5-[1-[4-[(3-bromophenyl)methoxy]phenyl]but-2-ynyl]-2,2-dimethyl-1,3-dioxane-4,6-dione | 1204473-97-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-[1-[4-[(3-bromophenyl)methoxy]phenyl]but-2-ynyl]-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 1204473-97-1
• 化学式: C₂₃H₂₁BrO₅
• 分子量: 457.321
• InChiKey: ZAVKMKIEWZJXGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  5-(4-(3-bromobenzyloxy)benzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 、 1-丙炔溴化镁 生成 5-[1-[4-[(3-bromophenyl)methoxy]phenyl]but-2-ynyl]-2,2-dimethyl-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  Asymmetric syntheses of a GPR40 receptor agonist via diastereoselective and enantioselective conjugate alkynylation

  摘要：

  Two asymmetric methods to synthesize a potent GPR40 receptor agonist are reported. Both synthetic routes utilize readily available, inexpensive starting materials and reagents. The first route relies on a highly diastereoselective conjugate alkynylation of an ephedrine-derived oxazepanedione acceptor. The second route features the enantioselective alkynylation of a Meldrum's acid-derived acceptor mediated by a chiral zinc cinchonidine reagent. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.019

文献信息

• Practical Asymmetric Conjugate Alkynylation of Meldrum’s Acid-Derived Acceptors: Access to Chiral β-Alkynyl Acids
  作者：Sheng Cui、Shawn D. Walker、Jacqueline C. S. Woo、Christopher J. Borths、Herschel Mukherjee、Maosheng J. Chen、Margaret M. Faul

  DOI：10.1021/ja909105s

  日期：2010.1.20

  The enantioselective conjugate addition of alkynyl nucleophiles has been a long-standing challenge in synthetic chemistry. This paper describes a highly practical asymmetric conjugate alkynylation of Meldrum's acid-derived acceptors using cinchonidine (<$100/kg) as the chiral mediator. The process provides practical access to chiral beta-alkynyl acids. Noteworthy attributes of the method are its broad

  炔基亲核试剂的对映选择性共轭加成一直是合成化学中长期存在的挑战。本文描述了使用辛可尼丁 (<$100/kg) 作为手性介质的 Meldrum 酸衍生受体的高度实用的不对称共轭炔基化。该过程提供了获得手性β-炔基酸的实际途径。该方法的值得注意的属性是其广泛的范围、高度的功能组兼容性和易于扩展。