N-butyl-1,2,3,4-tetrahydronaphthalen-2-amine | 19485-88-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: N-butyl-1,2,3,4-tetrahydronaphthalen-2-amine
• 英文别名: N-butyl-1,2,3,4-tetrahydro-2-naphthylamine；butyl-(1,2,3,4-tetrahydro-[2]naphthyl)-amine；Butyl-(1,2,3,4-tetrahydro-[2]naphthyl)-amin；2-Butylamino-1,2,3,4-tetrahydro-naphthalin
• CAS: 19485-88-2
• 化学式: C₁₄H₂₁N
• mdl: MFCD12146346
• 分子量: 203.327
• InChiKey: FSXXDNPGFQZQSR-UHFFFAOYSA-N

物化性质

• 沸点：
  118-125 °C(Press: 2 Torr)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 N-butyl-1,2,3,4-tetrahydronaphthalen-2-amine 在 甲酸 、 水 作用下， 生成 2-(N-Butyl-N-methyl)-amino-1,2,3,4-tetrahydro-naphthalene
  参考文献：
  名称：

  Cymerman Craig et al., Australian Journal of Chemistry, 1959, vol. 12, p. 447,450,451

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(1,2,3,4-tetrahydro-[2]naphthyl)-butyramide 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 N-butyl-1,2,3,4-tetrahydronaphthalen-2-amine
  参考文献：
  名称：

  Cymerman Craig et al., Australian Journal of Chemistry, 1959, vol. 12, p. 447,450,451

  摘要：

  DOI：

文献信息

• Radical cyclisations of imines and hydrazones
  作者：W. Russell Bowman、Peter T. Stephenson、Nicholas K. Terrett、Adrian R. Young

  DOI：10.1016/0040-4020(95)00412-2

  日期：1995.7

  Radical cyclisation of sp3 carbon-centred radicals onto imines and hydrazones provides a new method for the synthesis of 5- and 6-membered ring nitrogen heterocycles. Cyclisation onto the electrophilic carbon of the C=N group and 5-exo stereoelectronic selectivity are the dominating mechanistic parameters. The C-centred radical intermediates were generated from benzeneselenyl precursors using Bu3SnH

  sp 3碳中心自由基在亚胺和上的自由基环化为合成5和6元环氮杂环提供了一种新方法。到C = N基团的亲电子碳上的环化和5 exo立体电子选择性是主要的机械参数。使用Bu 3 SnH由苯硒基前体生成C中心自由基中间体。
• Comparison of biological effects of N-alkylated congeners of .beta.-phenethylamine derived from 2-aminotetralin, 2-aminoindan, and 6-aminobenzocycloheptene
  作者：Joseph G. Cannon、Julio A. Perez、Jonathan P. Pease、John Paul Long、Jan R. Flynn、David B. Rusterholz、Stuart E. Dryer

  DOI：10.1021/jm00181a009

  日期：1980.7

  semirigid congeners of beta-phenethylamine have been prepared for evaluation of the effect of ring size (and of concomitant conformational variation) on biological activity in a variety of assays for adrenergic and dopaminergic actions. Pharmacologic activity was associated with 2-aminotetralin and 2-aminoindan derivateves, but was not found with 6-aminobenzocycloheptene derivatives. Noteworthy is the

  已经准备了三个系列的β-苯乙胺双环，半刚性同源物，用于评估在各种肾上腺素能和多巴胺能作用的测定中环大小（以及伴随的构象变化）对生物活性的影响。药理活性与2-氨基四氢萘和2-氨基茚满衍生物有关，但与6-氨基苯并环庚烯衍生物未发现。值得注意的是几种氨基四氢化萘和氨基茚满在不引起多巴胺能作用的情况下增加热板反应时间的能力。纳洛酮预处理不阻止该作用。
• Domino Hydrogenation–Reductive Amination of Phenols, a Simple Process To Access Substituted Cyclohexylamines
  作者：Varsha R. Jumde、Elena Petricci、Chiara Petrucci、Niccolò Santillo、Maurizio Taddei、Luigi Vaccaro

  DOI：10.1021/acs.orglett.5b01842

  日期：2015.8.21

  Phenols can be efficiently reduced by sodium formate and Pd/C as the catalyst in water and in the presence of amines to give the corresponding cydohexylamines. This reaction works at rt for 12 h or at 60 degrees C under mictowave dielectric heating for 20 min. With the exception of aniline, primary, secondary amines, amino alcohols, and even amino acids can be used as nucleophiles. The reductive process is based on a sustainable hydrogen source and a catalyst that can be efficiently recovered and reused. The protocol was developed into a continuous-flow production of cyclohexyl-amines in gram scale achieving very efficient preliminary results (TON 32.7 and TOF 5.45 h(-1)).
• Synthesis and pharmacology of some 2-aminotetralins. Dopamine receptor agonists
  作者：John D. McDermed、Gerald M. McKenzie、Arthur P. Phillips

  DOI：10.1021/jm00238a008

  日期：1975.4

  A series of 2-amino-1,2,3,4-tetrahydronaphthalene compounds bearing substituents on the nitrogen and in the aromatic ring was synthesized from beta-tetralone intermediates. Compounds were screened in vivo for dopaminergic activity using tests in which apomorphine was especially active. It was found that apparent dopaminergic activity is inherent in 2-dialkylaminotetralins, the dipropylamine substitution being the most consistently productive amine group studies. Activity was greatly enhanced by proper substitution in the aromatic ring. The 5,6-dihydroxy group was the best potentiating group found. These data support the idea that the extended conformation for the phenylethylamine moiety of ampmorphine and dopamine is favorable for dopaminergic agonist activity. They also suggest that an unetherified catechol group may not be essential for such activity.
• Voigtlaender, Pharmazie, 1959, vol. 14, p. 318,319
  作者：Voigtlaender

  DOI：——

  日期：——