2,2′-iminobis-1,3-propanediol | 78531-52-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,2′-iminobis-1,3-propanediol
• 英文别名: bis(1,3-dihydroxy-isopropyl)amine；bis(1,3-dihydroxy-2-propyl)amine；bis(1,3-dihydroxyprop-2-yl)amine；bis(1,3-dihydroxy-prop-2-yl)amine；2,2'-Iminobis-1,3-propanediol；2-(1,3-dihydroxypropan-2-ylamino)propane-1,3-diol
• CAS: 78531-52-9
• 化学式: C₆H₁₅NO₄
• 分子量: 165.189
• InChiKey: UDAOBXRAGBHTNS-UHFFFAOYSA-N

物化性质

• 沸点：
  411.3±40.0 °C(Predicted)
• 密度：
  1.298±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2′-iminobis-1,3-propanediol 在 sodium hydroxide 、 sodium azide 、 四丁基硫酸氢铵 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(2'-azidoethyl)-bis[1,3-di-(tert-butyloxycarbonylethoxy)-isopropyl]amine
  参考文献：
  名称：

  Bis(1,3-dihydroxy-isopropyl)amine (BDI) as an AB4 dendritic building block: rapid synthesis of a second generation dendrimer

  摘要：

  Bis(1,3-dihydroxy-isopropyl)amine (BDI) 1, a symmetrical AB(4) dendritic building block, is developed into two diamine linkers in which the nitrogen is more nucleophilic. The four primary alcohols in BDI undergo Michael reactions with t-butyl acrylate. Branch cells of this rare multiplicity allow the rapid construction of a second generation dendrimer 5 with 48 protected peripheral primary alcohol groups. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00487-1
• 作为产物：
  描述：

  1,3-dihydroxyacetone dimer 在 sodium cyanoborohydride 、 氯化铵 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以85%的产率得到2,2′-iminobis-1,3-propanediol
  参考文献：
  名称：

  Bis(1,3-dihydroxy-prop-2-yl) amine and derivatives thereof in the manufacture of polymers

  摘要：

  双-(1,3-二羟基丙-2-基)胺的衍生物被披露，以及在聚合物制备中使用这些衍生物和双(1,3-二羟基丙-2-基)胺本身，特别是在树枝状聚合物的制备中。其中一些衍生物可能用作非离子表面活性剂。

  公开号：

  US06916948B2

文献信息

• An Acyclic Trialkylamine Virtually Planar at Nitrogen. Some Chemical Consequences of Nitrogen Planarity
  作者：Yuanping Jie、Peter Livant、Hui Li、Minmin Yang、Wei Zhu、Vince Cammarata、Philip Almond、Tyler Sullens、Yu Qin、Eric Bakker

  DOI：10.1021/jo100628v

  日期：2010.7.2

  consistent with the inductive effect of the 1,3-dihydroxy-2-propyl groups attached to nitrogen. It is also observed that the electrochemical oxidation of 9 is reversible on the CV time scale. The 15N NMR chemical shift of the essentially planar nitrogen atom of 9 is discussed.

  极度拥挤的胺三（1,3-二羟基-2-丙基）胺9的合成，总产率为47- 51％。9的氮原子实际上是平面的；它在三个碳原子定义的平面之外为0.082Å。对于三异丙胺，相应的面外测量值为0.282Å，而对于 未充填的三烷基胺为0.4Å。尽管存在空间拥塞，但9的N-C键还是很短的。9（即9 H +）的共轭酸非常强：p K a = 3.08（cf. Et 3 NH + p K a= 10.7）。与合适的模型化合物的比较表明，9的碱性比ca预测的要弱。1.5 p K a单位。结构9 ħ +氯-通过X射线晶体学确定。在此，氮也相对于普通铵阳离子严重展平。在9 ħ +氯- ，对氮的质子9点ħ +形成三个分子内氢键成羟基基团，即，所谓的三叉氢键。NH···O的长度为9 H +比可比的三叉氢键短一些 循环伏安法（CV）在9上发现E 1/2 ox为0.88 V，这与连接到氮上的1,3-二羟基-2-丙基的感应效应
• Bis(1,3-dinitratoprop-2-yl) Nitramine, a New Sensitive Explosive Combining a Nitrate Ester with a Nitramine
  作者：Thomas M. Klapötke、Burkhard Krumm、F. Xaver Steemann、Klaus-Daniel Umland

  DOI：10.1002/zaac.201000229

  日期：2010.11

  Abstract. Nitrofunctionalizedcompoundscomprisealargesubstanceclassandarethemostpopularexplosivematerials.Recentresearchfurnishedasolidenergeticnitrateesterofpotentialinterest.Thiswork Introduction Eversincethediscoveryofnitroglycerine(1 inScheme1)by Sobrero in1846[1],chemistshaveinvestigatednitratedandnitrofunctionalizedcompoundsfortheuseasenergeticsubstances.Theseendeavorsfurnishede.g.pentaerythr

  摘要。Nitrofunctionalizedcompoundscomprisealargesubstanceclassandarethemostpopularexplosivematerials.Recentresearchfurnishedasolidenergeticnitrateesterofpotentialinterest.Thiswork介绍Eversincethediscoveryofnitroglycerine（1 inScheme1）由SOBRERO in1846 [1]，chemistshaveinvestigatednitratedandnitrofunctionalizedcompoundsfortheuseasenergeticsubstances.Theseendeavorsfurnishede.g.pentaerythritolte-tranitrate（PETN，2
• Process for production of serinol and its bis-adduct
  申请人：Penn A Kem LLC

  公开号：US08653306B1

  公开（公告）日：2014-02-18

  An improved method for the production of 2-amino-1,3-propanediol (serinol) and its bis-adduct, 2,2′-iminobis-1,3-propanediol, from dihydroxyacetone and ammonia in the presence of a hydrogenation catalyst such as Raney nickel, followed by separation using an acidic ion-exchange resin.

  一种改进的方法，用氢化催化剂如Raney镍，在存在氨的情况下从双羟乙酮生产2-氨基-1,3-丙二醇（丝氨醇）及其双加合物2,2'-亚胺基双（1,3-丙二醇），随后使用酸性离子交换树脂进行分离。
• Synthesis of bis(1,3-dihydroxy-isopropyl)amine by reductive amination of dihydroxyacetone: Open chain equivalent of DMDP and a potential AB4 dendritic monomer
  作者：David A. Scott、Thomas M. Krülle、Malcolm Finn、Robert J. Nash、Ana L. Winters、Naoki Asano、Terry D. Butters、George W.J. Fleet

  DOI：10.1016/s0040-4039(99)01611-1

  日期：1999.10

  Reductive amination of dihydroxyacetone by ammonium salts with sodium cyanoborohydride gives bis(1,3-dihydroxy-isopropyl)amine [BDI] in good yield and high purity. BDI and its diacetonide are hindered nucleophiles but may be further reductively alkylated to form N-alkyl derivatives. BDI is an open chain equivalent of DMDP [2,5-dideoxy-2,5-imino-D-mannitol] but neither BDI nor its N-alkyl derivatives show inhibition of any glycosidase or transferase assayed. BDI may provide an example of an AB, dendritic monomer, (C) 1999 Elsevier Science Ltd. Ail rights reserved.
• HYDROXYL IONS AS UNIQUE THERAPEUTIC AGENTS AND COMPOUNDS THAT MODULATE THESE IONS, COMPOSITIONS EMPLOYING THESE AGENTS, THERAPEUTIC METHODS FOR USING SUCH AGENTS AND PROCESSES FOR PREPARING THEM
  申请人：FHJ SCIENTIFIC, INC.

  公开号：EP0725636A1

  公开（公告）日：1996-08-14