(+/-)-N,N-dibenzyl-2-aminooctan-1-ol | 750592-68-8

• 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,N-dibenzyl-2-aminooctan-1-ol
• 英文别名: 2-(dibenzylamino)octan-1-ol
• CAS: 750592-68-8
• 化学式: C₂₂H₃₁NO
• 分子量: 325.494
• InChiKey: IKBKLEAVTASPMS-UHFFFAOYSA-N

物化性质

• 沸点：
  442.9±25.0 °C(Predicted)
• 密度：
  1.016±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  24.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  23.47
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (+/-)-N,N-dibenzyl-2-aminooctan-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 生成 (+/-)-N,N-dibenzyl-3-aminononan-2-ol
  参考文献：
  名称：

  4,5-Dialkylsubstituted 2-imino-1,3-thiazolidine derivatives as potent inducible nitric oxide synthase inhibitors

  摘要：

  In the course of our search for selective iNOS inhibitors, we have previously reported that 2-imino-1,3-oxazolidine derivatives (1) and 2-aminothiazole derivatives (2) are selective iNOS inhibitors. In order to find more potent iNOS inhibitors, we focused our efforts on the synthesis and evaluation of the inhibitory activity against iNOS and selectivity for iNOS both in vitro and in vivo of a series of 2-imino-1,3-thiazolidine derivatives (3), which are analogues of I and 2. Our results show that among the compounds synthesized (4R,5R)-5-ethyl-2-imino-4-methyl-1,3-thiazolidine [(4R,5R)-14a: ES-1537] exhibited potent inhibitory activity and selectivity for iNOS. In addition, ES-1537 had good pharmacokinetic profile in rats with BA value of 80%. It is therefore expected that ES-1537 may be therapeutically useful for the treatment of diseases related to excess production of NO. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.031
• 作为产物：
  描述：

  2-Dibenzylamino-octanoic acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以8.89 g的产率得到(+/-)-N,N-dibenzyl-2-aminooctan-1-ol
  参考文献：
  名称：

  4,5-Dialkylsubstituted 2-imino-1,3-thiazolidine derivatives as potent inducible nitric oxide synthase inhibitors

  摘要：

  In the course of our search for selective iNOS inhibitors, we have previously reported that 2-imino-1,3-oxazolidine derivatives (1) and 2-aminothiazole derivatives (2) are selective iNOS inhibitors. In order to find more potent iNOS inhibitors, we focused our efforts on the synthesis and evaluation of the inhibitory activity against iNOS and selectivity for iNOS both in vitro and in vivo of a series of 2-imino-1,3-thiazolidine derivatives (3), which are analogues of I and 2. Our results show that among the compounds synthesized (4R,5R)-5-ethyl-2-imino-4-methyl-1,3-thiazolidine [(4R,5R)-14a: ES-1537] exhibited potent inhibitory activity and selectivity for iNOS. In addition, ES-1537 had good pharmacokinetic profile in rats with BA value of 80%. It is therefore expected that ES-1537 may be therapeutically useful for the treatment of diseases related to excess production of NO. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.031

文献信息

• Ligand-Controlled Regiodivergent Cu-Catalyzed Aminoboration of Unactivated Terminal Alkenes
  作者：Ryosuke Sakae、Koji Hirano、Masahiro Miura

  DOI：10.1021/jacs.5b02775

  日期：2015.5.27

  A ligand-controlled regiodivergent Cu-catalyzed aminoboration of unactivated terminal alkenes with diboron reagents and hydroxylamines has been developed. The xantphos-ligated CuCl complex guides the boron and amino groups to the terminal and internal positions, respectively. On the other hand, the opposite regioisomers are selectively obtained under the N-heterocyclic carbene-based IPrCuBr catalysis

  已开发出一种配体控制的区域发散性铜催化未活化末端烯烃与二硼试剂和羟胺的氨基硼化反应。xantphos 连接的 CuCl 复合物将硼和氨基分别引导到末端和内部位置。另一方面，在基于 N-杂环卡宾的 IPrCuBr 催化下选择性地获得相反的区域异构体。这两种铜催化剂可以很容易地将简单而丰富的末端烯烃区域发散地转化为高价值的 β-硼烷基胺。