α-bromo-4'-isobutoxyacetophenone | 53704-76-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-bromo-4'-isobutoxyacetophenone
• 英文别名: 2-bromo-4'-(2-methylpropyloxy)acetophenone；2-Bromo-1-[4-(2-methylpropoxy)phenyl]ethanone
• CAS: 53704-76-0
• 化学式: C₁₂H₁₅BrO₂
• 分子量: 271.154
• InChiKey: GKPUHWKFWDMFIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  342.2±17.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  α-bromo-4'-isobutoxyacetophenone 在 四丁基氟化铵 、 sodium ethanolate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 为溶剂， 反应 21.0h， 生成 3-fluoro-4-(2-fluorobenzyl)2-[4-(2-methylpropyloxy)phenyl]-6-(ethyloxycarbonyl)pyrrolo[1,2-a]pyrimid-7-one
  参考文献：
  名称：

  A novel synthesis of 7-aryl-8-fluoro-pyrrolo[1,2-a]pyrimid-4-ones as potent, stable GnRH receptor antagonists

  摘要：

  A new class of small molecule GnRH antagonists, the 7-aryl-8-fluoro-pyrrolo[1,2-a]pyrimid-4-ones, was designed and a novel synthesis for these compounds was developed. The synthesis utilizes a base-catalyzed intramolecular cyclization of fluoromethyl pyrimidone 5 to generate the bicyclic core. Amongst the compounds synthesized, we discovered some highly potent GnRH receptor antagonists (e.g., 12. K-i = 9 nM), which showed enhanced stability towards acidic physiological conditions compared to the des-fluoro analogues. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00745-x
• 作为产物：
  描述：

  1-(4-异丁氧基苯基)乙酮 在 copper(ll) bromide 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 反应 2.0h， 以89%的产率得到α-bromo-4'-isobutoxyacetophenone
  参考文献：
  名称：

  Gonadotropin-releasing hormone receptor antagonists and methods relating thereto

  摘要：

  GnRH受体拮抗剂已被披露，可用于治疗男性和女性的各种与性激素相关的疾病。该发明的化合物具有以下结构：包括立体异构体、前药和其药用盐，其中Ar、B、R1、R2、R3a、R3b、R4、R5、R6和m的定义如本文所述。

  公开号：

  US06346534B1

文献信息

• Gonadotropin-releasing hormone receptor antagonists and methods relating thereto
  申请人：Neurocrine Biosciences, Inc.

  公开号：US06346534B1

  公开（公告）日：2002-02-12

  GnRH receptor antagonists are disclosed which have utility in the treatment of a variety of sex-hormone related conditions in both men and women. The compounds of this invention have the structure: including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof, wherein Ar, B, R1, R2, R3a, R3b, R4, R5, R6 and m are as defined herein.

  GnRH受体拮抗剂已被披露，可用于治疗男性和女性的各种与性激素相关的疾病。该发明的化合物具有以下结构：包括立体异构体、前药和其药用盐，其中Ar、B、R1、R2、R3a、R3b、R4、R5、R6和m的定义如本文所述。
• IMIDAZO- AND PYRROLO[1,2-A]PYRIMID-4-ONES AS GONADOTROPIN-RELEASING HORMONE RECEPTOR ANTAGONISTS
  申请人：Neurocrine Biosciences, Inc.

  公开号：EP1185530A1

  公开（公告）日：2002-03-13
• US4033978A
  申请人：——

  公开号：US4033978A

  公开（公告）日：1977-07-05
• [EN] IMIDAZO- AND PYRROLO[1,2-A]PYRIMID-4-ONES AS GONADOTROPIN-RELEASING HORMONE RECEPTOR ANTAGONISTS<br/>[FR] IMIDAZO- ET PYRROLO[1,2-A]PYRIMID-4-ONES UTILISES COMME ANTAGONISTES DU RECEPTEUR DE L'HORMONE DE LIBERATION DE LA GONADOTROPHINE
  申请人：NEUROCRINE BIOSCIENCES INC

  公开号：WO2000069859A1

  公开（公告）日：2000-11-23

  GnRH receptor antagonists are disclosed which have utility in the treatment of a variety of sex-hormone related conditions in both men and women. The compounds of this invention have structure (I) including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof, wherein Ar, B, R1, R2, R3a, R3b, R4, R5, R6 and m are as defined herein.
• A novel synthesis of 7-aryl-8-fluoro-pyrrolo[1,2-a]pyrimid-4-ones as potent, stable GnRH receptor antagonists
  作者：Fabio C. Tucci、Yun-Fei Zhu、Zhiqiang Guo、Timothy D. Gross、Patrick J. Connors、R.Scott Struthers、Greg J. Reinhart、Xiaochuan Wang、John Saunders、Chen Chen

  DOI：10.1016/s0960-894x(02)00745-x

  日期：2002.12

  A new class of small molecule GnRH antagonists, the 7-aryl-8-fluoro-pyrrolo[1,2-a]pyrimid-4-ones, was designed and a novel synthesis for these compounds was developed. The synthesis utilizes a base-catalyzed intramolecular cyclization of fluoromethyl pyrimidone 5 to generate the bicyclic core. Amongst the compounds synthesized, we discovered some highly potent GnRH receptor antagonists (e.g., 12. K-i = 9 nM), which showed enhanced stability towards acidic physiological conditions compared to the des-fluoro analogues. (C) 2002 Elsevier Science Ltd. All rights reserved.