β-(1,2,3,4-Tetrahydro-2-methoxyamino-5-methoxy-3-naphthyl)-α-methylidene-propionic acid t.butyl ester | 103012-87-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: β-(1,2,3,4-Tetrahydro-2-methoxyamino-5-methoxy-3-naphthyl)-α-methylidene-propionic acid t.butyl ester
• 英文别名: Tert-butyl 2-[[8-methoxy-3-(methoxyamino)-1,2,3,4-tetrahydronaphthalen-2-yl]methyl]prop-2-enoate；tert-butyl 2-[[8-methoxy-3-(methoxyamino)-1,2,3,4-tetrahydronaphthalen-2-yl]methyl]prop-2-enoate
• CAS: 103012-87-9
• 化学式: C₂₀H₂₉NO₄
• 分子量: 347.455
• InChiKey: RDPLJWSTOJRFPK-UHFFFAOYSA-N

物化性质

• 沸点：
  455.0±55.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  β-(1,2,3,4-Tetrahydro-2-methoxyamino-5-methoxy-3-naphthyl)-α-methylidene-propionic acid t.butyl ester 在 sodium hydroxide 、 potassium dihydrogenphosphate 、 硫酸 作用下， 以 甲醇 为溶剂， 反应 79.0h， 生成 (+/-)-(3β,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-1,6-dimethoxy-3-(methoxycarbonyl)benzoquinoline
  参考文献：
  名称：

  Octahydrobenzo[g]quinolines: potent dopamine agonists which show the relationship between ergolines and apomorphine

  摘要：

  A synthesis of all four diastereoisomeric 3-(tert-butoxycarbonyl)-1,6-dimethoxyoctahydrobenzo[g]quinolines 13a-d is presented. The two trans isomers 13b and 13c have been converted to tricyclic analogues 20 (CV 205-502) and 26 (205-503) of the potent dopaminomimetic ergolines CQ 32-084 and pergolide, respectively. These two compounds combine the essential moiety of apomorphine with the important 8-substituents of ergolines. Preliminary pharmacological evaluation of 20 and 26 suggests that these novel dopamine agonists combine the specificity of apomorphine with the potency, long duration of action, and good oral activity of the ergolines.

  DOI：

  10.1021/jm00381a017
• 作为产物：
  描述：

  tert-butyl 3-<(1,2,3,4-tetrahydro-2-methoxyimino)-5-methoxy-3-naphthyl>-2-methylenepropionate 在 盐酸 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 生成 β-(1,2,3,4-Tetrahydro-2-methoxyamino-5-methoxy-3-naphthyl)-α-methylidene-propionic acid t.butyl ester
  参考文献：
  名称：

  Octahydrobenzo[g]quinolines: potent dopamine agonists which show the relationship between ergolines and apomorphine

  摘要：

  A synthesis of all four diastereoisomeric 3-(tert-butoxycarbonyl)-1,6-dimethoxyoctahydrobenzo[g]quinolines 13a-d is presented. The two trans isomers 13b and 13c have been converted to tricyclic analogues 20 (CV 205-502) and 26 (205-503) of the potent dopaminomimetic ergolines CQ 32-084 and pergolide, respectively. These two compounds combine the essential moiety of apomorphine with the important 8-substituents of ergolines. Preliminary pharmacological evaluation of 20 and 26 suggests that these novel dopamine agonists combine the specificity of apomorphine with the potency, long duration of action, and good oral activity of the ergolines.

  DOI：

  10.1021/jm00381a017

文献信息

• Novel pharmaceutically active 1,2,3,4,4a,5,10,10a-octahydrobenzo(g)quinoline derivatives
  申请人：SANDOZ AG

  公开号：EP0077754A2

  公开（公告）日：1983-04-27

  A 6- and/or 7-oxy-trans-1,2,3,4,4a,5,10,10a-octahydro- benzo[g]-quinoline in which the 3-position is substituted by an optionally amidated carboxy group, an optionally etherified hydroxymethyl group, a cyanomethyl group, an alkyl-or aryl-thiomethyl group or a sulfamoylamino or carbamoylamino group, or a physiologically-hydrolysable and -acceptable ester thereof. The subject compounds are useful as pharmaceuticals, in particular as prolactin secretion inhibitors, dopaminergic agents and dopamine receptor stimulating agents.

  一种 6-和/或 7-氧-反式-1,2,3,4,4a,5,10,10a-八氢-苯并[g]-喹啉，其中 3-位被任选酰胺化的羧基、任选醚化的羟甲基、氰甲基、烷基或芳基-硫甲基或氨基磺酰基或氨基甲酰基取代，或被其生理上可水解和可接受的酯取代。上述化合物可用作药物，特别是催乳素分泌抑制剂、多巴胺能制剂和多巴胺受体刺激剂。
• US4565818A
  申请人：——

  公开号：US4565818A

  公开（公告）日：1986-01-21