N-oxiranylmethyl-N-[3-phenyl-3-(4-trifluoromethylphenoxy)propyl]methylamine | 848072-60-6

• 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-oxiranylmethyl-N-[3-phenyl-3-(4-trifluoromethylphenoxy)propyl]methylamine
• 英文别名: methyl-oxiranylmethyl-[3-phenyl-3-[4-(trifluoromethyl)-phenoxy]-propyl]amine；N-methyl-N-(oxiran-2-ylmethyl)-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine
• CAS: 848072-60-6
• 化学式: C₂₀H₂₂F₃NO₂
• 分子量: 365.395
• InChiKey: RNEWHVGIIQSAAL-UHFFFAOYSA-N

物化性质

• 沸点：
  447.6±45.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  25
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-oxiranylmethyl-N-[3-phenyl-3-(4-trifluoromethylphenoxy)propyl]methylamine 、 1-(3-氯苯基)哌嗪 以 乙醇 为溶剂， 以57%的产率得到1-[N-methyl-N-(3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl)amino]-3-[4-(3-chlorophenyl)piperazino]propan-2-ol trihydrochloride
  参考文献：
  名称：

  Substituted propanolamines and alkylamines derived from fluoxetine as potent appetite suppressants☆

  摘要：

  A series of propanolamine and alkylamine analogues of fluoxetine (7-26, 28-31) were synthesized and assessed for their anorexigenic and antidepressant activities. Effect of various substituents at C-4 aryl position of fluoxetine has also been studied. Most of the propanolamine analogues (7-13, 16-26) displayed significant anorexigenic activity but interestingly they were devoid of antidepressant activity whereas anorexigenic as well as antidepressant activity was retained in the alkylamine series (28-31). Compounds 10 and 26 emerged as the most active compound and anorexigenic activity was better (83.67%) and 82.45%) compared to fluoxetine (81.25%). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.001
• 作为产物：
  描述：

  N-benzyl-N-methyl-3-phenyl-3-(4-trifluoromethylphenoxy)propanamine 在 potassium carbonate 、 氯甲酸甲酯 作用下， 以 乙醇 、 苯 为溶剂， 反应 34.0h， 生成 N-oxiranylmethyl-N-[3-phenyl-3-(4-trifluoromethylphenoxy)propyl]methylamine
  参考文献：
  名称：

  Substituted propanolamines and alkylamines derived from fluoxetine as potent appetite suppressants☆

  摘要：

  A series of propanolamine and alkylamine analogues of fluoxetine (7-26, 28-31) were synthesized and assessed for their anorexigenic and antidepressant activities. Effect of various substituents at C-4 aryl position of fluoxetine has also been studied. Most of the propanolamine analogues (7-13, 16-26) displayed significant anorexigenic activity but interestingly they were devoid of antidepressant activity whereas anorexigenic as well as antidepressant activity was retained in the alkylamine series (28-31). Compounds 10 and 26 emerged as the most active compound and anorexigenic activity was better (83.67%) and 82.45%) compared to fluoxetine (81.25%). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.001

文献信息

• Carbodithioic acid esters of fluoxetine, a novel class of dual-function spermicides
  作者：S.T.V.S. Kiran Kumar、Lalit Kumar、Vishnu L. Sharma、Ashish Jain、Rajeev K. Jain、Jagdamba P. Maikhuri、Manish Kumar、Praveen K. Shukla、Gopal Gupta

  DOI：10.1016/j.ejmech.2007.10.024

  日期：2008.10

  Carbodithioic acid esters of fluoxetine have been prepared by replacing the methylamino function in aminopropane chain with carbodithioic acid ester group and by adding various S-2-hydroxypropyl ester of dialkyl carbodithioic acid at 3-methylamino group. Some of these compounds showed spermicidal, antifungal and anti-Trichomonas activities. The study revealed that incorporation of carbodithioic acid residue directly into fluoxetine structure leads to compounds with better antifungal and anti-Trichomonas activities, and N-methyl-[3-phenyl-3-(4-trifluoromethylphenoxy)-propyl]carbodithioic acid S-(2-pyrrolidino-ethyl) ester (14) has shown better profile than both fluoxetine and nonoxynol-9. Further lead optimization may yield a potent dual-function spermicide. (C) 2007 Elsevier Masson SAS. All rights reserved.
• Substituted propanolamines and alkylamines derived from fluoxetine as potent appetite suppressants☆
  作者：Kalpana Bhandari、Shipra Srivastava、Girija Shanker、Chandishwar Nath

  DOI：10.1016/j.bmc.2004.12.001

  日期：2005.3.1

  A series of propanolamine and alkylamine analogues of fluoxetine (7-26, 28-31) were synthesized and assessed for their anorexigenic and antidepressant activities. Effect of various substituents at C-4 aryl position of fluoxetine has also been studied. Most of the propanolamine analogues (7-13, 16-26) displayed significant anorexigenic activity but interestingly they were devoid of antidepressant activity whereas anorexigenic as well as antidepressant activity was retained in the alkylamine series (28-31). Compounds 10 and 26 emerged as the most active compound and anorexigenic activity was better (83.67%) and 82.45%) compared to fluoxetine (81.25%). (C) 2004 Elsevier Ltd. All rights reserved.