oxalyl chloride-FeCl3. Removal of the oxalyl group in refluxing MeOH-sulfuric acid provides the 3,4-dihydroisoquinolines in moderate to high yields. The method is also highly effective with (2-phenylethyl)amides.

  DOI：

  10.1021/jo00021a014

文献信息

• Process for the preparation of a benzo(a)quinolizione derivative
  申请人：Hoffmann-La Roche Inc.

  公开号：US05578728A1

  公开（公告）日：1996-11-26

  The invention is concerned with a process for the preparation of a benzo[a]quinolizinone derivative of the formula ##STR1## by reacting a compound of the formula ##STR2## wherein X is halogen and Ph is phenyl, with carbon monoxide in the presence of a carbonylation catalyst and in the presence of (S)-3-ethoxypyrrolidine or a lower alkanol or water; where a lower alkyl ester of the 10-chloro-6,7-dihydro-4-oxo-3 -phenyl-4H-benzo[a]quinolizine-1-carboxylic acid has been obtained, converting this into the corresponding free acid; and, where the 10-chloro-6,7-dihydro-4-oxo-3-phenyl-4H-benzo[a]quinolizine-1-carboxylic acid has been obtained, reacting a reactive derivative thereof with (S)-3-ethoxypyrrolidine. The compound of formula I is useful for the treatment or prophylaxis of sleep disorders.

  本发明涉及一种制备公式##STR1##的苯并[a]喹啉酮衍生物的过程，通过在羰基化催化剂和(S)-3-乙氧基吡咯烷或较低的烷基醇或水的存在下，将公式##STR2##的化合物（其中X为卤素，Ph为苯基）与一氧化碳反应。其中，已获得10-氯-6,7-二氢-4-氧代-3-苯基-4H-苯并[a]喹啉-1-羧酸的较低烷基酯，将其转化为相应的自由酸；并且，已获得10-氯-6,7-二氢-4-氧代-3-苯基-4H-苯并[a]喹啉-1-羧酸，将其反应的活性衍生物与(S)-3-乙氧基吡咯烷反应。公式I的化合物可用于治疗或预防睡眠障碍。
• (S)-1-[(10-chloro-6,7-dih
  申请人：Hoffmann-La Roche Inc.

  公开号：US05326769A1

  公开（公告）日：1994-07-05

  The compound (S)-1-[(10-chloro-6,7-dihydro-4-oxo-3-phenyl-4H-benzo[a]quino-lizin-1-yl)c arbonyl]-3-ethoxypyrrolidine of the formula ##STR1## which has valuable pharmacological properties, is described. In particular, the compound of formula I has a non-sedating, hypnotic, that is, sleep-promoting, activity and can accordingly be used for the treatment of sleep disorders.

  描述了一种具有有价值的药理学特性的化合物(S)-1-[(10-氯-6,7-二氢-4-氧代-3-苯基-4H-苯并[a]喹啉-1-基)羰基]-3-乙氧基吡咯烷的化合物，其化学式为##STR1##。特别是，化合物I具有非镇静、催眠作用，即促进睡眠的活性，因此可用于治疗睡眠障碍。
• A modified Bischler-Napieralski procedure for the synthesis of 3-aryl-3,4-dihydroisoquinolines
  作者：Robert D. Larsen、Robert A. Reamer、Edward G. Corley、Paul Davis、Edward J. J. Grabowski、Paul J. Reider、Ichiro Shinkai

  DOI：10.1021/jo00021a014

  日期：1991.10

  A modification of the Bischler-Napieralski reaction for the cyclization of (1,2-diphenylethyl)amides to the 3-aryl-3,4-dihydroisoquinolines is presented. Elimination of the amide group as the nitrile via the retro-Ritter reaction is avoided by its conversion to an N-acyliminium intermediate with oxalyl chloride-FeCl3. Removal of the oxalyl group in refluxing MeOH-sulfuric acid provides the 3,4-dihydroisoquinolines in moderate to high yields. The method is also highly effective with (2-phenylethyl)amides.
• An expedient route to the tricyclic pyridone derivative Ro 41-3696, a novel non-benzodiazepine sleep inducer
  作者：Paul R. Spurr

  DOI：10.1016/0040-4039(95)00387-r

  日期：1995.4

  A short, technical synthesis of (S)-10-chloro-1-(3-ethoxypyrrolidin-1-yl)-3-phenyl-6,7-dihydro-4H-benzo[a]-quinolizin-4-one (1) from 2-(4-chlorophenyl)ethylamine (2) is described.

  （S）-10-氯-1-（3-乙氧基吡咯烷-1-基）-3-苯基-6,7-二氢-4H-苯并[a]-喹啉--4-酮的简短技术合成（1）由2-（4-氯苯基）乙胺（2）描述。