N⁴-Benzyl-N¹-(tert-butoxycarbonyl)norspermidine | 90914-13-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N⁴-Benzyl-N¹-(tert-butoxycarbonyl)norspermidine
• 英文别名: N4-benzyl-N1-(t-butoxycarbonyl)norspermidine；tert-butyl N-[3-[3-aminopropyl(benzyl)amino]propyl]carbamate
• CAS: 90914-13-9
• 化学式: C₁₈H₃₁N₃O₂
• 分子量: 321.463
• InChiKey: GAGBUVQPYMYCJV-UHFFFAOYSA-N

物化性质

• 沸点：
  451.0±30.0 °C(Predicted)
• 密度：
  1.034±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  67.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N⁴-Benzyl-N¹-(tert-butoxycarbonyl)norspermidine 在 potassium fluoride 、 sodium tetrahydroborate 、 Celite 、 magnesium sulfate 、 三乙胺 、 三氟乙酸 、 肼 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  摘要：

  Purpose. Twelve synthetic spider toxin analogs were prepared in an effort to better understand the structure-activity relationships of the polyamine portion of argiotoxin-636 (Arg-636), a noncompetitive NMDA receptor (NMDAR) antagonist.Methods. The 1,13-diamino-4,8-diazatridecane portion of the side chain of Arg-636 was systematically modified in an effort to further our knowledge of the structural requirements for the alkyl linker spacing between the amine nitrogens. Systematic isosteric replacement of each of the amine nitrogens in the polyamine moiety with either oxygen or carbon provided a series of compounds which were evaluated in vitro for NMDAR antagonist activity.Results. One-half of the heteroatoms found in Arg-636 were removed to provide analogs which maintained in vitro potency below 1 mu M. However, these simplified analogs produced similar or more pronounced effects on the cardiovascular system than Arg-636 in vivo.Conclusions. In this set of analogs, a minimum of three basic nitrogens in the side chain was required for maximum potency as NMDAR antagonists. Isosteric nitrogen substitutions in the polyamine chain reduced the in vitro potency of these analogs. An analog binding-conformation model was proposed to rationalize the inactivity of these isosterically substituted analogs.

  DOI：

  10.1023/a:1011988317683
• 作为产物：
  描述：

  3-苄胺基丙胺 在 镍 sodium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 100.0 ℃ 、275.79 kPa 条件下， 反应 32.0h， 生成 N⁴-Benzyl-N¹-(tert-butoxycarbonyl)norspermidine
  参考文献：
  名称：

  Reagents for the stepwise functionalization of spermidine, homospermidine, and bis(3-aminopropyl)amine

  摘要：

  DOI：

  10.1021/jo00190a028

文献信息

• Total Synthesis of Vulnibactin: A Natural Product Iron Chelator
  作者：Raymond Bergeron、Neelam Bharti、Shailendra Singh

  DOI：10.1055/s-2007-965960

  日期：2007.4

  A short, high-yield, flexible synthesis is described for accessing vulnibactin and related siderophores, e.g., vibriobactin analogues and homologues. The spectral properties of the synthetic vulnibactin are identical with those reported for the natural product, thus confirming the proposed structure of vulnibactin.

  本文描述了一种简短、高产、灵活的合成方法，可用于获得硫杆菌素和相关的苷元，如弧菌素类似物和同系物。合成的硫杆菌素的光谱特性与天然产物的光谱特性相同，从而证实了硫杆菌素的拟议结构。
• Total synthesis of vibriobactin
  作者：R.J. Bergeron、J.R. Garlich、J.S. McManis

  DOI：10.1016/s0040-4020(01)96492-0

  日期：1985.1