(2S,4R)-6-bromo-2-methyl-2-propyl-3,4-dihydrochromen-4-ol | 1448783-84-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (2S,4R)-6-bromo-2-methyl-2-propyl-3,4-dihydrochromen-4-ol
• CAS: 1448783-84-3
• 化学式: C₁₃H₁₇BrO₂
• 分子量: 285.181
• InChiKey: JFLDMUDSJGQVIM-YPMHNXCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,4R)-6-bromo-2-methyl-2-propyl-3,4-dihydrochromen-4-ol 在 咪唑 、 Pd(1,1-bis(diphenylphosphino)ferrocene)₂Cl₂ 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Design and synthesis of hydroxyethylamine (HEA) BACE-1 inhibitors: Prime side chromane-containing inhibitors

  摘要：

  The structure structure activity relationship of the prime region of conformationally restricted hydroxyethylamine (HEA) BACE inhibitors is described. Variation of the P1' region provided selectivity over Cat-D with a series of 2,2-dioxo-isothiochromanes and optimization of the P2' substituent of chromane-HEA(s) with polar substituents provided improvements in the compound's in vitro permeability. Significant potency gains were observed with small aliphatic substituents such as methyl, n-propyl, and cyclopropyl when placed at the C-2 position of the chromane. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.006
• 作为产物：
  描述：

  2-羟基-5-溴苯乙酮 在 四氢吡咯 、 dimethyl sulfide borane 、 (S)-2-甲基-CBS-恶唑硼烷 作用下， 以 甲苯 、 乙腈 为溶剂， 生成 (2S,4R)-6-bromo-2-methyl-2-propyl-3,4-dihydrochromen-4-ol
  参考文献：
  名称：

  Design and synthesis of hydroxyethylamine (HEA) BACE-1 inhibitors: Prime side chromane-containing inhibitors

  摘要：

  The structure structure activity relationship of the prime region of conformationally restricted hydroxyethylamine (HEA) BACE inhibitors is described. Variation of the P1' region provided selectivity over Cat-D with a series of 2,2-dioxo-isothiochromanes and optimization of the P2' substituent of chromane-HEA(s) with polar substituents provided improvements in the compound's in vitro permeability. Significant potency gains were observed with small aliphatic substituents such as methyl, n-propyl, and cyclopropyl when placed at the C-2 position of the chromane. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.006

文献信息

• Design and synthesis of hydroxyethylamine (HEA) BACE-1 inhibitors: Prime side chromane-containing inhibitors
  作者：Raymond A. Ng、Minghua Sun、Simeon Bowers、Roy K. Hom、Gary D. Probst、Varghese John、Lawrence Y. Fang、Michel Maillard、Andrea Gailunas、Louis Brogley、R. Jeffrey Neitz、Jay S. Tung、Michael A. Pleiss、Andrei W. Konradi、Hing L. Sham、Michael S. Dappen、Marc Adler、Nanhua Yao、Wes Zmolek、David Nakamura、Kevin P. Quinn、John-Michael Sauer、Michael P. Bova、Lany Ruslim、Dean R. Artis、Ted A. Yednock

  DOI：10.1016/j.bmcl.2013.06.006

  日期：2013.8

  The structure structure activity relationship of the prime region of conformationally restricted hydroxyethylamine (HEA) BACE inhibitors is described. Variation of the P1' region provided selectivity over Cat-D with a series of 2,2-dioxo-isothiochromanes and optimization of the P2' substituent of chromane-HEA(s) with polar substituents provided improvements in the compound's in vitro permeability. Significant potency gains were observed with small aliphatic substituents such as methyl, n-propyl, and cyclopropyl when placed at the C-2 position of the chromane. (C) 2013 Elsevier Ltd. All rights reserved.