2-(2-bromo-5-methoxyphenyl)ethyl chloride | 75534-19-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2-bromo-5-methoxyphenyl)ethyl chloride
• 英文别名: 2-bromo-5-methoxyphenethyl chloride；1-bromo-2-(2-chloroethyl)-4-methoxybenzene
• CAS: 75534-19-9
• 化学式: C₉H₁₀BrClO
• 分子量: 249.535
• InChiKey: MPGNNQUSFWATGI-UHFFFAOYSA-N

物化性质

• 沸点：
  90-95 °C(Press: 0.01 Torr)
• 密度：
  1.435±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2-bromo-5-methoxyphenyl)ethyl chloride 在 草酰氯 、 camphor-10-sulfonic acid 、 叔丁基锂 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 4-oxo-7-methoxy-1,2,3,4,9,10-hexahydrophenanthrene
  参考文献：
  名称：

  Six-membered-ring annulation via a conjugate addition-alkylation sequence using functionalized aryllithium reagents and vinyl sulfones

  摘要：

  DOI：

  10.1021/jo00314a026
• 作为产物：
  描述：

  2-(2-溴-5-甲氧基苯基)乙醇 在 四氯化碳 、 三苯基膦 作用下， 反应 14.0h， 以85%的产率得到2-(2-bromo-5-methoxyphenyl)ethyl chloride
  参考文献：
  名称：

  Discovery and stereoselective synthesis of the novel isochroman neurokinin-1 receptor antagonist ‘CJ-17,493’

  摘要：

  A novel central nervous system (CNS) selective neurokinin-1 (NK1) receptor antagonist, (2S, 3S)-3-[(1R)-6-methoxy- 1-methyl-1-trifluoromethylisochroman-7-yl]-methylamino-2-phenylpiperidine 'CJ-17,493'( compound (+)-1), was synthesized stereoselectively using a kinetic resolution by lipase-PS as a key step. Compound (+)-1 displayed high and selective affinity (K-i = 0.2 nM) for the human NK1 receptor in IM-9 cells, potent activity in the [Sar(9), Met(O-2)(11)] SP-induced gerbil tapping model (ED50 = 0.04 mg/kg, sc) and in the ferret cisplatin (10 mg/kg, ip)-induced anti-emetic activity model (vomiting: ED90 = 0.07 mg/kg, sc), all levels of activity comparable with those of CP-122,721. In addition, compound (+)-1 exhibited linear pharmacokinetics rather than the super dose-proportionality of CP-122,721 and this result provides a potential solution for the clinical issue observed with CP-122,721. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.047

文献信息

• Bioorg. Med. Chem. 2008, 16, 7193-7205
  作者：

  DOI：——

  日期：——
• PONTON J.; HELQUIST P.; CONRAD P. C.; FUCHS P. L., J. ORG. CHEM., 1981, 46, NO 1, 118-122
  作者：PONTON J.、 HELQUIST P.、 CONRAD P. C.、 FUCHS P. L.

  DOI：——

  日期：——
• Discovery and stereoselective synthesis of the novel isochroman neurokinin-1 receptor antagonist ‘CJ-17,493’
  作者：Yuji Shishido、Hiroaki Wakabayashi、Hiroki Koike、Naomi Ueno、Seiji Nukui、Tatsuya Yamagishi、Yoshinori Murata、Fumiharu Naganeo、Mayumi Mizutani、Kaoru Shimada、Yoshiko Fujiwara、Ayano Sakakibara、Osamu Suga、Rinko Kusano、Satoko Ueda、Yoshihito Kanai、Megumi Tsuchiya、Kunio Satake

  DOI：10.1016/j.bmc.2008.06.047

  日期：2008.8

  A novel central nervous system (CNS) selective neurokinin-1 (NK1) receptor antagonist, (2S, 3S)-3-[(1R)-6-methoxy- 1-methyl-1-trifluoromethylisochroman-7-yl]-methylamino-2-phenylpiperidine 'CJ-17,493'( compound (+)-1), was synthesized stereoselectively using a kinetic resolution by lipase-PS as a key step. Compound (+)-1 displayed high and selective affinity (K-i = 0.2 nM) for the human NK1 receptor in IM-9 cells, potent activity in the [Sar(9), Met(O-2)(11)] SP-induced gerbil tapping model (ED50 = 0.04 mg/kg, sc) and in the ferret cisplatin (10 mg/kg, ip)-induced anti-emetic activity model (vomiting: ED90 = 0.07 mg/kg, sc), all levels of activity comparable with those of CP-122,721. In addition, compound (+)-1 exhibited linear pharmacokinetics rather than the super dose-proportionality of CP-122,721 and this result provides a potential solution for the clinical issue observed with CP-122,721. (C) 2008 Elsevier Ltd. All rights reserved.
• Six-membered-ring annulation via a conjugate addition-alkylation sequence using functionalized aryllithium reagents and vinyl sulfones
  作者：John Ponton、Paul Helquist、Preston C. Conrad、Philip L. Fuchs

  DOI：10.1021/jo00314a026

  日期：1981.1