N,N'-dipentyl-1,6-hexanediamine | 116435-58-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N'-dipentyl-1,6-hexanediamine
• 英文别名: N,N'-dipentylhexane-1,6-diamine；N,N'-dipentyl-hexanediyldiamine；N,N'-Dipentyl-hexandiyldiamin
• CAS: 116435-58-6
• 化学式: C₁₆H₃₆N₂
• 分子量: 256.475
• InChiKey: VXXSNHUQASULIX-UHFFFAOYSA-N

物化性质

• 沸点：
  331.3±10.0 °C(Predicted)
• 密度：
  0.826±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N'-dipentyl-1,6-hexanediamine 在 氧化亚氮 作用下， 以 乙腈 为溶剂， 反应 22.0h， 以46.4%的产率得到(Z)-1-{N-pentyl-N-[6-(N-pentylammoniohexyl)amino]}diazen-1-ium-1,2-diolate
  参考文献：
  名称：

  More Lipophilic Dialkyldiamine-Based Diazeniumdiolates:  Synthesis, Characterization, and Application in Preparing Thromboresistant Nitric Oxide Release Polymeric Coatings

  摘要：

  The synthesis, characterization, and biomedical application in preparing more thromboresistant polymeric coatings for a series of lipophilic dialkyldiamine-based diazeniumdiolates are described. Dialkylhexamethylenediamine diazeniumdiolates of the form RN[N(O)NO](-)-(CH2)(6)(NH2R)-R-divided by, where R = CH3, CH2CH3, (CH2)(2)CH3, (CH2)(3)CH3, (CH2)(4)CH3, (CH2)(5)CH3, and (CH2)(11)CH3, are prepared via reaction of the corresponding diamine with NO. The more lipophilic diazeniumdiolates [e.g., R = (CH2)(3)CH3] can be incorporated into hydrophobic polymeric films (e.g., plasticized PVC), and the resulting materials release NO for extended periods of time upon exposure to PBS buffer. The mechanism of NO release from these films is examined in detail. More stable initial NO release can be achieved by adding lipophilic anionic species (e.g., tetraphenylborate derivative) to the polymeric material to buffer the activity of protons within the organic phase. It is shown that the use of these new lipophilic NO-donors in polymers provides the ability to tailor NO release rates for a variety of medical applications. As an example, polymers doped with N,N'-dibutylhexamethylenediamine diazeniumdiolate and a tetraphenylborate derivative are employed as coatings for vascular grafts in sheep. The NO release grafts exhibited enhanced performance and had an average 95% thrombus-free surface area compared to 42% for the corresponding control grafts when examined after 21d of implantation.

  DOI：

  10.1021/jm030286t
• 作为产物：
  描述：

  己二酰氯 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 19.0h， 生成 N,N'-dipentyl-1,6-hexanediamine
  参考文献：
  名称：

  More Lipophilic Dialkyldiamine-Based Diazeniumdiolates:  Synthesis, Characterization, and Application in Preparing Thromboresistant Nitric Oxide Release Polymeric Coatings

  摘要：

  The synthesis, characterization, and biomedical application in preparing more thromboresistant polymeric coatings for a series of lipophilic dialkyldiamine-based diazeniumdiolates are described. Dialkylhexamethylenediamine diazeniumdiolates of the form RN[N(O)NO](-)-(CH2)(6)(NH2R)-R-divided by, where R = CH3, CH2CH3, (CH2)(2)CH3, (CH2)(3)CH3, (CH2)(4)CH3, (CH2)(5)CH3, and (CH2)(11)CH3, are prepared via reaction of the corresponding diamine with NO. The more lipophilic diazeniumdiolates [e.g., R = (CH2)(3)CH3] can be incorporated into hydrophobic polymeric films (e.g., plasticized PVC), and the resulting materials release NO for extended periods of time upon exposure to PBS buffer. The mechanism of NO release from these films is examined in detail. More stable initial NO release can be achieved by adding lipophilic anionic species (e.g., tetraphenylborate derivative) to the polymeric material to buffer the activity of protons within the organic phase. It is shown that the use of these new lipophilic NO-donors in polymers provides the ability to tailor NO release rates for a variety of medical applications. As an example, polymers doped with N,N'-dibutylhexamethylenediamine diazeniumdiolate and a tetraphenylborate derivative are employed as coatings for vascular grafts in sheep. The NO release grafts exhibited enhanced performance and had an average 95% thrombus-free surface area compared to 42% for the corresponding control grafts when examined after 21d of implantation.

  DOI：

  10.1021/jm030286t

文献信息

• Bis-diazeniumdiolates of Dialkyldiamines:  Enhanced Nitric Oxide Loading of Parent Diamines
  作者：Melissa M. Reynolds、Zhengrong Zhou、Bong K. Oh、Mark E. Meyerhoff

  DOI：10.1021/ol050541z

  日期：2005.7.1

  [reaction: see text] The synthesis and characterization of a series of symmetric bis-dialkyldiamine-based diazeniumdiolates, RN[N(O)NO(-)Na(+)](CH(2))(x)()N[N(O)NO(-)Na(+)]R', are reported. Preparation of corresponding intramolecular diazeniumdiolates of the form RN[N(O)NO](-)(CH(2))(x)()NH(2)(+)R' with alkyl groups > (CH(2))(4)CH(3) have been shown previously to lack stability. In contrast, sodium-stabilized

  [反应：请参阅文本]一系列对称的基于双二烷基二胺的二氮杂二烯二醇鎓盐RN [N（O）NO（-）Na（+）]（CH（2））（x）（）N [据报道，N（O）NO（-）Na（+）] R'。制备形式为RN [N（O）NO]（-）（CH（2））（x）（）NH（2）（+）R'的烷基>（CH（2））（ 4）CH（3）先前已显示出缺乏稳定性。相反，当将这些相同的二胺在碱性介质中与NO反应时，可以容易地形成这种亲脂性物质的钠稳定的双二氮烯二醇盐。相对于每摩尔原始二胺，所得化合物释放出4摩尔NO。这种方法能够合成比以前更多的亲脂性NO供体。
• Use of additive sites to control nitric oxide release from nitric oxide donors contained within polymers
  申请人：Meyerhoff E. Mark

  公开号：US20060008529A1

  公开（公告）日：2006-01-12

  A method for increasing, prolonging, and/or controlling the release rates of nitric oxide (NO) from polymeric materials containing NO adducts. Such NO-containing polymeric materials may find use in devices such as blood contacting devices, and biocompatible devices utilizing the same. The method and device utilizes anionic site additives, acidic site additives and/or acidic producing site additives in a polymer that contains NO-adducts to generate higher fluxes of NO to exceed NO threshold levels desirable to substantially prevent and/or minimize reactions such as platelet activation or adhesion.

  一种增加、延长和/或控制聚合物材料中含有NO加合物的释放速率的方法。这种含有NO的聚合物材料可以在血液接触设备等设备中找到用途，并且利用相同的生物相容性设备。该方法和设备利用阴离子位添加剂、酸性位添加剂和/或产生酸性位添加剂在含有NO加合物的聚合物中产生更高通量的NO，超过NO阈值水平，以实现大幅预防和/或最小化诸如血小板活化或粘附等反应。
• Process for preparation of disecondary diamines
  申请人：DU PONT

  公开号：US02334782A1

  公开（公告）日：1943-11-23
• Use of Additive Sites to Control Nitric Oxide Release from Nitric Oxide Donors Contained within Polymers
  申请人：Meyerhoff Mark E.

  公开号：US20110117164A1

  公开（公告）日：2011-05-19

  A method for increasing, prolonging, and/or controlling the release rates of nitric oxide (NO) from polymeric materials containing NO adducts. Such NO-containing polymeric materials may find use in devices such as blood contacting devices, and biocompatible devices utilizing the same. The method and device utilizes anionic site additives, acidic site additives and/or acidic producing site additives in a polymer that contains NO-adducts to generate higher fluxes of NO to exceed NO threshold levels desirable to substantially prevent and/or minimize reactions such as platelet activation or adhesion.
• US4291150A
  申请人：——

  公开号：US4291150A

  公开（公告）日：1981-09-22