N-(3-azidopropyl)-3-aminopropan-1-ol | 217454-49-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(3-azidopropyl)-3-aminopropan-1-ol
• 英文别名: 3-<(3-azidopropyl)amino>propan-1-ol；3-(3-Azidopropylamino)propan-1-ol
• CAS: 217454-49-4
• 化学式: C₆H₁₄N₄O
• 分子量: 158.203
• InChiKey: GQHVBFYMIKCQTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3-azidopropyl)-3-aminopropan-1-ol 在 4-二甲氨基吡啶 、 水 、 potassium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 三氟乙酸 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 sodium hydroxide 、 乙醚 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 230.5h， 生成 tert-butyl N-<9-allyl-16-<<3-(4-methoxyphenyl)prop-2-enoyl>amino>-13-<(2,2,2-trichloro-1,1-dimethylethoxy)carbonyl>-4-<2-(trimethylsilyl)ethylsulfonyl>-4,9,13-triazahexadecyl>carbamate
  参考文献：
  名称：

  Regioselective Deprotection and Acylation of Penta-N-Protected Thermopentamine

  摘要：

  The synthesis of the penta-N-protected polyamide 1 (ten-butyl N-{9-allyl-16-azido-13-(trinuoroacetyl)-4-[2-(trimethylsilyl)ethylsulfonyl]-4,9,13-triazahexadecyl]carbamate = tert-butyl N-{3-{[4-{allyl[3-[(3-azidopropyl)(trifluoroacetyl)aminopropyl}amino}butyl}{[2-(trimethylsilyl)ethyl]sulfonyl}amino}propyl}carbamate) is described, a derivative of thermopentamine (PA 3433) containing five independently removable amino-protecting groups. The selective deprotection of the five protecting groups used, it., of allyl, azido, (tert-butoxy)carbonyl (Boc). trifluoroacetyl, and [2-(trimethylsilyl)ethyl]sulfonyl (SES), as well as the rapid transamidation reaction of the trifluoroacetyl group yielding secondary amides is discussed. Subsequent acylation with 4-methoxycinnamoyl chloride at each N-atom of the pentamine backbone is achieved. For the acylation of the terminal N-atom the azido group is replaced by a (2,2,2-trichloro-1,l-dimethylethoxy)carbonyl (Tcboc) group.

  DOI：

  10.1002/(sici)1522-2675(19981216)81:12<2300::aid-hlca2300>3.0.co;2-7
• 作为产物：
  描述：

  3-氨基-1-丙醇 、 1-[(3-叠氮基丙氧基)磺酰基]-4-甲基苯 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 24.8h， 以86%的产率得到N-(3-azidopropyl)-3-aminopropan-1-ol
  参考文献：
  名称：

  Synthesis of Penta-N-Protected Homocaldopentamine and Its Selective Acylation

  摘要：

  The synthesis of the penta-N-protected polyamine homocaldopentamine {PA 4333, 1, tert-butyl N-[9-allyl-16-azido-13-(2,2,2-trichloro-tert-butoxycarbonyl)-5-(trimethylsilylethylsulfonyl)-5,9,13-triazahexadec-1-yl]carbamate}, containing five independent amino-protecting groups is described. These five protecting groups used-allyl, azido, tert-butoxycarbonyl (BOC), 2,2,2-trichloro-tert-butoxycarbonyl (TCBOC), and trimethylsilylethylsulfonyl (SES)-were removed selectively. The acylation with p-methoxycinnamoyl chloride at each nitrogen of the pentaamine was determined.

  DOI：

  10.1021/jo980689e

文献信息

• Regioselective Deprotection and Acylation of Penta-N-Protected Thermopentamine
  作者：Jae Kyoung Pak、Manfred Hesse

  DOI：10.1002/(sici)1522-2675(19981216)81:12<2300::aid-hlca2300>3.0.co;2-7

  日期：1998.12.16

  The synthesis of the penta-N-protected polyamide 1 (ten-butyl N-9-allyl-16-azido-13-(trinuoroacetyl)-4-[2-(trimethylsilyl)ethylsulfonyl]-4,9,13-triazahexadecyl]carbamate = tert-butyl N-3-[4-allyl[3-[(3-azidopropyl)(trifluoroacetyl)aminopropyl}amino}butyl}[2-(trimethylsilyl)ethyl]sulfonyl}amino}propyl}carbamate) is described, a derivative of thermopentamine (PA 3433) containing five independently removable amino-protecting groups. The selective deprotection of the five protecting groups used, it., of allyl, azido, (tert-butoxy)carbonyl (Boc). trifluoroacetyl, and [2-(trimethylsilyl)ethyl]sulfonyl (SES), as well as the rapid transamidation reaction of the trifluoroacetyl group yielding secondary amides is discussed. Subsequent acylation with 4-methoxycinnamoyl chloride at each N-atom of the pentamine backbone is achieved. For the acylation of the terminal N-atom the azido group is replaced by a (2,2,2-trichloro-1,l-dimethylethoxy)carbonyl (Tcboc) group.
• Synthesis of Penta-<i>N</i>-Protected Homocaldopentamine and Its Selective Acylation
  作者：Jae Kyoung Pak、Manfred Hesse

  DOI：10.1021/jo980689e

  日期：1998.11.1

  The synthesis of the penta-N-protected polyamine homocaldopentamine PA 4333, 1, tert-butyl N-[9-allyl-16-azido-13-(2,2,2-trichloro-tert-butoxycarbonyl)-5-(trimethylsilylethylsulfonyl)-5,9,13-triazahexadec-1-yl]carbamate}, containing five independent amino-protecting groups is described. These five protecting groups used-allyl, azido, tert-butoxycarbonyl (BOC), 2,2,2-trichloro-tert-butoxycarbonyl (TCBOC), and trimethylsilylethylsulfonyl (SES)-were removed selectively. The acylation with p-methoxycinnamoyl chloride at each nitrogen of the pentaamine was determined.