4-(allyloxy)aniline hydrochloride | 88271-75-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(allyloxy)aniline hydrochloride
• 英文别名: p-allyloxyaniline hydrochloride；4-allyloxy-aniline; hydrochloride；4-Allyloxy-anilin; Hydrochlorid；4-allyloxyaniline hydrochloride；4-prop-2-enoxyaniline;hydrochloride
• CAS: 88271-75-4
• 化学式: C₉H₁₁NO*ClH
• 分子量: 185.653
• InChiKey: OFPNXNRNUPFBAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  35.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(allyloxy)aniline hydrochloride 在 sodium dithionite 、 三乙胺 、 sodium nitrite 作用下， 以 乙醚 、 水 、 甲苯 为溶剂， 反应 2.75h， 生成 1-(4-chlorobenzyl)-1-<4-(allyloxy)phenyl>hydrazine
  参考文献：
  名称：

  Substituted thiopyrano[2,3,4-c,d]indoles as potent, selective, and orally active inhibitors of 5-lipoxygenase. Synthesis and biological evaluation of L-691,816

  摘要：

  Thiopyrano[2,3,4-c,d]indoles are a new class of 5-lipoxygenase (5-LO) inhibitors. SAR studies have demonstrated that the thiopyran ring, the 5-phenylpyridine substituent, and an acidic functional group on a four-carbon C-2 side chain are all required for optimal inhibitor potency. In contrast, the indolic nitrogen may be substituted with a variety of lipophilic groups. As a result of the SAR investigation, 44 (L-691,816; 5-[3-[1-(4-chlorobenzyl)-4-methyl-6-[(5-phenylpyridin-2-yl)methoxy]-4,5-dihydro-1H-thiopyrano[2,3,4-c,d]indol-2-yl]-2,2-dimethylpropyl]-1H-tetrazole) has been identified as a potent inhibitor of the 5-LO reaction both in vitro and in a range of in vivo models. Compound 44 inhibits 5-HPETE production by both rat and human 5-LO and LTB4 synthesis in human PMN leukocytes (IC50s 16,75, and 10 nM, respectively). The mechanism of inhibition of 5-LO activity by compound 44 appears to involve the formation of a reversible deadend complex with the enzyme and does not involve reduction of the nonheme iron of 5-LO. Compound 44 is highly selective for 5-LO when compared to the inhibition of human FLAP, porcine 12-LO, and also ram seminal vesicle cyclooxygenase. In addition, 44 is orally active in a rat pleurisy model (inhibition of LTB4, ED50 = 1.9 mg/kg; 8 h pretreatment) as well as in the hyperreactive rat model of antigen-induced dyspnea (ED50 = 0.1 mg/kg;2-h pretreatment). Excellent functional activity was also observed in both the conscious allergic monkey and sheep models of asthma. In the latter case, the functional activity observed correlated with the inhibition of urinary LTE4 excretion.

  DOI：

  10.1021/jm00071a008
• 作为产物：
  描述：

  对乙酰氨基酚 在 盐酸 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 50.0h， 生成 4-(allyloxy)aniline hydrochloride
  参考文献：
  名称：

  Comparative structure-activity relationships of antifolate triazines inhibiting murine tumor cells sensitive and resistant to methotrexate

  摘要：

  The inhibitory effect of 108 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-(substituted-phenyl)-s-triazines on murine L5178Y tumor cells, resistant and sensitive to methotrexate (MTX), has been studied. From the pI50 values, quantitative structure-activity relationships have been formulated which show that the lipophilic triazines are much more inhibitory against resistant cells than methotrexate or hydrophilic triazines. The results are compared with the behavior of other antifolate drugs that have been used in chemotherapy, as well as with eight antitumor drugs that are not antifolates. The acquired resistance of these cells toward hydrophilic antifolates may be attributed to the combined effect of an impaired active-transport system, a change in the conformation of dihydrofolate reductase in the resistant cells, and an amplified production of dihydrofolate reductase in the resistant cells.

  DOI：

  10.1021/jm00369a019

文献信息

• Self-immobilized catalysts for ethylene polymerization based on various phenoxyimine titanium halide complexes
  作者：N. I. Ivancheva、D. V. Sanieva、S. P. Fedorov、I. V. Oleinik、I. I. Oleinik、G. A. Tolstikov、S. S. Ivanchev

  DOI：10.1007/s11172-012-0116-4

  日期：2012.4

  The kinetic features of ethylene polymerization on ten methylalumoxane-activated self-immobilized bis(phenoxyimine) complexes of titanium chloride of various structure containing oxyallyl functional groups were studied. The catalytic activity of the systems was determined in the temperature range 20–60 °C under ethylene pressure 0.4 MPa. The positions and structures of the oxyallyl group and substituents

  研究了乙烯在十种甲基铝氧烷活化的自固定化双(苯氧基亚胺)配合物上的乙烯聚合动力学特征，该络合物具有各种结构的含氧烯丙基官能团。该系统的催化活性在 20-60°C 的温度范围内和 0.4 MPa 的乙烯压力下测定。配合物的氧烯丙基和苯氧基中的取代基的位置和结构显着改变了基于这些配合物的催化体系的活性、催化剂在聚合物上的自固定速率以及分子量和分子量所得聚乙烯的分布。
• Thiopyrano (2,3,4-c,d) indoles as inhibitors of leukotriene biosynthesis
  申请人：MERCK FROSST CANADA INC.

  公开号：EP0518426A1

  公开（公告）日：1992-12-16

  Compounds having the formula I: are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, psoriasis, uveitis and allograft rejection and in preventing the formation of atherosclerotic plaques.

  具有式 I 的化合物： 是白三烯生物合成的抑制剂。这些化合物可用作抗哮喘、抗过敏、抗炎和细胞保护剂。它们还可用于治疗心绞痛、脑痉挛、肾小球肾炎、肝炎、内毒素血症、银屑病、葡萄膜炎和异体移植排斥反应，以及预防动脉粥样硬化斑块的形成。
• Design of postmetallocene catalytic systems of arylimine type for olefin polymerization: XIV. Synthesis of (N-Allyloxyaryl)salicylaldimine ligands and their complexes with titanium(IV) dichloride
  作者：I. I. Oleinik、I. V. Oleinik、S. S. Ivanchev、G. A. Tolstikov

  DOI：10.1134/s1070428012080076

  日期：2012.8

  By reaction of salicylaldehydes with bulky substituents in the positions 3 and 5 with o-, m-, and p-allyloxyaniline hydrochlorides in the presence of triethylamine a series of the corresponding (N-aryl)-salicylaldimines was obtained, which with TiCl2(OPr-i)(2) afforded complexes of titanium(IV) dichloride L2TiCl2.
• Specific features of ethylene polymerization on self-immobilizing catalytic systems based on titanium bis(phenoxy imine) complexes
  作者：N. I. Ivancheva、V. K. Badaev、E. V. Sviridova、D. A. Nikolaev、I. V. Oleinik、S. S. Ivanchev

  DOI：10.1134/s1070427211010204

  日期：2011.1

  The kinetics of ethylene polymerization on six methylalumoxane-activated self-immobilizing bis(phenoxy imine) complexes of titanium chloride with allyloxy groups in the m- and p-positions of the N-phenyl ring and with various substituents in the salicylaldehyde fragment was studied. The activity of the complexes in the temperature range 20-60A degrees C and ethylene pressure of 0.4 MPa was evaluated.
• Multicentered self-immobilized ethylene polymerization catalysts based on functionalized titanium halide salicylaldiminate complexes for the synthesis of ultra-high-molecular-weight polyethylene
  作者：N. I. Ivancheva、S. Ya. Khaikin、E. V. Sviridova、S. P. Fedorov、D. V. Sanieva、O. V. Molev、I. V. Oleinik、S. S. Ivanchev

  DOI：10.1134/s1070427212090170

  日期：2012.9

  Specific features of ethylene polymerization using a new group of catalytic systems based on ten methylalumoxane-activated titanium halide salicylaldiminato complexes functionalized with omega-vinylalkoxy groups and containing tert-butyl substituents in the phenoxide moiety were studied. The catalytic activity of the new group of activated complexes is strongly affected by the position of the omega-vinylalkoxy functional group and by the number and position of substituents in the phenoxide moiety. These factors determine the ratio of the homogeneous and heterogeneous steps of the polymerization as a result of the catalyst self-immobilization onto the polymer formed, and also the molecular characteristics of the polymer obtained at 20, 40, and 60 degrees C and ethylene pressure of 0.4 MPa. The possibility and conditions of preparing ultra-high-molecular-weight polyethylene with improved morphology were revealed.