1-acetamido-5,8-dihydronaphthalene | 115348-05-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-acetamido-5,8-dihydronaphthalene
• 英文别名: N-(5,8-dihydro-[1]naphthyl)-acetamide；N-(5,8-Dihydro-[1]naphthyl)-acetamid；Acetamide, N-(5,8-dihydro-1-naphthalenyl)-；N-(5,8-dihydronaphthalen-1-yl)acetamide
• CAS: 115348-05-5
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: CDKRCIMZWMKNRM-UHFFFAOYSA-N

物化性质

• 沸点：
  373.7±31.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-acetamido-5,8-dihydronaphthalene 在 sodium periodate 、 四氧化锇 、 sodium ethanolate 、 草酸 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 N-[2-(1H-吲哚-4-基)乙基]-N-丙基丙-1-胺
  参考文献：
  名称：

  Preliminary evaluation of 4-(2-N,N-dialkylaminoethyl)indoles as potential dopamine agonists

  摘要：

  DOI：

  10.1016/0223-5234(91)90110-9
• 作为产物：
  描述：

  1-萘胺 在 氨 、 sodium 作用下， 以 乙醚 、 叔丁醇 、 苯 为溶剂， 反应 1.0h， 生成 1-acetamido-5,8-dihydronaphthalene
  参考文献：
  名称：

  Synthesis, in vitro acetylcholine-storage-blocking activities, and biological properties of derivatives and analogs of trans-2-(4-phenylpiperidino)cyclohexanol (vesamicol)

  摘要：

  Eighty-four analogues and derivatives of the acetylcholine-storage-blocking drug trans-2-(4-phenylpiperidino)-cyclohexanol (vesamicol) were synthesized, and their potencies were evaluated with the acetylcholine active-transport assay utilizing purified synaptic vesicles from Torpedo electric organ. The parent drug exhibits enantioselectivity, with (-)-vesamicol being 25-fold more potent than (+)-vesamicol. The atomic structure and absolute configuration of (+)-vesamicol were determined by X-ray crystallography. The absolute configuration of (-)-vesamicol is 1R,2R. Structure-activity evidence indicates that (-)-vesamicol does not act as an acetylcholine analogue. Alterations to all three rings can have large effects on potency. Unexpectedly, analogues locking the alcohol and ammonium groups trans-diequatorial or trans-diaxial both exhibit good potency. A potent benzovesamicol family has been discovered that is suitable for facile elaboration of the sort useful in affinity labeling and affinity chromatography applications. A good correlation was found between potencies as assessed by the acetylcholine transport assay and LD50 values in mouse.

  DOI：

  10.1021/jm00126a013

文献信息

• 10.1002/anie.202407392
  作者：Li, Hao、Li, Yan、Chen, Jiaye、Lu, Lijun、Wang, Pengjie、Hu, Jingcheng、Ma, Rui、Gao, Yiming、Yi, Hong、Li, Wu、Lei, Aiwen

  DOI：10.1002/anie.202407392

  日期：——

  An electrochemical approach for the selective hydrogenation of aromatic hydrocarbons has been proposed. Detailed mechanistic studies indicate that the selectivity is attributed to combined effects of in situ released protons during anodic oxidation and significant differences in H+ mobility among various solvents.

  提出了一种芳香烃选择性加氢的电化学方法。详细的机理研究表明，选择性归因于阳极氧化过程中原位释放的质子的综合作用以及各种溶剂之间 H +迁移率的显着差异。
• Plieninger; Suhr, Chemische Berichte, 1956, vol. 89, p. 270,277
  作者：Plieninger、Suhr

  DOI：——

  日期：——
• Rowe; Davies, Journal of the Chemical Society, 1922, vol. 121, p. 1006
  作者：Rowe、Davies

  DOI：——

  日期：——
• Synthesis, in vitro acetylcholine-storage-blocking activities, and biological properties of derivatives and analogs of trans-2-(4-phenylpiperidino)cyclohexanol (vesamicol)
  作者：Gary A. Rogers、Stanley M. Parsons、D. C. Anderson、Lena M. Nilsson、Ben A. Bahr、Wayne D. Kornreich、Rose Kaufman、Robert S. Jacobs、Bernard Kirtman

  DOI：10.1021/jm00126a013

  日期：1989.6

  Eighty-four analogues and derivatives of the acetylcholine-storage-blocking drug trans-2-(4-phenylpiperidino)-cyclohexanol (vesamicol) were synthesized, and their potencies were evaluated with the acetylcholine active-transport assay utilizing purified synaptic vesicles from Torpedo electric organ. The parent drug exhibits enantioselectivity, with (-)-vesamicol being 25-fold more potent than (+)-vesamicol. The atomic structure and absolute configuration of (+)-vesamicol were determined by X-ray crystallography. The absolute configuration of (-)-vesamicol is 1R,2R. Structure-activity evidence indicates that (-)-vesamicol does not act as an acetylcholine analogue. Alterations to all three rings can have large effects on potency. Unexpectedly, analogues locking the alcohol and ammonium groups trans-diequatorial or trans-diaxial both exhibit good potency. A potent benzovesamicol family has been discovered that is suitable for facile elaboration of the sort useful in affinity labeling and affinity chromatography applications. A good correlation was found between potencies as assessed by the acetylcholine transport assay and LD50 values in mouse.
• Preliminary evaluation of 4-(2-N,N-dialkylaminoethyl)indoles as potential dopamine agonists
  作者：PE Persons、JP Mayer、DE Nichols、JM Cassady、EB Smalstig、JA Clemens

  DOI：10.1016/0223-5234(91)90110-9

  日期：1991.6