1,3-bis(6-hydroxyhex-1-yl)urea | 100799-04-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: 1,3-bis(6-hydroxyhex-1-yl)urea
• 英文别名: N,N'-bis(6-hydroxyhexyl)urea；N,N'-bis-(6-hydroxy-hexyl)-urea；N,N'-Bis-(6-hydroxy-hexyl)-harnstoff；1,3-Bis(6-hydroxyhexyl)urea；1,3-bis(6-hydroxyhexyl)urea
• CAS: 100799-04-0
• 化学式: C₁₃H₂₈N₂O₃
• 分子量: 260.377
• InChiKey: IPIFRETURHRYKL-UHFFFAOYSA-N

物化性质

• 熔点：
  115-117 °C
• 沸点：
  486.4±30.0 °C(Predicted)
• 密度：
  1.029±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  81.6
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-bis(6-hydroxyhex-1-yl)urea 在 Jones reagent 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以72%的产率得到1,3-二(5-羧基戊基)脲
  参考文献：
  名称：

  Novel symmetrical ureas as modulators of protein arginine methyl transferases

  摘要：

  Methylation of histone arginine residues is an epigenetic mark related to gene expression that is implicated in a variety of biological processes and can be reversed by small-molecule modulators of protein arginine methyltransferases (PRMTs). A series of symmetrical ureas, designed as analogues of the known PRMT1 inhibitor AMI-1 have been synthesized using Pd-catalyzed Ar-N amide bond formation processes or carbonylation reactions as key steps. Their inhibitory profile has been characterized. The enzymatic assays showed a weak effect on PRMT1 and PRMT5 activity for most of the compounds. The acyclic urea that exhibited the strongest effect on the inhibition of the PRMT1 activity also showed the greatest effect on the expression of some androgen receptor target genes (TMPRSS2 and FKBP5), which may be related with its enzymatic activity. Surprisingly, AMI-1 behaved as an activator of PRMT5 activity, a result not reported so far. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.017
• 作为产物：
  描述：

  N,N'-bis-(6-hydroxy-hexyl)-thiourea 在 sodium hydroxide 、 双氧水 作用下， 生成 1,3-bis(6-hydroxyhex-1-yl)urea
  参考文献：
  名称：

  氨基醇与二硫化碳的反应

  摘要：

  在与二硫化碳缩合时，在氨基和羟基之间具有五个或更多亚甲基单元的 ω-氨基醇可得到良好的 1,3-二-(ω-羟烷基)硫脲。这些对称二取代的硫脲氧化得到相应的 1,3-二-(ω-羟基烷基)脲。

  DOI：

  10.1139/v58-018

文献信息

• Pd-catalysed oxidative carbonylation of amino alcohols to N,N′-bis(hydroxyalkyl)ureas under mild conditions using molecular oxygen as the oxidant
  作者：Potenzo Giannoccaro、Carla Ferragina、Michele Gargano、Eugenio Quaranta

  DOI：10.1016/j.apcata.2009.12.022

  日期：2010.2

  synthesis of symmetrical N,N′-bis(hydroxyalkyl)ureas, OC[NH-(CH2)x-OH]2 (x = 3–6), by oxidative carbonylation of α,ω-amino alcohols [3-aminopropanol (3-AP), 4-aminobutanol (4-AB), 5-aminopentanol (5-APe), 6-aminohexanol (6-AH)] with CO/O2 mixtures (O2 = 5 mol%) in the presence of Pd(II)/ligand/NEt3·HI catalytic systems. The catalytic process takes place under very mild conditions (p(CO/O2) = 0.1 MPa; 303–333 K)

  一个非常简单的方法已发展为对称的选择性合成N，N- ' -双（羟基烷基）脲，OC [NH-（CH 2）X -OH] 2（X  = 3-6），由α的氧化羰基化，ω-氨基醇[3-氨基丙醇（3-AP），4-氨基丁醇（4-AB），5-氨基戊醇（5-APe），6-氨基己醇（6-AH）]与CO / O 2混合物（O 在Pd（II）/配体/ NEt 3 ·HI催化体系的存在下为2 = 5 mol％。催化过程在非常温和的条件下（p（CO / O 2）= 0.1 MPa; 303–333 K）。可以通过非常简单直接的方法以高收率分离目标产物。催化系统可以轻松回收并循环使用多次。 还研究了一些反应参数（辅助配体和碘化物助催化剂的性质，I / Pd摩尔比等）对催化活性的影响，并充分阐明了催化过程的主要机理。
• Poly(urea ester): A family of biodegradable polymers with high melting temperatures
  作者：Donglin Tang、Zijian Chen、Felipe Correa-Netto、Christopher W. Macosko、Marc A. Hillmyer、Guangzhao Zhang

  DOI：10.1002/pola.28355

  日期：2016.12.15

  Poly(urea ester)s are a class of polymers developed to bridge the gap between aliphatic and aromatic polyesters in which high melting temperature and biodegradability are in a contradiction. These new class of biodegradable polymers melt at higher temperature, and they can be simply prepared by condensation of urea, amino alcohols and dimethyl esters.

  聚脲酯是一类聚合物，旨在弥合脂族和芳族聚酯之间的间隙，在这些间隙中，高熔融温度和生物降解性相互矛盾。这些新型的可生物降解的聚合物在较高的温度下熔融，可以通过缩合尿素，氨基醇和二甲基酯来简单地制备它们。
• REACTION OF AMINO ALCOHOLS WITH CARBON DISULPHIDE
  作者：A. F. McKay、M. Skulski、D. L. Garmaise

  DOI：10.1139/v58-018

  日期：1958.1.1

  ω-Amino alcohols possessing five or more methylene units between the amino and hydroxyl groups on condensation with carbon disulphide gave good yields of 1,3-di-(ω-hydroxyalkyl) thioureas. These symmetrically disubstituted thioureas on oxidation gave the corresponding 1,3-di-(ω-hydroxyalkyl) ureas.

  在与二硫化碳缩合时，在氨基和羟基之间具有五个或更多亚甲基单元的 ω-氨基醇可得到良好的 1,3-二-(ω-羟烷基)硫脲。这些对称二取代的硫脲氧化得到相应的 1,3-二-(ω-羟基烷基)脲。
• Novel symmetrical ureas as modulators of protein arginine methyl transferases
  作者：Noelia Fontán、Patricia García-Domínguez、Rosana Álvarez、Ángel R. de Lera

  DOI：10.1016/j.bmc.2013.01.017

  日期：2013.4

  Methylation of histone arginine residues is an epigenetic mark related to gene expression that is implicated in a variety of biological processes and can be reversed by small-molecule modulators of protein arginine methyltransferases (PRMTs). A series of symmetrical ureas, designed as analogues of the known PRMT1 inhibitor AMI-1 have been synthesized using Pd-catalyzed Ar-N amide bond formation processes or carbonylation reactions as key steps. Their inhibitory profile has been characterized. The enzymatic assays showed a weak effect on PRMT1 and PRMT5 activity for most of the compounds. The acyclic urea that exhibited the strongest effect on the inhibition of the PRMT1 activity also showed the greatest effect on the expression of some androgen receptor target genes (TMPRSS2 and FKBP5), which may be related with its enzymatic activity. Surprisingly, AMI-1 behaved as an activator of PRMT5 activity, a result not reported so far. (C) 2013 Elsevier Ltd. All rights reserved.