2,3-dibromo-1,3-bis(4-methoxyphenyl)propan-1-one | 59258-25-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2,3-dibromo-1,3-bis(4-methoxyphenyl)propan-1-one
• 英文别名: 2,3-dibromo-1,3-bis-(4-methoxy-phenyl)-propan-1-one；2,3-Dibrom-1,3-bis-(4-methoxy-phenyl)-propan-1-on；1-Propanone, 2,3-dibromo-1,3-bis(4-methoxyphenyl)-
• CAS: 59258-25-2
• 化学式: C₁₇H₁₆Br₂O₃
• 分子量: 428.12
• InChiKey: DTAHPGMKUAKDKW-UHFFFAOYSA-N

物化性质

• 熔点：
  140 °C (decomp)
• 沸点：
  501.0±50.0 °C(Predicted)
• 密度：
  1.564±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  2,3-dibromo-1,3-bis(4-methoxyphenyl)propan-1-one 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 甲醇 为溶剂， 反应 0.42h， 以88%的产率得到4,4’-二甲氧基查耳酮
  参考文献：
  名称：

  Stereoselective debromination and selective reduction of vic-dibromides with nickel boride

  摘要：

  报告了在常温下用硼化物镍对沧二溴化物进行立体选择性脱溴反应的简单程序。此外，还报道了脱溴同时还原沧二溴化物以得到二氢化产物的一锅反应。α，β-二溴酮也可以转化为相应的醇。

  DOI：

  10.1139/v06-125
• 作为产物：
  描述：

  4,4’-二甲氧基查耳酮 在 二硫化碳 、 溴 作用下， 生成 2,3-dibromo-1,3-bis(4-methoxyphenyl)propan-1-one
  参考文献：
  名称：

  Straus, Justus Liebigs Annalen der Chemie, 1906, vol. 347, p. 140

  摘要：

  DOI：

文献信息

• Design, synthesis and biological evaluation of bis(hydroxyphenyl) azoles as potent and selective non-steroidal inhibitors of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1) for the treatment of estrogen-dependent diseases
  作者：Emmanuel Bey、Sandrine Marchais-Oberwinkler、Patricia Kruchten、Martin Frotscher、Ruth Werth、Alexander Oster、Oztekin Algül、Alexander Neugebauer、Rolf W. Hartmann

  DOI：10.1016/j.bmc.2008.04.073

  日期：2008.6

  The combination of a ligand- and a structure-based drug design approach led to the identification of bis(hydroxyphenyl) azoles as potential inhibitors of 17beta-HSD1. Different azoles and hydroxy substitution patterns were investigated. The compounds were evaluated for activity and selectivity with regard to 17beta-HSD2, ERalpha and ERbeta. The most potent compound is 3-[5-(4-hydroxyphenyl)-1,3-oxazol-2-yl]phenol

  17beta-羟基类固醇脱氢酶1（17beta-HSD1）催化将活性较弱的雌酮（E1）还原为最有效的雌激素17beta-雌二醇（E2）。E2通过激活雌激素受体（ER）刺激激素依赖性疾病的生长。17beta-HSD1通常在乳腺癌细胞中过表达。因此，它是治疗乳腺肿瘤的有吸引力的靶标。配体和基于结构的药物设计方法的结合导致了对双（羟苯基）唑类化合物作为17β-HSD1潜在抑制剂的鉴定。研究了不同的唑和羟基取代方式。评估了化合物相对于17beta-HSD2，ERalpha和ERbeta的活性和选择性。最有效的化合物是3- [5-（4-羟基苯基）-1,3-恶唑-2-基]苯酚（18，IC（50）= 0.31 microM），
• Jakhar, Komal; Makrandi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 1, p. 141 - 145
  作者：Jakhar, Komal、Makrandi

  DOI：——

  日期：——
• Photocatalytic Dehalogenation of Vicinal Dibromo Compounds Utilizing Sexithiophene and Visible-Light Irradiation
  作者：Christopher D. McTiernan、Spencer P. Pitre、Juan C. Scaiano

  DOI：10.1021/cs501030f

  日期：2014.11.7

  The reductive dehalogenation of a variety of vicinal-dibromide compounds has been accomplished through the use of a-sexithiophene as an organophotocatalyst. This photocatalytic system brings about the desired transformations in good yields, using low catalyst loadings and short reaction times. To help shed light on the efficiency of this process, we have studied the kinetics of the key mechanistic steps utilizing a combination of steady-state/time-resolved fluorescence and laser flash photolysis techniques.
• 1,3-Diphenylpropane-1,3-diamines XII [1]. A Novel Approach to Stereodefined Oximes and Oxime Ethers of Monothioketalized 1,3-Diketones and their Conversion to 3-Aminooximes
  作者：Alexander Kaiser、Wolfgang Wiegrebe

  DOI：10.1007/pl00013502

  日期：1998.9

  Mono-O,O- and mono-S,S-ketals of 1,3-diphenylpropane-1,3-diones react with hydroxylamine hydrochloride and O-methylhydroxylamine hydrochloride affording mixtures of (E/Z) isomers which are hard to separate or an even unseparable. Isomerically pure oximes and O-methyloximes, however, are obtained either from 2-lithiated 1,3-dithianes and alpha-halogeno-oximes and alpha-halogeno-oxime ethers, resp., or from lithiated oxime ethers and dithienium salts. Reduction, acetylation, hydrolysis of the ketal increment, and oximation afford 3-amino-oximes which are precursors of 1,3-diphenylpropane-1,3-diamines.
• Human estrogen receptor α antagonists, part 2: Synthesis driven by rational design, in vitro antiproliferative, and in vivo anticancer evaluation of innovative coumarin-related antiestrogens as breast cancer suppressants
  作者：Nezrina Kurtanović、Nevena Tomašević、Sanja Matić、Marina M. Mitrović、Danijela A. Kostić、Manuela Sabatino、Lorenzo Antonini、Rino Ragno、Milan Mladenović

  DOI：10.1016/j.ejmech.2021.113869

  日期：2022.1