2-(2-aminopropyl)-5,6,7,8-tetrahydronaphthalene | 3160-20-1

• 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-(2-aminopropyl)-5,6,7,8-tetrahydronaphthalene
• 英文别名: 2-<2-Amino-propyl>-5,6,7,8-tetrahydro-naphthalin；6-(2-Aminopropyl)tetralin；1-(5,6,7,8-tetrahydronaphthalen-2-yl)propan-2-amine
• CAS: 3160-20-1
• 化学式: C₁₃H₁₉N
• 分子量: 189.301
• InChiKey: UTVKUFYOPJCDPE-UHFFFAOYSA-N

物化性质

• 沸点：
  143-146 °C
• 密度：
  0.998±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2-aminopropyl)-5,6,7,8-tetrahydronaphthalene 在 palladium on activated charcoal 盐酸 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 戊醇 为溶剂， 生成 [1-Methyl-2-(5,6,7,8-tetrahydro-naphthalen-2-yl)-ethyl]-(tetrahydro-pyrimidin-2-ylidene)-amine; hydrochloride
  参考文献：
  名称：

  Guanidinium and amidinium fungicides: A new class of carbocation mimetic ergosterol biosynthesis inhibitors

  摘要：

  AbstractA novel class of chemical has been designed with the aim of inhibiting the Δ14‐reductase and Δ8‐Δ7‐isomerase enzymes in the ergosterol biosynthesis pathway in fungi. Use was made of knowledge about the mechanisms of both enzymes and the mode of action of known, fungicidal inhibitors of these enzymes. Pioneer examples have been synthesised and have been demonstrated to be potent inhibitors of ergosterol biosynthesis in Ustilago maydis (DC) Corda, acting in the same manner as the commercial fungicide fenpropimorph. They also showed excellent fungicidal activity against Erysiphe graminis DC f. sp. hordei Marchal (powdery mildew of barley) and Puccinia recondita Rob. ex Desm. (wheat leaf rust) in in‐vivo glasshouse tests. Using these compounds as a starting point, systematic structural variation has been carried out. Testing of a wide range of analogues at high volume confirms the potential of this class of compound to control mildew and rust pathogens at levels comparable to those of the standards. Correlation of in‐vivo and enzymatic data is good and the structure‐activity relationship developed for this series of compounds closely parallels that found for the morpholine/piperidine class of fungicides, suggesting a common mode of action.

  DOI：

  10.1002/ps.2780440406
• 作为产物：
  描述：

  2-<5.6.7.8-Tetrahydro-naphthyl-(2)>-3-oxo-butyronitril 在 镍 盐酸 、 氨 、 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 生成 2-(2-aminopropyl)-5,6,7,8-tetrahydronaphthalene
  参考文献：
  名称：

  Hydrierte Derivate von Benz[f]- und Benz[g]isochinolinen

  摘要：

  DOI：

  10.1007/bf00912289

文献信息

• Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogs of 3,4-(methylenedioxy)amphetamine
  作者：Aaron P. Monte、Danuta Marona-Lewicka、Nicholas V. Cozzi、David E. Nichols

  DOI：10.1021/jm00075a027

  日期：1993.11

  benzofuran and indan analogs 4-6 produced similar discriminative cues, whereas the tetralin derivative 7 did not fully substitute for the training drugs. The results in the in vitro pharmacology studies indicate that selectivity for 5-HT versus catecholamine uptake carriers may be modulated by the position and orientation of ring oxygen atoms. However, the nonoxygenated isostere 6 possessed high potency

  制备3,4-（亚甲基二氧基）苯丙胺（MDA）的苯并呋喃，茚满和四氢萘类似物，以检查MDA的二氧杂环戊环氧原子在与5-羟色胺和儿茶酚胺摄取载体相互作用中的作用。评估了该系列化合物对受过训练的大鼠的歧视性刺激作用，这些大鼠从训练药物（S）-（+）-MBDB（1c），MMAI（3）和（S）-（+）-苯异丙胺中区分出盐水，并针对具有抑制[3H] 5-羟色胺，[3H]多巴胺和[3H]去甲肾上腺素向粗突触体制剂中摄取的能力。从行为上讲，苯并呋喃和茚满类似物4-6产生相似的判别线索，而四氢化萘衍生物7不能完全替代训练药物。体外药理研究的结果表明，5-HT对儿茶酚胺摄取载体的选择性可能受环氧原子的位置和方向的调节。但是，未氧化的等位异构体6在所有检查的摄取位点均具有高效力。饱和环被一个亚甲基单元扩大以得到四氢化萘衍生物，导致儿茶酚胺位点的活性大大降低（3-4倍）。
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