N-Dde-3-amino-1-propanol | 227758-39-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-Dde-3-amino-1-propanol
• 英文别名: N-1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl-3-aminopropan-1-ol；2-(1-((3-hydroxypropyl)amino)ethylidene)-5,5-dimethylcyclohexane-1,3-dione；Dde-β-alaninol；2-[1-(3-hydroxypropylamino)ethylidene]-5,5-dimethylcyclohexane-1,3-dione
• CAS: 227758-39-6
• 化学式: C₁₃H₂₁NO₃
• 分子量: 239.315
• InChiKey: ORMMLOXHMMAWTE-UHFFFAOYSA-N

物化性质

• 沸点：
  397.9±42.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.19
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  66.4
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-Dde-3-amino-1-propanol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以88%的产率得到1-bromo-3-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl)aminopropane
  参考文献：
  名称：

  正交保护的天然多胺的液相片段合成的一般方法及其应用。

  摘要：

  已经使用 α,ω-二胺和 ω-氨基醇分别作为 N-Cx-N 和 N-Cy 合成子合成了正交保护的多胺 (PA)，并且 Mitsunobu 反应是 PA 骨架组装的关键反应。Trt、Dde 和 Phth 基团已用于保护伯氨基功能，Ns 基团用于激活伯氨基功能以实现烷基化和仲氨基功能保护。该方法很容易扩展以适应蜘蛛毒素 Agel 416 和 HO-416b 的全合成，分别包含 3-4-3-3 和 3-3-3-4 PA 骨架。

  DOI：

  10.1021/acs.joc.9b02066
• 作为产物：
  描述：

  2-乙酰基-5,5-二甲基-1,3-环己二酮 、 3-氨基-1-丙醇 以 乙醇 为溶剂， 生成 N-Dde-3-amino-1-propanol
  参考文献：
  名称：

  Solid-phase synthesis of Agel 416; a novel approach to modified polyamines

  摘要：

  The synthesis of Agel 416, an acylpolyamine derived from the spider Agenolopsis aperta, has been achieved on solid support. Stepwise synthesis of the polyamine chain was accomplished using N-protected amino alcohols and the Fukuyama-Mitsunobu reaction. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)00995-3

文献信息

• Solid-Phase Synthesis, Hybridizing Ability, Uptake, and Nuclease Resistant Profiles of Position-Selective Cationic and Hydrophobic Phosphotriester Oligonucleotides
  作者：Luca Monfregola、Marvin H. Caruthers

  DOI：10.1021/acs.joc.5b01512

  日期：2015.9.18

  Analogues of oligonucleotides and mononucleotides with hydrophobic and/or cationic phophotriester functionalities often generate an improvement in target affinity and cellular uptake. Here we report the synthesis of phosphotriester oligodeoxyribonucleotides (ODNs) that are stable to the conditions used for their preparation. The method has been demonstrated by introducing phosphoramidite synthons where N-benzyloxycarbonyl (Z) protected amino alcohols replace the cyanoethyl group. After synthesis these ODNs were found to be stable to the condition required to remove base labile protecting groups and the ODNs from the solid support. Moreover the use of 1-(4,4-dimethyl-2, 6-dioxocyclohex-1-ylidene) ethyl (Dde) in place of Z protection on the amino alcohol has allowed us to introduce cationic aminoethyl phosphotriester modifications into ODNs. Melting temperatures of duplexes containing cationic or hydrophobic Z modified ODNs indicate that the backbone-phosphotriester modifications minimally affect duplex stability. Nuclease stability assays demonstrate that these phosphotriesters are resistant toward 5'- and 3'-exonudeases. Fluorescently labeled 23-mer ODNs modified with four cationic or hydrophobic Z phosphotriester linkages show efficient cellular uptake during passive transfection in HeLa and Jurkat cells.