1-chloro-3-(N-ethyl-N-phenylamino)propan-2-ol | 71176-56-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-chloro-3-(N-ethyl-N-phenylamino)propan-2-ol
• 英文别名: 1-chloro-3-(N-ethylanilino)propan-2-ol；1-(N-ethyl-anilino)-3-chloro-propan-2-ol；1-(N-Aethyl-anilino)-3-chlor-propan-2-ol；1-Chloro-3-(ethylphenylamino)-2-propanol
• CAS: 71176-56-2
• 化学式: C₁₁H₁₆ClNO
• 分子量: 213.707
• InChiKey: XRVZENCDEZEWAE-UHFFFAOYSA-N

物化性质

• 沸点：
  333.7±32.0 °C(Predicted)
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-chloro-3-(N-ethyl-N-phenylamino)propan-2-ol 在 potassium carbonate 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 60.0h， 生成 3-(N-ethyl-N-phenylamino)-1-(uracil-1-yl)propane-2-ol
  参考文献：
  名称：

  Synthesis, Src kinase inhibitory and anticancer activities of 1-substituted 3-(N-alkyl-N-phenylamino)propane-2-ols

  摘要：

  A series of 3-(N-alkyl-N-phenylamino)propan-2-ol derivatives were synthesized from epichlorohydrine in a multi-step strategy and were evaluated as Src kinase inhibitors. First, epoxy ring opening of epichlorohydrine was carried out in the presence of N-alkylanilines to yield 3-(N-alkyl-N-phenylamino)-1-chloro-propan-2-ol derivatives using Ca(OTf)(2) as catalyst based on our previous studies [1]. Second, ring closure was performed under basic conditions to afford N-epoxymethyl N-alkylaniline derivatives. Finally, the epoxide ring opening with four different secondary amines and three nucleobases afforded the final products, i.e., a series of beta-amino alcohols. All compounds were screened for their inhibitory activity against Src kinase and anticancer activity on human breast carcinoma cells, BT-20 cell line. Among all compounds, 3-N-methyl-N-phenylamino-1-(pyrrolidin-1-yl)propan-2-ol (13b) exhibited the highest inhibitory potency (IC50 = 66.1 mu M) against Src kinase. Structure-activity relationship studies suggested that the incorporation of bulky groups at position I and N-substitution with groups larger than methyl moiety, reduced the inhibitory potency of the compound significantly. Compounds 3-(N-ethyl-N-phenylamino-)-1-(4-methylpiperazin-1-yl)propan-2-ol (14c) and 3-(N-ethyl-N-phenylamino)-1-(thymine-1-yl)propan-2-ol (17) were found to inhibit the growth of breast carcinoma cells by approximately 45-49% at concentration of 50 mu M. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.biochi.2010.04.022
• 作为产物：
  描述：

  N-乙基苯胺 、 环氧氯丙烷 以 甲醇 、 水 为溶剂， 生成 1-chloro-3-(N-ethyl-N-phenylamino)propan-2-ol
  参考文献：
  名称：

  从环氧乙烷简单合成 β-乙酰氧基硫氰酸酯

  摘要：

  摘要描述了一种方便且简单的方法，该方法通过相应的环氧乙烷与硫氰酸根阴离子的区域选择性开环然后乙酰化来制备以前未知的 β-乙酰氧基硫氰酸盐。该方法的优点是反应时间更短、产物产率更高且易于处理。

  DOI：

  10.1080/00397911.2010.494817

文献信息

• Kuroki et al., Kogyo Kagaku zasshi / Journal of the Society of Chemical Industry, 1956, vol. 59, p. 626,629
  作者：Kuroki et al.

  DOI：——

  日期：——
• Syntheses proceeding from N-(oxiran-2-ylmethyl)-N-ethylaniline
  作者：E. G. Mesropyan、A. S. Galstyan、A. A. Avetisyan

  DOI：10.1134/s1070428010090058

  日期：2010.9

  The preparation of N-(oxiran-2-ylmethyl)-N-ethylaniline was developed. The compound was used in the synthesis of new N-derivatives of aromatic amines containing vicinal aminoalcohol moieties.
• Kitao et al., Bulletin of University of Osaka Prefecture, Series A: Engineering and Natural Sciences, 1959, vol. 7, p. 85,95
  作者：Kitao et al.

  DOI：——

  日期：——
• US3935182A
  申请人：——

  公开号：US3935182A

  公开（公告）日：1976-01-27
• US3945991A
  申请人：——

  公开号：US3945991A

  公开（公告）日：1976-03-23