3-(allyloxy)-4-bromophenol | 448956-67-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(allyloxy)-4-bromophenol
• 英文别名: 4-bromo-3-prop-2-enoxyphenol
• CAS: 448956-67-0
• 化学式: C₉H₉BrO₂
• 分子量: 229.073
• InChiKey: BCNRBMXLRDRCIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  3-(allyloxy)-4-bromophenol 在 四(三苯基膦)钯 、 苯硅烷 、 potassium carbonate 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-Bromo-5-(4-(((2,4-difluorobenzyl)(2-methyl-3-nitrophenyl)amino)methyl)phenoxy)phenol
  参考文献：
  名称：

  Antidiabetic Activity of Passive Nonsteroidal Glucocorticoid Receptor Modulators

  摘要：

  Much has been learned about the consequences of glucocorticoid receptor antagonism by studying steroidal active antagonists such as RU-38486 (1). In the liver glucocorticoid receptor antagonism suppresses hepatic glucose production decreasing plasma glucose levels; however, extrahepatic antagonism produces several undesirable side effects including activation of the hypothalamic pituitary adrenal axis. A series of nonsteroidal passive N-(3-dibenzylamino-2-alkyl-phenyl)-methanesulfonamide glucocorticoid receptor modulators was discovered. Liver selective and systemically available members of this series were found and characterized in diabetes and side effect rodent models. A highly liver selective member of this series, acid 14, shows efficacy in the ob/ob model of diabetes. It lowers plasma glucose, cholesterol, and free fatty acid concentrations and reduces the rate of body weight gain. The structurally related systemically available passive modulator 12 lowers glucose, HbA(1c), triglyceride, free fatty acid, and cholesterol levels. Interestingly, it did not acutely activate the hypothalamic pituitary adrenal axis in unstressed CD-1 mice or have the abortive effects observed with 1. These results indicate that passive GR antagonists may have utility as antidiabetic agents.

  DOI：

  10.1021/jm050205o
• 作为产物：
  描述：

  3-(2-Propenoxy)cyclohex-2-en-1-one 在 六甲基磷酰三胺 、 lithium hexamethyldisilazane 、 4-甲基苯磺酰溴 作用下， 以 四氢呋喃 为溶剂， 反应 1.83h， 以86%的产率得到3-(allyloxy)-4-bromophenol
  参考文献：
  名称：

  酒类酯的区域发散性卤化：一锅，无过渡金属的分化卤代间苯二酚的访问。

  摘要：

  我们报告了一种高效的方法，用于使用容易获得的乙烯基酯和磺酰卤卤素供体进行卤代间苯二酚衍生物的区域发散合成。4-或6-卤代间苯二酚异构体可从常见的前体获得。与用于芳烃卤化的常规氧化剂相比，温和的磺酰卤具有广泛的官能团相容性。该策略固有地区分了两个间苯二酚氧原子，并增强了复杂分子合成的潜力。

  DOI：

  10.1021/ol503561x

文献信息

• Glucocorticoid receptor modulators
  申请人：——

  公开号：US20020156311A1

  公开（公告）日：2002-10-24

  Compounds of formula (I) 1 or pharmaceutically acceptable salts thereof are novel glucocorticoid receptor modulators and are useful for treating type II diabetes in a mammal.

  化合物的结构式（I）1或其药学上可接受的盐是新型糖皮质激素受体调节剂，可用于治疗哺乳动物的II型糖尿病。
• Practical regioselective halogenation of vinylogous esters: synthesis of differentiated mono-haloresorcinols and polyhalogenated resorcinols
  作者：Xiaohong Chen、Xiaoguang Liu、Jenny S. Martinez、Justin T. Mohr

  DOI：10.1016/j.tet.2016.02.006

  日期：2016.6

  A practical and efficient method for the direct, regioselective conversion of vinylogous esters to haloresorcinols is reported. Control of the reaction conditions enables synthesis of either the 4- or 6-haloresorcinol isomers from a common precursor with excellent regiocontrol and high yield. The generality and functional group tolerance of this novel protocol is demonstrated. The utility of this methodology

  报道了一种实用有效的方法，用于将乙烯基酯直接，区域选择性地转化为卤代间苯二酚。控制反应条件使得能够从普通前体中以优异的区域控制和高产率合成4-或6-卤代间苯二酚异构体。证明了这种新颖的协议的普遍性和官能团耐受性。还报道了该方法用于获得多卤代间苯二酚的实用性。这些方法为进一步的合成应用创建了有用的功能化构建基块。
• GLUCOCORTICOID RECEPTOR MODULATORS
  申请人：KARO BIO AB

  公开号：EP1363876B1

  公开（公告）日：2009-07-29
• US6583180B2
  申请人：——

  公开号：US6583180B2

  公开（公告）日：2003-06-24
• Regiodivergent Halogenation of Vinylogous Esters: One-Pot, Transition-Metal-Free Access to Differentiated Haloresorcinols
  作者：Xiaohong Chen、Jenny S. Martinez、Justin T. Mohr

  DOI：10.1021/ol503561x

  日期：2015.1.16

  vinylogous esters and sulfonyl halide halogen donors. Either the 4- or 6-haloresorcinol isomer is accessible from a common precursor. In contrast to conventional oxidants for arene halogenation, mild sulfonyl halides allow broad functional group compatibility. The strategy inherently differentiates the two resorcinol oxygen atoms and enhances the potential for complex molecule synthesis.

  我们报告了一种高效的方法，用于使用容易获得的乙烯基酯和磺酰卤卤素供体进行卤代间苯二酚衍生物的区域发散合成。4-或6-卤代间苯二酚异构体可从常见的前体获得。与用于芳烃卤化的常规氧化剂相比，温和的磺酰卤具有广泛的官能团相容性。该策略固有地区分了两个间苯二酚氧原子，并增强了复杂分子合成的潜力。