2-Diazo-1-(7-dipropylamino-5,6,7,8-tetrahydro-naphthalen-1-yl)-ethanone | 124688-31-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-Diazo-1-(7-dipropylamino-5,6,7,8-tetrahydro-naphthalen-1-yl)-ethanone
• 英文别名: (2Z)-2-diazo-1-[7-(dipropylamino)-5,6,7,8-tetrahydronaphthalen-1-yl]ethanone
• CAS: 124688-31-9
• 化学式: C₁₈H₂₅N₃O
• 分子量: 299.416
• InChiKey: BAGICMVGUMZBGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  22.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Diazo-1-(7-dipropylamino-5,6,7,8-tetrahydro-naphthalen-1-yl)-ethanone 、 甲醇 生成 methyl 2-[7-(dipropylamino)-5,6,7,8-tetrahydronaphthalen-1-yl]acetate
  参考文献：
  名称：

  KLINE, TONI B.;NELSON, DAVID L.;NAMBOODIRI, KRISHNAN, J. MED. CHEM., 33,(1990) N, C. 950-955

  摘要：

  DOI：
• 作为产物：
  描述：

  2-溴苯乙酰氯 在 platinum(IV) oxide 正丁基锂 、 三氯化铝 、 草酸氯化物 、 氢气 、 对甲苯磺酸 、 二环己胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 98.33h， 生成 2-Diazo-1-(7-dipropylamino-5,6,7,8-tetrahydro-naphthalen-1-yl)-ethanone
  参考文献：
  名称：

  Novel [(diazomethyl)carbonyl]-1,2,3,4-tetrahydronaphthalene derivatives as potential photoaffinity ligands for the 5-HT1A receptor

  摘要：

  The photolabile (diazomethyl)carbonyl function was introduced into the 8-position of 2-(N,N-di-n-propyl-amino)-1,2,3,4-tetrahydronaphthalene in three ways, resulting in the ether 8-[[(diazomethyl)carbonyl]methoxy]-2-(N,N-di-n-propylamino)-1,2,3,4- tetrahydronaphthalene (2), the ester 8-(diazoacetoxy)-2-(N,N-di-n-propyl-amino)-1,2,3,4- tetrahydronaphthalene (3), and the ketone 8-[(diazomethyl)carbonyl]-2-(N,N-di-n-propylamino)- 1,2,3,4-tetrahydronaphthalene (4). Specific binding of these compounds at the 5-hydroxytryptamine1A sites in rat brain membranes labeled with 1 nM [3H]-8-hydroxy-2-(N,N-di-n-propylamino)- 1,2,3,4-tetrahydronaphthalene (8-OH-DPAT) showed IC50 values of ca. 75, 125, and 25 nM, respectively, for the three compounds. Photolysis of methanolic solutions of 2-4 in the absence of receptor proteins lead in each case to an abundance of Wolff-rearranged products. In the case of ether 2, subsequent beta-elimination to 8-OH-DPAT removed this compound from serious consideration as a photoaffinity ligand. Ester 3 and ketone 4 were photolysed in vitro. Whereas ester 3 was ineffective in decreasing the specific binding of [3H]-8-OH-DPAT, ketone 4 decreased 40% of the specific binding of [3H]-8-OH-DPAT in the presence (but not the absence) of ultraviolet light. Thus this ketone emerges from these studies as a good candidate for a photoaffinity label for the 5-hydroxytrypatamine1A receptor.

  DOI：

  10.1021/jm00165a011

文献信息

• KLINE, TONI B.;NELSON, DAVID L.;NAMBOODIRI, KRISHNAN, J. MED. CHEM., 33,(1990) N, C. 950-955
  作者：KLINE, TONI B.、NELSON, DAVID L.、NAMBOODIRI, KRISHNAN

  DOI：——

  日期：——
• Novel [(diazomethyl)carbonyl]-1,2,3,4-tetrahydronaphthalene derivatives as potential photoaffinity ligands for the 5-HT1A receptor
  作者：Toni B. Kline、David L. Nelson、Krishnan Namboodiri

  DOI：10.1021/jm00165a011

  日期：1990.3

  The photolabile (diazomethyl)carbonyl function was introduced into the 8-position of 2-(N,N-di-n-propyl-amino)-1,2,3,4-tetrahydronaphthalene in three ways, resulting in the ether 8-[[(diazomethyl)carbonyl]methoxy]-2-(N,N-di-n-propylamino)-1,2,3,4- tetrahydronaphthalene (2), the ester 8-(diazoacetoxy)-2-(N,N-di-n-propyl-amino)-1,2,3,4- tetrahydronaphthalene (3), and the ketone 8-[(diazomethyl)carbonyl]-2-(N,N-di-n-propylamino)- 1,2,3,4-tetrahydronaphthalene (4). Specific binding of these compounds at the 5-hydroxytryptamine1A sites in rat brain membranes labeled with 1 nM [3H]-8-hydroxy-2-(N,N-di-n-propylamino)- 1,2,3,4-tetrahydronaphthalene (8-OH-DPAT) showed IC50 values of ca. 75, 125, and 25 nM, respectively, for the three compounds. Photolysis of methanolic solutions of 2-4 in the absence of receptor proteins lead in each case to an abundance of Wolff-rearranged products. In the case of ether 2, subsequent beta-elimination to 8-OH-DPAT removed this compound from serious consideration as a photoaffinity ligand. Ester 3 and ketone 4 were photolysed in vitro. Whereas ester 3 was ineffective in decreasing the specific binding of [3H]-8-OH-DPAT, ketone 4 decreased 40% of the specific binding of [3H]-8-OH-DPAT in the presence (but not the absence) of ultraviolet light. Thus this ketone emerges from these studies as a good candidate for a photoaffinity label for the 5-hydroxytrypatamine1A receptor.