methyl 6-methoxy-4-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate | 6271-18-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 6-methoxy-4-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate
• 英文别名: 6-methoxy-4-oxo-1,2,3,4-tetrahydro-[2]naphthoic acid methyl ester；6-Methoxy-4-oxo-1,2,3,4-tetrahydro-[2]naphthoesaeure-methylester；methyl 6-methoxy-4-oxo-2,3-dihydro-1H-naphthalene-2-carboxylate
• CAS: 6271-18-7
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: GOCGVSWHOIKTRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 6-methoxy-4-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate 在 Ru(II)-(1S,2S)-N-p-toluenesulfonyl-1,2-di-Ph-ethylenediamine lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 84.0h， 生成 (1S,3S)-3-(hydroxymethyl)-7-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol
  参考文献：
  名称：

  Kinetic resolution of 3-hydroxymethylbenzocycloalkanols by selective asymmetric hydrogen-transfer oxidation

  摘要：

  Kinetic resolution of 3-hydroxymethylbenzocycloalkanols was performed by selective asymmetric hydrogen-transfer oxidation using the Ru(II)-(S,S)-TsDPEN catalyst. Thus, several 3-hydroxymethyl-1-tetralols 7a-d afforded (1R,3R)-3-hydroxymethyl-1-tetralols (1R,3R)-7a-d and (S)-3-hydroxymethyl-1-tetralones (S)-9a-d, and 3-hydroxymethyl-1-indanol 7e gave (1R,3S)3-hydroxymethyl-1-indanol (1R,3S)-7e and (R)-3-hydroxymethyl-1-indanone (R)-9e, with high enantioselectivities. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.08.016
• 作为产物：
  描述：

  (+/-)-2-(4-methoxybenzyl)succinic acid 1-methyl ester 在 三氟乙酸 、 三氟乙酸酐 作用下， 反应 8.0h， 以50%的产率得到methyl 6-methoxy-4-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate
  参考文献：
  名称：

  Kinetic resolution of 3-hydroxymethylbenzocycloalkanols by selective asymmetric hydrogen-transfer oxidation

  摘要：

  Kinetic resolution of 3-hydroxymethylbenzocycloalkanols was performed by selective asymmetric hydrogen-transfer oxidation using the Ru(II)-(S,S)-TsDPEN catalyst. Thus, several 3-hydroxymethyl-1-tetralols 7a-d afforded (1R,3R)-3-hydroxymethyl-1-tetralols (1R,3R)-7a-d and (S)-3-hydroxymethyl-1-tetralones (S)-9a-d, and 3-hydroxymethyl-1-indanol 7e gave (1R,3S)3-hydroxymethyl-1-indanol (1R,3S)-7e and (R)-3-hydroxymethyl-1-indanone (R)-9e, with high enantioselectivities. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.08.016

文献信息

• Synthesis and analgetic activity of some benzomorphan analogs
  作者：Tadashi Kometani、Shunsaku Shiotani

  DOI：10.1021/jm00209a003

  日期：1978.11

  The benzomorphan analogues, 8-hydroxy-3-methyl-2,3,4,5-tetrahydro-1,4-methano-1H-3-benzazepine (1), 8-hydroxy-2-methyl-2,3,4,5-tetrahydro-1,4-methano-1H-2-benzazepine (2), 9-hydroxy-2-methyl-1,2,3,4,5,6-hexahydro-1,5,-methano-2-benzazocine (3), and 10-hydroxy-2-methyl-2,3,4,5,6,7-hexahydro-1,6-methano-1H-2-benzazonine (4), have been synthesized in order to evaluate their analgetic activity. Only slight

  苯并吗啡类似物8-hydroxy-3-methyl-2,3,4,5-tetrahydro-1,4-methano-1H-3-benzazepine（1），8-hydroxy-2-methyl-2,3,4 ，5-四氢-1,4-甲基-1H-2-苯并ze庚因（2），9-羟基-2-甲基-1,2,3,4,5,6-六氢-1,5，-甲基2合成了-benzazocine（3）和10-羟基-2-甲基-2,3,4,5,6,7-六氢-1,6-甲基-1H-2-benzazonine（4）评估其镇痛作用。在任何这些化合物中仅发现轻微的止痛活性。讨论了氮到芳香环距离对于止痛药-受体相互作用的重要性。