2,3-dibromo-3-(4-methoxyphenyl)propionic acid methyl ester | 91089-40-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,3-dibromo-3-(4-methoxyphenyl)propionic acid methyl ester
• 英文别名: α,β-Dibrom-β-<4-methoxy-phenyl>-propionsaeuremethylester；2,3-Dibrom-3-(4-methoxy-phenyl)-propionsaeure-methylester；Methyl 2,3-dibromo-3-(4-methoxyphenyl)propanoate
• CAS: 91089-40-6
• 化学式: C₁₁H₁₂Br₂O₃
• 分子量: 352.022
• InChiKey: YTYHVMJVZUHHMX-UHFFFAOYSA-N

物化性质

• 熔点：
  117-118 °C
• 沸点：
  347.2±42.0 °C(Predicted)
• 密度：
  1.674±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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-3-(4-methoxyphenyl)propionic acid methyl ester 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以74.6%的产率得到3-(4-甲氧基苯基)丙酸
  参考文献：
  名称：

  Efficient synthesis and biological evaluation of 4-arylcoumarin derivatives

  摘要：

  Two bioactive natural 4-arylcoumarins, 5,7,4'-trimethoxy-4-phenylcoumarin (1a), 5,7-dimethoxy-4-phenylcoumarin (1b) and five closely related derivatives 1c-g were synthesized. In vitro evaluation with a catechol subunit for antioxidant and antimicrobial activity, these compounds using standard methods showed that compounds id, if displayed promise radical scavenging activity and if was found to be the most active one against Bacillus dysenteriae. (C) 2010 Yong Zou. Published by Elsevier BAT. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2010.12.017
• 作为产物：
  描述：

  对甲氧基肉桂酸甲酯 在 氯仿 、 溴 作用下， 生成 2,3-dibromo-3-(4-methoxyphenyl)propionic acid methyl ester
  参考文献：
  名称：

  Eigel, Chemische Berichte, 1887, vol. 20, p. 2537

  摘要：

  DOI：

文献信息

• 一种1,4-二氧六环类化合物的制备方法
  申请人：云南农业大学

  公开号：CN113149954A

  公开（公告）日：2021-07-23

  本发明提供了一种1,4‑二氧六环类化合物的制备方法,属于有机药物合成技术领域，该制备方法包括一下步骤：化合物A为起始原料经过两步化学反应得到化合物C，将化合物C与邻苯二酚等原料通过环化反应可构建一系列1,4‑二氧六环结构化合物，它是一类新型的单一化合物。本发明属于首次通过全合成的方法分离纯化得到1,4‑二氧六环类化合物，该制备方法具有成分明确、纯度高等优点，对其后续结构修饰和改造以获取新型药物等研究具有重要意义。
• Spectroscopic and Computational Study of the Organocatalytic Umpolung of Bromocations: An Accelerated Stereoselective Dibromination Protocol**
  作者：Jeetendra Panda、Jigyansa Sahoo、Juhi Dutta、Himansu Sekhar Biswal、Gokarneswar Sahoo

  DOI：10.1002/chem.202300675

  日期：2023.8.10

  umpolung of cationic bromine from N-bromosuccinimide (NBS) using an amine organocatalyst is reported. The intermediate reagents and their reactivity have well been characterised by spectroscopic and computational methods. Strategic structural change in the NBS molecule can cause sufficient polarity reversal to accelerate the dibromination reaction needing both “Br” synthons. This has further been utilised

  报道了一种新开发的使用胺有机催化剂从N-溴代琥珀酰亚胺 (NBS) 中原位还原阳离子溴的方法。中间体试剂及其反应性已通过光谱和计算方法得到了很好的表征。NBS 分子的战略结构变化可以引起足够的极性反转，以加速需要两个“Br”合成子的二溴化反应。这已进一步用于具有广泛底物范围的烯烃的加速二溴化反应。
• Hariharan; Sudborough, Journal of the Indian Institute of Science, 1925, vol. <A> 8, p. 216
  作者：Hariharan、Sudborough

  DOI：——

  日期：——
• Intramolecular Nozaki–Hiyama–Kishi reactions and Ln(III)-catalyzed allylic rearrangement as the key steps towards 10-membered ring enediynes
  作者：Wei-Min Dai、Anxin Wu、Wataru Hamaguchi

  DOI：10.1016/s0040-4039(01)00707-9

  日期：2001.6

  A general and facile synthesis of the 3-substituted 10-membered ring enediynes 18-22 from the aldehydes 8 and 15 has been established by utilizing the intramolecular Nozaki-Hiyama-Kishi reaction and the lwanthanide(III)-catalyzed rearrangement of allylic alkoxyacetates as the key steps. This work provides ready access to the (E)-3-acyloxy-4-(arylmethylidene)cyclodeca-1,5-diynes, which can be converted into the bioactive enediynes under physiological conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Structure-activity relationships in 1,4-benzodioxan-related compounds. 4. Effect of aryl and alkyl substituents at position 3 on .alpha.-adrenoreceptor blocking activity
  作者：Wilma Quaglia、Maria Pigini、Seyed K. Tayebati、Alessandro Piergentili、Mario Giannella、Gabriella Marucci、Carlo Melchiorre

  DOI：10.1021/jm00063a002

  日期：1993.5

  The observation that the insertion of a phenyl ring at position 3 of WB 4101 (1) afforded a potent and selective alpha1-adrenoreceptor antagonist, phendioxan (2), prompted us to further investigate that position of the 2,3-dihydro-1,4-benzodioxin moiety. Thus the 3-phenyl of 2 was replaced by methyl, isopropyl, cyclohexyl, or para-substituted phenyl groups either in a cis or a trans relationships affording compounds 3-17 and 58. The structure of these new derivatives was assigned on the basis of the coupling constant of hydrogens at positions 2 and 3 and confirmed by a crystallographic study. The blocking activity and relative selectivity of 3-17 on alpha1- and alpha2-adrenoreceptors were evaluated in the isolated rat vas deferens. The results were compared with those obtained for 1 and 2. All the compounds, with the exception of isopropyl and cyclohexyl derivatives 5-8, were effective al-adrenoreceptor antagonists with a significant alpha1/alpha2-selectivity. The lipophilic and/or electronic character of para substituents of the 3-phenyl ring does not alter markedly the affinity toward alpha1-adrenoreceptors. However, the 3-p-tolyl derivative 10 was slightly more potent and even more selective than 2.