2-benzyloxy-N-benzylaniline | 39860-73-6

• 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: 2-benzyloxy-N-benzylaniline
• 英文别名: N-[(2-benzyloxyphenyl)methyl]aniline；N-(2-(benzyloxy)benzyl)aniline；ortho-N-Benzyloxybenzyl-anilin；N-[(2-phenylmethoxyphenyl)methyl]aniline
• CAS: 39860-73-6
• 化学式: C₂₀H₁₉NO
• 分子量: 289.377
• InChiKey: FAABPZDIUVSFGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-benzyloxy-N-benzylaniline 在 titanium(III) chloride 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以48%的产率得到2-[(苯基氨基)甲基]苯酚
  参考文献：
  名称：

  Talukdar, Sanjay; Banerji, Asoke, Journal of the Indian Chemical Society, 1997, vol. 74, # 11-12, p. 842 - 847

  摘要：

  DOI：
• 作为产物：
  描述：

  苯胺 在 sodium tetrahydroborate 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 反应 2.5h， 生成 2-benzyloxy-N-benzylaniline
  参考文献：
  名称：

  Identification of small molecule sphingomyelin synthase inhibitors

  摘要：

  Sphingomyelin synthase (SMS), which catalyzes ceramide as one of the substrates to produce sphingomyelin, is a critical factor in the sphingolipid biosynthesis pathway. Recent studies indicated that SMS could serve as a novel potential drug target for the treatment of various metabolic diseases such as insulin resistance and atherosclerosis. However, very few small-molecule inhibitors of SMS are known. In this study, we performed structure-based virtual screening in combination with chemical synthesis and bioassay and discovered a class of small-molecule SMS inhibitors. The most potent compound exhibited an IC50 value lower than 20 mu M in an in vitro enzymatic assay. To the best of our knowledge, this is the first time that small-molecule SMS inhibitors with potency close to the micromolar range are publicly revealed. The structure-activity relationship demonstrated by this class of compounds provides insights into the structural features that are essential for effective SMS inhibition. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.002

文献信息

• Direct Reductive Amination of Aldehydes and Ketones Using Phenylsilane:  Catalysis by Dibutyltin Dichloride
  作者：Richard Apodaca、Wei Xiao

  DOI：10.1021/ol015948s

  日期：2001.5.1

  A procedure for direct reductive amination of aldehydes and ketones was developed which uses phenylsilane as a stoichiometric reductant and dibutyltin dichloride as a catalyst. Suitable amines included anilines and dialkylamines but not monoalkylamines.

  开发了一种直接还原醛和酮的胺化方法，该方法使用苯基硅烷作为化学计量的还原剂，并使用二丁基二氯化锡作为催化剂。合适的胺包括苯胺和二烷基胺，但不包括单烷基胺。
• Identification of small molecule sphingomyelin synthase inhibitors
  作者：Xiaodong Deng、Fu Lin、Ya Zhang、Yan Li、Lu Zhou、Bin Lou、Yue Li、Jibin Dong、Tingbo Ding、Xiancheng Jiang、Renxiao Wang、Deyong Ye

  DOI：10.1016/j.ejmech.2013.12.002

  日期：2014.2

  Sphingomyelin synthase (SMS), which catalyzes ceramide as one of the substrates to produce sphingomyelin, is a critical factor in the sphingolipid biosynthesis pathway. Recent studies indicated that SMS could serve as a novel potential drug target for the treatment of various metabolic diseases such as insulin resistance and atherosclerosis. However, very few small-molecule inhibitors of SMS are known. In this study, we performed structure-based virtual screening in combination with chemical synthesis and bioassay and discovered a class of small-molecule SMS inhibitors. The most potent compound exhibited an IC50 value lower than 20 mu M in an in vitro enzymatic assay. To the best of our knowledge, this is the first time that small-molecule SMS inhibitors with potency close to the micromolar range are publicly revealed. The structure-activity relationship demonstrated by this class of compounds provides insights into the structural features that are essential for effective SMS inhibition. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Talukdar, Sanjay; Banerji, Asoke, Journal of the Indian Chemical Society, 1997, vol. 74, # 11-12, p. 842 - 847
  作者：Talukdar, Sanjay、Banerji, Asoke

  DOI：——

  日期：——