ω-(N,N-Dibenzylamino)-3-hydroxyacetophenone | 27382-20-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ω-(N,N-Dibenzylamino)-3-hydroxyacetophenone
• 英文别名: 2-[Bis(phenylmethyl)amino]-1-(3-hydroxyphenyl)ethanone；2-(dibenzylamino)-1-(3-hydroxyphenyl)ethanone
• CAS: 27382-20-3
• 化学式: C₂₂H₂₁NO₂
• 分子量: 331.414
• InChiKey: KWBSYHPGSOLJCN-UHFFFAOYSA-N

物化性质

• 沸点：
  505.6±45.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  碳酸氢铵 、 potassium cyanide 、 ω-(N,N-Dibenzylamino)-3-hydroxyacetophenone 在 Pearlman's catalist 、 氢气 作用下， 以 乙醇 、 水 、 甲醇 为溶剂， 20.0~70.0 ℃ 、344.75 kPa 条件下， 生成 5-(aminomethyl)-5-(3-hydroxyphenyl)imidazolidine-2,4-dione
  参考文献：
  名称：

  Discovery and SAR of hydantoin TACE inhibitors

  摘要：

  We disclose inhibitors of TNF-alpha converting enzyme (TACE) designed around a hydantoin zinc binding moiety. Crystal structures of inhibitors bound to TACE revealed monodentate coordination of the hydantoin to the zinc. SAR, X-ray, and modeling designs are described. To our knowledge, these are the first reported X-ray structures of TACE with a hydantoin zinc ligand. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.148
• 作为产物：
  描述：

  2-chloro-1-(3-hydroxy phenyl)ethan-1-one 、 二苄胺 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 ω-(N,N-Dibenzylamino)-3-hydroxyacetophenone
  参考文献：
  名称：

  Discovery and SAR of hydantoin TACE inhibitors

  摘要：

  We disclose inhibitors of TNF-alpha converting enzyme (TACE) designed around a hydantoin zinc binding moiety. Crystal structures of inhibitors bound to TACE revealed monodentate coordination of the hydantoin to the zinc. SAR, X-ray, and modeling designs are described. To our knowledge, these are the first reported X-ray structures of TACE with a hydantoin zinc ligand. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.148

文献信息

• Discovery and SAR of hydantoin TACE inhibitors
  作者：Wensheng Yu、Zhuyan Guo、Peter Orth、Vincent Madison、Lei Chen、Chaoyang Dai、Robert J. Feltz、Vinay M. Girijavallabhan、Seong Heon Kim、Joseph A. Kozlowski、Brian J. Lavey、Dansu Li、Daniel Lundell、Xiaoda Niu、John J. Piwinski、Janeta Popovici-Muller、Razia Rizvi、Kristin E. Rosner、Bandarpalle B. Shankar、Neng-Yang Shih、M. Arshad Siddiqui、Jing Sun、Ling Tong、Shelby Umland、Michael K.C. Wong、De-yi Yang、Guowei Zhou

  DOI：10.1016/j.bmcl.2010.01.148

  日期：2010.3

  We disclose inhibitors of TNF-alpha converting enzyme (TACE) designed around a hydantoin zinc binding moiety. Crystal structures of inhibitors bound to TACE revealed monodentate coordination of the hydantoin to the zinc. SAR, X-ray, and modeling designs are described. To our knowledge, these are the first reported X-ray structures of TACE with a hydantoin zinc ligand. (C) 2010 Elsevier Ltd. All rights reserved.