N-(1-phenylpentyl)-N-propylamine | 72961-56-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(1-phenylpentyl)-N-propylamine
• 英文别名: 1-phenyl-N-propylpentan-1-amine
• CAS: 72961-56-9
• 化学式: C₁₄H₂₃N
• 分子量: 205.343
• InChiKey: RVYHYIYMMSSJTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  N-(1-phenylpentyl)-N-propylamine 、 2-methoxy-4-chlorobenzoyl thioisocyanate 在 sodium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Rational Design, Synthesis, and Structure−Activity Relationships of Aryltriazoles as Novel Corticotropin-Releasing Factor-1 Receptor Antagonists

  摘要：

  Following the discovery of the very high binding affinity of 4-anilinopyrimidines against corticotropin-releasing factor receptor-1 (CRF1) (e.g., 1, K-i = 2 nM), a new series of triazoles bearing different groups has been synthesized and evaluated. The compounds were prepared by cyclizations of N-acyl-S-methylisothioureas with alkylhydrazines or by cyclizations with hydrazine followed by alkylation. While members of this series showed potent binding affinity against CRF1 receptor, there were important differences between the different regio- (7 and 12) and stereoisomeric aryltriazoles where the R-1 or R-2 side chain in 7 has an asymmetric center. In terms of overall potency, aryltriazole analogues such as 7r bearing an N-(alpha-branched benzyl)-N-propylamino side chain were the most potent, followed by analogues such as 7a, with an N-bis(cyclopropyl)methyl-N-propylamino side chain, and analogues such as 7m, with an N-(alpha-branched aliphatic)-N-propylamino side chain. While the N-propyl group was crucial for high potency, we hypothesized that the terminal methyl mimicked the 5-methyl of pyrazolo[1,5-alpha]pyrimidines 3 and 4. Correlation of the low-energy conformers of compounds of type 3 and 7 generated by computational analyses was very good. The size and shape of the N-alkyl group dramatically changed the potency of the triazoles, which is in contrast to the SAR seen for bicyclic CRF1 antagonists. In general, the S-enantiomer was much more potent than the corresponding R-isomer. Furthermore, to a limited extent in the aryltriazole series the substituent on the 5-phenyl ring changed the potency up to 9-fold. (S)-1-Methyl-3-[N-(4-fluorophenylpentyl)-N-propyl]amino-5-(2-methoxy-4-dichlorophenyl)-1H-[1,2,4]triazole [(S)-7r] showed very potent binding affinity (K-i = 2.7 nM) to CRF1 receptors with an IC50 of 49 nM in a cAMP inhibition assay.

  DOI：

  10.1021/jm049339c
• 作为产物：
  描述：

  反式-1-苯基-2-戊烯-1-酮 、 丙腈 以37%的产率得到
  参考文献：
  名称：

  KOZLOV N. S.; MOJSEENOK L. I.; KOZINTSEV S. I., DOKL. AN BSSR, 1979, 23, HO 11, 1006-1009

  摘要：

  DOI：

文献信息

• Regioselective Preparation of 2-Phenylethylamines from 1-Phenyl-2-alkyl­alkynes by Hydroamination/Reduction Sequences
  作者：Sven Doye、Andreas Heutling、René Severin

  DOI：10.1055/s-2004-834863

  日期：——

  Ind2TiMe2 is a highly active and general catalyst for the intermolecular hydroamination of alkynes. Particularly impressive is that Ind2TiMe2 makes it possible to perform hydroamination reactions of unsymmetrically substituted 1-phenyl-2-alkylalkynes with primary aryl-, tert-alkyl-, sec-alkyl-, and n-alkylamines in a highly regioselective fashion. Since the initially formed imines can easily be reduced with zinc-modified NaBH3CN, 2-phenylethylamines are accessible in reliable one-pot procedures from 1-phenyl-2-alkylalkynes and primary amines on a 10 mmol scale.

  Ind2TiMe2 是炔烃分子间氢化反应的高活性通用催化剂。尤其令人印象深刻的是，Ind2TiMe2 能够以高度区域选择性的方式使不对称取代的 1-苯基-2-烷基炔与伯芳基、叔烷基、仲烷基和正烷基胺发生氢化反应。由于最初形成的亚胺可以很容易地用锌改性的 NaBH3CN 还原，因此可以在 10 毫摩尔的规模上通过可靠的一锅法从 1-苯基-2-烷基炔和伯胺中获得 2-苯基乙胺。
• Rational Design, Synthesis, and Structure−Activity Relationships of Aryltriazoles as Novel Corticotropin-Releasing Factor-1 Receptor Antagonists
  作者：Richard F. Lowe、Jodene Nelson、Trunghau N. Dang、Paul D. Crowe、Anil Pahuja、James R. McCarthy、Dimitri E. Grigoriadis、Paul Conlon、John Saunders、Chen、Thomas Szabo、Ta Kung Chen、Haig Bozigian

  DOI：10.1021/jm049339c

  日期：2005.3.1

  Following the discovery of the very high binding affinity of 4-anilinopyrimidines against corticotropin-releasing factor receptor-1 (CRF1) (e.g., 1, K-i = 2 nM), a new series of triazoles bearing different groups has been synthesized and evaluated. The compounds were prepared by cyclizations of N-acyl-S-methylisothioureas with alkylhydrazines or by cyclizations with hydrazine followed by alkylation. While members of this series showed potent binding affinity against CRF1 receptor, there were important differences between the different regio- (7 and 12) and stereoisomeric aryltriazoles where the R-1 or R-2 side chain in 7 has an asymmetric center. In terms of overall potency, aryltriazole analogues such as 7r bearing an N-(alpha-branched benzyl)-N-propylamino side chain were the most potent, followed by analogues such as 7a, with an N-bis(cyclopropyl)methyl-N-propylamino side chain, and analogues such as 7m, with an N-(alpha-branched aliphatic)-N-propylamino side chain. While the N-propyl group was crucial for high potency, we hypothesized that the terminal methyl mimicked the 5-methyl of pyrazolo[1,5-alpha]pyrimidines 3 and 4. Correlation of the low-energy conformers of compounds of type 3 and 7 generated by computational analyses was very good. The size and shape of the N-alkyl group dramatically changed the potency of the triazoles, which is in contrast to the SAR seen for bicyclic CRF1 antagonists. In general, the S-enantiomer was much more potent than the corresponding R-isomer. Furthermore, to a limited extent in the aryltriazole series the substituent on the 5-phenyl ring changed the potency up to 9-fold. (S)-1-Methyl-3-[N-(4-fluorophenylpentyl)-N-propyl]amino-5-(2-methoxy-4-dichlorophenyl)-1H-[1,2,4]triazole [(S)-7r] showed very potent binding affinity (K-i = 2.7 nM) to CRF1 receptors with an IC50 of 49 nM in a cAMP inhibition assay.
• KOZLOV N. S.; MOJSEENOK L. I.; KOZINTSEV S. I., DOKL. AN BSSR, 1979, 23, HO 11, 1006-1009
  作者：KOZLOV N. S.、 MOJSEENOK L. I.、 KOZINTSEV S. I.

  DOI：——

  日期：——