(S)-5-bromo-2-(3,6-dihydro-2H-pyran-3-yloxy)benzaldehyde | 1609694-52-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-5-bromo-2-(3,6-dihydro-2H-pyran-3-yloxy)benzaldehyde
• 英文别名: 5-bromo-2-[[(3S)-3,6-dihydro-2H-pyran-3-yl]oxy]benzaldehyde
• CAS: 1609694-52-1
• 化学式: C₁₂H₁₁BrO₃
• 分子量: 283.122
• InChiKey: PXFPVWSGNIUKMV-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-5-bromo-2-(3,6-dihydro-2H-pyran-3-yloxy)benzaldehyde 在 三乙基硅烷 、 伯吉斯试剂 、 羟基甲苯磺酰碘苯 、 盐酸羟胺 、 氢气 、 sodium acetate trihydrate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 甲烷磺酸 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 9.53h， 生成 (4aS,10aS)-7-bromo-5-methylene-1,3,4,4a,5,10a-hexahydropyrano[3,4-b]chromene
  参考文献：
  名称：

  Synthesis, characterization, and PK/PD studies of a series of spirocyclic pyranochromene BACE1 inhibitors

  摘要：

  The development of 1,3,4,4a,5,10a-hexahydropyrano[3,4-b]chromene analogs as BACE1 inhibitors is described. Introduction of the spirocyclic pyranochromene scaffold yielded several advantages over previous generation cores, including increased potency, reduced efflux, and reduced CYP2D6 inhibition. Compound 13 ( BACE1 IC50 = 110 nM) demonstrated a reduction in CSF Ab in wild type rats after a single dose. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.012
• 作为产物：
  描述：

  (S)-3,6-二氢-2H-吡喃-3-醇 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.5h， 生成 (S)-5-bromo-2-(3,6-dihydro-2H-pyran-3-yloxy)benzaldehyde
  参考文献：
  名称：

  Synthesis, characterization, and PK/PD studies of a series of spirocyclic pyranochromene BACE1 inhibitors

  摘要：

  The development of 1,3,4,4a,5,10a-hexahydropyrano[3,4-b]chromene analogs as BACE1 inhibitors is described. Introduction of the spirocyclic pyranochromene scaffold yielded several advantages over previous generation cores, including increased potency, reduced efflux, and reduced CYP2D6 inhibition. Compound 13 ( BACE1 IC50 = 110 nM) demonstrated a reduction in CSF Ab in wild type rats after a single dose. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.012

文献信息

• Synthesis, characterization, and PK/PD studies of a series of spirocyclic pyranochromene BACE1 inhibitors
  作者：Matthew Volgraf、Lina Chan、Malcolm P. Huestis、Hans E. Purkey、Michael Burkard、Mary Geck Do、Julie Harris、Kevin W. Hunt、Xingrong Liu、Joseph P. Lyssikatos、Sumeet Rana、Allen A. Thomas、Guy P.A. Vigers、Michael Siu

  DOI：10.1016/j.bmcl.2014.04.012

  日期：2014.6

  The development of 1,3,4,4a,5,10a-hexahydropyrano[3,4-b]chromene analogs as BACE1 inhibitors is described. Introduction of the spirocyclic pyranochromene scaffold yielded several advantages over previous generation cores, including increased potency, reduced efflux, and reduced CYP2D6 inhibition. Compound 13 ( BACE1 IC50 = 110 nM) demonstrated a reduction in CSF Ab in wild type rats after a single dose. (C) 2014 Elsevier Ltd. All rights reserved.