N-benzyl-3-phthalimidopropylamine | 95484-09-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-benzyl-3-phthalimidopropylamine
• 英文别名: N-<3-(Benzylamino)propyl>phthalimid；N-(phthalimidopropyl)benzylamine；2-(3-(benzylamino)propyl)isoindoline-1,3-dione；2-[3-(benzylamino)propyl]isoindole-1,3-dione
• CAS: 95484-09-6
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: MOMVTGBGFTXRIQ-UHFFFAOYSA-N

物化性质

• 沸点：
  455.0±28.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyl-3-phthalimidopropylamine 在 potassium fluoride 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 2-(3-(benzyl(3-(benzyl(4-(benzyl(4-(1,3-dioxoisoindolin-2-yl)butyl)amino)butyl)amino)propyl)amino)propyl)isoindoline-1,3-dione
  参考文献：
  名称：

  Niitsu, Masaru; Samejima, Keijiro, Chemical and pharmaceutical bulletin, 1986, vol. 34, # 3, p. 1032 - 1038

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(3-(benzhydryl(benzyl)amino)propyl)isoindoline-1,3-dione 在 乙醇 、 camphor-10-sulfonic acid 、 水 作用下， 反应 0.5h， 以99%的产率得到N-benzyl-3-phthalimidopropylamine
  参考文献：
  名称：

  Acidic Solvent-free Removal of Amine-protecting Diphenylmethyl Groups in the Presence of Camphorsulfonic Acid

  摘要：

  我们开发了去除二苯基甲基的新型反应条件，二苯基甲基是胺类最重要的保护基团之一。在水介质中加入一当量的樟脑磺酸即可促进反应，且无需酸性溶剂。

  DOI：

  10.1246/cl.170604

文献信息

• Synthese von selektivN- funktionalisierten Polyamin-Derivaten
  作者：Wolfgang J. Fiedler、Manfred Hesse

  DOI：10.1002/hlca.19930760412

  日期：1993.6.30

  Synthesis of Selectively N-Functionalized Polyamine Derivatives

  选择性N-官能化多胺衍生物的合成
• Syntheses of 15N-enriched polyamines.
  作者：KEIJIRO SAMEJIMA、YASUKO TAKEDA、MASAKO KAWASE、MASASHI OKADA、YOSHIMASA KYOGOKU

  DOI：10.1248/cpb.32.3428

  日期：——

  A total synthesis of polyamines was developed using potassium phthalimide as a sole nitrogen source. 15N-Enriched phthalimide was prepared almost quantitatively from 15N-enriched ammonium sulfate by a modified method. Key compounds for the synthesis of 15N-enriched spermidine and spermine were 15N-enriched putrescine (I), N-(3-bromopropyl)-phthalimide (II), N-(4-bromobutyl) phthalimide (III), and benzylamine, which were easily prepared in high yields from potassium 15N-enriched phthalimide. Spermidine was synthesized by two alternative methods involving an alkylation of monobenzyloxycarbonyl putrescine with II and a stepwise alkylation of benzylamine with II and III in the presence of KF-Celite. The lattter method allowed the preparation of all seven kinds of various 15N-enriched spermidines with combinations of the three reagents containing 15N or 14N. Spermine was similarly synthesized by an alkylation of N, N'-dibenzylputrescine with II. In these methods, the alkylation using KF-Celite was extremely useful for the synthesis of spermidine and spermine. The present methods were also used to synthesize various other polyamines in high yields.

  使用邻苯二甲酰亚胺钾作为唯一氮源开发了多胺的全合成。通过改进的方法，由富 15N 硫酸铵几乎定量地制备了 15N 富集邻苯二甲酰亚胺。合成 15N 富集亚精胺和精胺的关键化合物是 15N 富集腐胺 (I)、N-(3-溴丙基)-邻苯二甲酰亚胺 (II)、N-(4-溴丁基) 邻苯二甲酰亚胺 (III) 和苯甲胺，其中可以很容易地从富含 15N 的邻苯二甲酰亚胺钾中以高产率制备。亚精胺通过两种替代方法合成，包括在 KF-硅藻土存在下用 II 对单苄氧基羰基腐胺进行烷基化，以及用 II 和 III 对苄胺进行逐步烷基化。后一种方法允许通过含有15N或14N的三种试剂的组合来制备所有七种不同的富含15N的亚精胺。类似地，通过用II烷基化N,N'-二苄基腐胺来合成精胺。在这些方法中，使用 KF-Celite 进行烷基化对于亚精胺和精胺的合成非常有用。本方法还用于高产率合成各种其他多胺。
• Conjugates of Catecholamines. 5. Synthesis and β-Adrenergic Activity of N-(Aminoalkyl)norepinephrine Derivatives
  作者：Allen B. Reitz、Etienne Sonveaux、Roberto P. Rosenkranz、Michael S. Verlander、Kenneth L. Melmon、Brian B. Hoffman、Yasio Akita、Neal Castagnoli、Murray Goodman

  DOI：10.1021/jm50001a017

  日期：1985.5

  A novel series of N-aminoalkyl congeners and model derivatives of norepinephrine has been synthesized. Compounds that were structurally related to epinephrine were prepared from fully protected intermediates. Alternatively, isoproterenol-related compounds were synthesized via reductive amination of preformed methyl ketone derivatives with norepinephrine. The beta-adrenergic activities of these new compounds were assessed through measurement of intracellular cyclic AMP accumulation in S49 mouse lymphoma cells and displacement of iodocyanopindolol (ICYP) from membrane preparations. Congeners that contained an underivatized primary amine function exhibited virtually no activity in these assays. However, when this amine function was acylated (e.g., to an amide, carbamate, urea, sulfonamide, etc.), the products exhibited generally increased beta-adrenergic activity, which was, however, strongly dependent on the nature of the acylating group and also the length of the spacer. In particular, a benzyl carbamate derivative containing a branched, seven-carbon spacer group was 40 times more potent than isoproterenol in the in vitro S49 assay.
• EP0692982A4
  申请人：——

  公开号：EP0692982A4

  公开（公告）日：1998-03-11
• RADIOLABELED PLATELET GPIIb/IIIa RECEPTOR ANTAGONISTS AS IMAGING AGENTS FOR THE DIAGNOSIS OF THROMBOEMBOLIC DISORDERS
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：EP0692982A1

  公开（公告）日：1996-01-24