2-(4-bromo-phenyl)-chroman | 73110-65-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(4-bromo-phenyl)-chroman
• 英文别名: 2-(4-Bromophenyl)-3,4-dihydro-2H-1-benzopyran；2-(4-bromophenyl)-3,4-dihydro-2H-chromene
• CAS: 73110-65-3
• 化学式: C₁₅H₁₃BrO
• 分子量: 289.172
• InChiKey: WAABQZWLOKVLOK-UHFFFAOYSA-N

物化性质

• 沸点：
  384.2±41.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4-bromo-phenyl)-chroman 在 盐酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 192.0h， 生成 4-Chroman-2-yl-benzamidine; hydrochloride
  参考文献：
  名称：

  Synthesis and antirhinovirus activity of cyano and amidino substituted flavanoids

  摘要：

  Cyano and amidino flavans, isoflavans and 3(2H)-isoflavenes were synthesized in order to study their in vitro antirhinovirus activity, by comparison with the known corresponding chloro derivatives. The activity of the new compounds was evaluated on rhinovirus 1 B infected HeLa cell cultures by examining their ability to interfere with viral cytopathic effect and with plaque formation. It was found that generally the cyano derivatives behave like the chloro compounds, whereas the amidino derivatives show a lower activity, although always dependent on the position of substituent.

  DOI：

  10.1016/0223-5234(90)90191-5
• 作为产物：
  描述：

  4-溴苯乙酮 在 potassium carbonate 、 对甲苯磺酰肼 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 5.0h， 生成 2-(4-bromo-phenyl)-chroman
  参考文献：
  名称：

  Tosylhydrazine mediated conjugate reduction and sequential reductive coupling cyclization: synthesis of 2-arylchromans

  摘要：

  Tosylhydrazine mediated conjugate reduction of 2-hydroxyl chalcones and sequential reductive coupling cyclization is described. This is an unprecedented protocol and an extremely efficient method for a one-pot domino synthesis of 2-arylchromans in good to excellent yields from commercially available, cheap starting materials. More importantly, the two-step reactions can be easily controlled to afford dihydrochalcones or 2-arylchromans by the mole amounts of tosylhydrazine. Furthermore, the operational simplicity of the process and the high functional group tolerance are remarkable. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.08.027

文献信息

• Competition between Cyclization and Dehalogenation in the Photochemistry of Cinnamylphenols with Halogen Substituents at the Phenolic and Styrenic Chromophores
  作者：M. Consuelo Jiménez、Miguel A. Miranda、Rosa Tormos

  DOI：10.1021/jo971621m

  日期：1998.2.1
• Synthesis and antirhinovirus activity of cyano and amidino substituted flavanoids
  作者：C Conti、N Desideri、N Orsi、I Sestili、ML Stein

  DOI：10.1016/0223-5234(90)90191-5

  日期：1990.11

  Cyano and amidino flavans, isoflavans and 3(2H)-isoflavenes were synthesized in order to study their in vitro antirhinovirus activity, by comparison with the known corresponding chloro derivatives. The activity of the new compounds was evaluated on rhinovirus 1 B infected HeLa cell cultures by examining their ability to interfere with viral cytopathic effect and with plaque formation. It was found that generally the cyano derivatives behave like the chloro compounds, whereas the amidino derivatives show a lower activity, although always dependent on the position of substituent.
• Tosylhydrazine mediated conjugate reduction and sequential reductive coupling cyclization: synthesis of 2-arylchromans
  作者：Xuyang Shang、Xiaomeng Zhou、Wei Zhang、Changfeng Wan、Junmin Chen

  DOI：10.1016/j.tet.2015.08.027

  日期：2015.10

  Tosylhydrazine mediated conjugate reduction of 2-hydroxyl chalcones and sequential reductive coupling cyclization is described. This is an unprecedented protocol and an extremely efficient method for a one-pot domino synthesis of 2-arylchromans in good to excellent yields from commercially available, cheap starting materials. More importantly, the two-step reactions can be easily controlled to afford dihydrochalcones or 2-arylchromans by the mole amounts of tosylhydrazine. Furthermore, the operational simplicity of the process and the high functional group tolerance are remarkable. (C) 2015 Elsevier Ltd. All rights reserved.