2-acetamido-6-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one | 66361-78-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-acetamido-6-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one
• 英文别名: N-(1-oxo-6-phenylmethoxy-3,4-dihydro-2H-naphthalen-2-yl)acetamide
• CAS: 66361-78-2
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: DQAWVCZLLDOURS-UHFFFAOYSA-N

物化性质

• 熔点：
  156-158 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  575.6±50.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-acetamido-6-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 sodium hydride 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 甲醚 、 乙二醇 为溶剂， 反应 4.0h， 生成 (4aS,10bS)-8-Benzyloxy-4-ethyl-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazine
  参考文献：
  名称：

  Synthesis of 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, a new class of dopamine agonists

  摘要：

  A series of tricyclic oxazines, namely, the 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, have been synthesized and assayed for dopamine agonist activity. One of the members of this series, compound (+)VII-15, was found to be a remarkably potent agonist in vivo when tested in the standard 6-hydroxydopamine lesioned rat assay. The absolute configuration of the compound corresponds to that found in the active isomer of apomorphine. Its activity at the alpha 2 receptor (vs. [3H]clonidine) is relatively low. It also failed to stimulate the synthesis of cAMP in the carp retina assay, thus giving the compound a highly selective profile in favor of the D2 receptor.

  DOI：

  10.1021/jm00378a014
• 作为产物：
  描述：

  3,4-二氢-6-(苯基甲氧基)-1(2H)-萘酮 在 potassium tert-butylate 、 锌 、 亚硝酸异戊酯 作用下， 以 乙醚 、 溶剂黄146 、 正丁醇 为溶剂， 反应 4.5h， 生成 2-acetamido-6-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  Synthesis of 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, a new class of dopamine agonists

  摘要：

  A series of tricyclic oxazines, namely, the 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, have been synthesized and assayed for dopamine agonist activity. One of the members of this series, compound (+)VII-15, was found to be a remarkably potent agonist in vivo when tested in the standard 6-hydroxydopamine lesioned rat assay. The absolute configuration of the compound corresponds to that found in the active isomer of apomorphine. Its activity at the alpha 2 receptor (vs. [3H]clonidine) is relatively low. It also failed to stimulate the synthesis of cAMP in the carp retina assay, thus giving the compound a highly selective profile in favor of the D2 receptor.

  DOI：

  10.1021/jm00378a014

文献信息

• Synthesis and conformational analysis of 2-amino-1,2,3,4-tetrahydro-1-naphthalenols
  作者：Antonio Delgado、José Miguel Garcia、David Mauleon、Cristina Minguillon、Joan Ramon Subirats、Miguel Feliz、Francisco Lopez、Dolores Velasco

  DOI：10.1139/v88-088

  日期：1988.3.1

  followed by reduction of the intermediate hydroxyimino tetralone and (or) Neber rearrangement of the tosyloxy derivatives 7a–e. Stereoselective reduction of the C(1) carbonyl group of acetamidotetralones 5a–e or aminotetralones 8a–e afforded the corresponding acetamido or aminotetralols, respectively, of OH/N trans stereochemistry whereas an opposite stereoselectivity was observed in reduction of C(8)-OCH3

  描述了几种顺式和（或）反式-2-氨基-1,2,3,4-四氢-1-萘酚的合成和构象分析。在起始四氢萘酮 3 的 C(2) 位置引入氮原子是通过亚硝化然后还原中间体羟基亚氨基四氢萘酮和（或）甲苯磺酰氧基衍生物 7a-e 的 Neber 重排进行的。乙酰氨基四氢萘酮 5a-e 或氨基四氢萘酮 8a-e 的 C(1) 羰基的立体选择性还原分别提供相应的 OH/N 反式立体化学的乙酰氨基或氨基四醇，而在 C(8)-OCH3 的还原中观察到相反的立体选择性导数 5f 和 8f 在相同的实验条件下。最后，反式乙酰氨基四醇的酸水解导致高产率的顺式氨基醇。已通过1H核磁共振技术和MM2理论计算进行了构象分析。所有顺式衍生物都显示出一个主要的构象，其中 C(1)-OH 基...
• JONES, J. H.;ANDERSON, P. S.;BALDWIN, J. J.;CLINESCHMIDT, B. V.;MCCLURE, +, J. MED. CHEM., 1985, 27, N 12, 1607-1613
  作者：JONES, J. H.、ANDERSON, P. S.、BALDWIN, J. J.、CLINESCHMIDT, B. V.、MCCLURE, +

  DOI：——

  日期：——
• DELGADO, ANTONIO;MIGUEL, GARCIA JOS;MAULEON, DAVID;MINGUILLON, CRISTINA;R+, CAN. J. CHEM., 66,(1988) N 3, 517-527
  作者：DELGADO, ANTONIO、MIGUEL, GARCIA JOS、MAULEON, DAVID、MINGUILLON, CRISTINA、R+

  DOI：——

  日期：——