6-bromo-2-phenylchroman | 73110-76-6

• 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: 6-bromo-2-phenylchroman
• 英文别名: 6-bromo-2-phenyl-3,4-dihydro-2H-chromene
• CAS: 73110-76-6
• 化学式: C₁₅H₁₃BrO
• 分子量: 289.172
• InChiKey: RRGWEMYJPYYMHQ-UHFFFAOYSA-N

物化性质

• 沸点：
  389.7±42.0 °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：

  6-bromo-2-phenylchroman 在 盐酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 193.0h， 生成
  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：

  5-bromo-2-(methoxymethoxy)benzaldehyde 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 p-toluenesulfonic acid on sillica gel 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 6-bromo-2-phenylchroman
  参考文献：
  名称：

  Pt（IV）催化邻醌甲基化物的生成和[4 + 2]-环加成反应

  摘要：

  已经开发了新的分子间和分子内生成的邻醌甲基化物及其在温和条件下与PtCl 4和AuCl 3催化的烯烃的正式[4 + 2]-环加成反应。获得了良好的品色（高达99％）和非对映体选择性（高达> 99：1）的苯并二氢吡喃。发现PtCl 4是有效的并且与存在于底物中的各种官能团相容。提出并讨论了其催化循环的机理。

  DOI：

  10.1016/j.tet.2011.03.059

文献信息

• Generation of <i>ortho</i>-Quinone Methides by <i>p</i>-TsOH on Silica and Their Hetero-Diels−Alder Reactions with Styrenes
  作者：Paratchata Batsomboon、Wong Phakhodee、Somsak Ruchirawat、Poonsakdi Ploypradith

  DOI：10.1021/jo900504y

  日期：2009.5.15

  2-Arylchromans were readily prepared from the hetero-Diels−Alder reactions of styrenes with the ortho-quinone methides (o-QMs) which, in turn, were generated by treating the MOM-protected benzylacetate derivatives with p-TsOH immobilized on silica (PTS-Si) in toluene under mild conditions (0 °C to rt). The corresponding chromans were obtained in moderate to excellent yields (42−97%) and in moderate

  从苯乙烯与邻-醌甲基化物（o- QMs）的杂Diels-Alder反应可以很容易地制备2-芳基苯并二氢吡喃，这些反过来又是通过用固定在二氧化硅上的p -TsOH处理MOM保护的苄基乙酸酯衍生物而制得的（在温和条件下（0°C至rt）在甲苯中的PTS-Si）。以中等至极好的收率（42-97％）和中等至极好的非对映选择性（高达> 99：1）获得了相应的色度。
• Moderately lipophilic 2-(Het)aryl-6-dithioacetals, 2-phenyl-1,4-benzodioxane-6-dithioacetals and 2-phenylbenzofuran-5-dithioacetals: Synthesis and primary evaluation as potential antidiabetic AMPK-activators
  作者：Veronica Lepechkin-Zilbermintz、Daniel Bareket、Virginie Gonnord、Alexandre Steffen、Christophe Morice、Mathieu Michaut、Anna Munder、Edward E. Korshin、Jean-Marie Contreras、Erol Cerasi、Shlomo Sasson、Arie Gruzman

  DOI：10.1016/j.bmc.2023.117303

  日期：2023.5

  at least partially, AMPK activation for its therapeutic effect. Herein we present design and synthesis of 20 novel relatively polar cyclic and acyclic dithioacetals of 2-(Het)arylchroman-6-carbaldehydes, 2-phenyl-1,4-benzodioxane-6-carbaldehyde, and 2-phenylbenzofuran-5-carbaldehyde, which were developed as potential AMPK activators. Three of the synthesized dithioacetals demonstrated significant enhancement

  自 1950 年代以来，AMP 激酶 (AMPK) 已被用作开发针对2 型糖尿病(T2D) 的抗糖尿病药物的有前途的靶标。事实上，典型的抗糖尿病药物二甲双胍至少部分地招募了 AMPK 激活以达到其治疗效果。在这里，我们介绍了 20 种新型相对极性的环状和非环状二硫缩醛的 2-(Het)arylchroman-6-carbaldehydes、2-phenyl-1,4-benzodioxane-6-carbaldehyde 和 2-phenylbenzofuran-5-carbaldehyde 的设计和合成，被开发为潜在的AMPK 激活剂。三种合成的二硫缩醛表现出葡萄糖摄取的显着增强 (≥70%)在大鼠 L6 肌管中。值得注意的是，与其他分子相比，其中一种二硫缩醛，即 4-(6-(1,3-dithian-2-yl)chroman-2-yl)pyridine 表现出高效能。它增加大鼠 L6 肌管的葡萄糖摄取率，并增加大鼠
• 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
• Pt(IV)-catalyzed generation and [4+2]-cycloaddition reactions of o-quinone methides
  作者：Suttipol Radomkit、Pakornwit Sarnpitak、Jumreang Tummatorn、Paratchata Batsomboon、Somsak Ruchirawat、Poonsakdi Ploypradith

  DOI：10.1016/j.tet.2011.03.059

  日期：2011.5

  Novel intermolecular and intramolecular generations of ortho-quinone methides and their formal [4+2]-cycloaddition reactions with olefins catalyzed by PtCl4 and AuCl3 under mild conditions have been developed. Good to excellent yields (up to 99%) and diastereoselectivity (up to >99:1) of the chromans were obtained. PtCl4 was found to be effective and compatible with various functional groups present

  已经开发了新的分子间和分子内生成的邻醌甲基化物及其在温和条件下与PtCl 4和AuCl 3催化的烯烃的正式[4 + 2]-环加成反应。获得了良好的品色（高达99％）和非对映体选择性（高达> 99：1）的苯并二氢吡喃。发现PtCl 4是有效的并且与存在于底物中的各种官能团相容。提出并讨论了其催化循环的机理。
• 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.