N'-Carbo-tert-butoxy-N''-carbobenzoxyspermidine | 152754-73-9

• 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: N'-Carbo-tert-butoxy-N''-carbobenzoxyspermidine
• 英文别名: N⁸-benzyloxycarbonyl-N⁴-tert-butoxycarbonylspermidine；tert-butyl N-(3-aminopropyl)-N-[4-(phenylmethoxycarbonylamino)butyl]carbamate
• CAS: 152754-73-9
• 化学式: C₂₀H₃₃N₃O₄
• 分子量: 379.5
• InChiKey: WWHCSLXGPNUVEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  93.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N'-Carbo-tert-butoxy-N''-carbobenzoxyspermidine 在 sodium tetrahydroborate 、 sodium sulfate 作用下， 以 乙醇 为溶剂， 反应 28.0h， 生成 3-Butyl-N'''-carbobenzoxy-N,N''-dicarbo-tert-butoxythermospermine
  参考文献：
  名称：

  Synthesis of philanthotoxin analogs with a branched polyamine moiety

  摘要：

  Philanthotoxin (PhTX-433), a potent noncompetitive inhibitor of the L-glutamate receptors and the nicotinic acetylcholine receptors of vertebrates and invertebrates, has a butyryl-tyrosyl-thermo-spermine structure. Several synthetic analogs of PhTX with hydrophobic alkyl branches in the polyamine chain exhibit 6- to 10-fold enhanced activities to various receptors. Because the branched analogs exhibit such unique activities and because of their importance in tertiary structural studies of ligand/receptor binding, methods for preparing branched PhTX analogs, including photolabile analogs, are presented.

  DOI：

  10.1021/jo00076a017
• 作为产物：
  描述：

  N-(Carbobenzoxybutyl)-2-cyanoethylamine 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 N'-Carbo-tert-butoxy-N''-carbobenzoxyspermidine
  参考文献：
  名称：

  Synthesis of philanthotoxin analogs with a branched polyamine moiety

  摘要：

  Philanthotoxin (PhTX-433), a potent noncompetitive inhibitor of the L-glutamate receptors and the nicotinic acetylcholine receptors of vertebrates and invertebrates, has a butyryl-tyrosyl-thermo-spermine structure. Several synthetic analogs of PhTX with hydrophobic alkyl branches in the polyamine chain exhibit 6- to 10-fold enhanced activities to various receptors. Because the branched analogs exhibit such unique activities and because of their importance in tertiary structural studies of ligand/receptor binding, methods for preparing branched PhTX analogs, including photolabile analogs, are presented.

  DOI：

  10.1021/jo00076a017

文献信息

• Efficient Synthesis of Orthogonally Protected Spermidine and Norspermidine Derivatives
  作者：Ryszard Andruszkiewicz、Michał Radowski、Zbigniew Czajgucki

  DOI：10.1081/scc-200054211

  日期：2005.4.1

  Abstract Several orthogonally protected spermidine and norspermidine derivatives have been synthesized via cyanoethylation of monoprotected 1,4‐butanediamine (putrescine) or 1,3‐propanediamine followed by protection of their secondary amino groups and final reduction of the nitriles with lithium aluminum hydride in etheral solution at 0°C, thus affording protected norspermidine or spermidine that may

  摘要 通过单保护的 1,4-丁二胺（腐胺）或 1,3-丙二胺的氰乙基化，然后保护它们的仲氨基，最后在醚溶液中用氢化铝锂还原腈类，合成了几种正交保护的亚精胺和去甲精胺衍生物。在0°C，从而提供可用于合成多胺酰胺或可进一步官能化的受保护的去甲精胺或亚精胺。
• Synthesis of philanthotoxin analogs with a branched polyamine moiety
  作者：Aristotle G. Kalivretenos、Koji Nakanishi

  DOI：10.1021/jo00076a017

  日期：1993.11

  Philanthotoxin (PhTX-433), a potent noncompetitive inhibitor of the L-glutamate receptors and the nicotinic acetylcholine receptors of vertebrates and invertebrates, has a butyryl-tyrosyl-thermo-spermine structure. Several synthetic analogs of PhTX with hydrophobic alkyl branches in the polyamine chain exhibit 6- to 10-fold enhanced activities to various receptors. Because the branched analogs exhibit such unique activities and because of their importance in tertiary structural studies of ligand/receptor binding, methods for preparing branched PhTX analogs, including photolabile analogs, are presented.