5,6,7-trimethoxy-4-(4-methoxyphenyl)-3,4-dihydrochromen-2-one | 267901-34-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 5,6,7-trimethoxy-4-(4-methoxyphenyl)-3,4-dihydrochromen-2-one
• 英文别名: 3,4-dihydro-4-(4-methoxyphenyl)-5,6,7-trimethoxycoumarin；5,6,7-trimethoxy-4-(4-methoxyphenyl)chroman-2-one
• CAS: 267901-34-8
• 化学式: C₁₉H₂₀O₆
• 分子量: 344.364
• InChiKey: SESJRUNSSITKMH-UHFFFAOYSA-N

物化性质

• 熔点：
  96.7-97.4 °C
• 沸点：
  452.7±45.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,6,7-trimethoxy-4-(4-methoxyphenyl)-3,4-dihydrochromen-2-one 在 三氟化硼乙醚 、 苯硅烷 作用下， 以 二氯甲烷 、 二丁醚 、 甲苯 为溶剂， 反应 3.0h， 生成 (+/-)-trans-5,6,7-trimethoxy-4-(4-methoxyphenyl)-2-phenylchroman
  参考文献：
  名称：

  立体化学控制2-苯并二氢吡喃醇的还原。

  摘要：

  [反应：见正文]还原C5取代的2-羟基苯并二氢吡喃选择性地使用较大的硅烷还原剂提供2,4-顺式苯并二氢吡喃，并使用较小的硅烷PhSiH（3）进行2,4-反式-苯并二氢吡喃。立体化学结果已根据Curtin-Hammett动力学情况进行了合理化，该动力学情况是由氢化物传递至中间体氧碳鎓离子的两个不同构象而引起的。该方法提供了一种有效的方法来控制这些在生物活性天然产物中普遍存在的亚结构的相对立体化学。

  DOI：

  10.1021/ol061727g
• 作为产物：
  描述：

  (E)-3,4,5-trimethoxyphenyl 3-(4-methoxyphenyl)acrylate 在 三氟乙酸 作用下， 反应 18.0h， 以99%的产率得到5,6,7-trimethoxy-4-(4-methoxyphenyl)-3,4-dihydrochromen-2-one
  参考文献：
  名称：

  Trifluoroacetic Acid-Mediated Hydroarylation:  Synthesis of Dihydrocoumarins and Dihydroquinolones

  摘要：

  Trifluoroacetic acid mediates the hydroarylation of alkenes to afford dihydrocoumarins and dihydroquinolones in good yield. Intermolecular hydroarylation of cinnamic acids by phenols is particularly facile, which leads to the conclusion that previous reports of palladium-catalyzed hydroarylation of cinnamic acids in trifluoroacetic acid are erroneous.

  DOI：

  10.1021/jo0477650

文献信息

• Hexafluoroisopropanol and Acetyl Chloride Promoted Catalytic Hydroarylation with Phenols
  作者：Sudeshna Roy、Hashim F. Motiwala、Karl M. Koshlap、Jeffrey Aubé

  DOI：10.1002/ejoc.201701256

  日期：2018.1.23

  HFIP facilitates the mild catalytic hydroarylation of phenols to provide dihydrocoumarins using sub‐stoichiometric amounts of acetyl chloride as catalyst.

  HFIP促进了酚的轻度催化加氢芳基化反应，从而使用亚化学计量的乙酰氯作为催化剂提供了二氢香豆素。
• Substituted 4h-chromens, 2h-chromenes, chromans and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：Cai Xiong Sui

  公开号：US20050176750A1

  公开（公告）日：2005-08-11

  The present invention is directed to substituted 4H-chromenes, 2H-chromenes, chromans and analogs thereof, represented by the general Formula (I) wherein R 5 , A, B, X, Y, Z and dotted lines are defined herein. The present invention also relates to the discovery that compounds having Formula (I) are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention can be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及被代替的4H-色烯、2H-色烯、色烷及其类似物，由通式（I）所表示，其中R5、A、B、X、Y、Z和虚线在此定义。本发明还涉及发现具有通式（I）的化合物是caspase的激活剂和凋亡的诱导剂。因此，本发明的caspase激活剂和凋亡诱导剂可用于诱导在各种临床情况下出现的异常细胞的无控制生长和扩散的细胞死亡。
• New Method for Preparation of Coumarins and Quinolinones via Pd-Catalyzed Intramolecular Hydroarylation of C−C Triple Bonds
  作者：Chengguo Jia、Dongguo Piao、Tsugio Kitamura、Yuzo Fujiwara

  DOI：10.1021/jo000861q

  日期：2000.11.1

  A new and general method has been developed for preparation of coumarins and quinolinones by intramolecular hydroarylation of alkynes. Various aryl alkynoates and alkynanilides undergo fast intramolecular reaction at room temperature in the presence of a catalytic amount of Pd(OAc)(2) in a mixed solvent containing trifluoroacetic acid (TFA), affording coumarins and quinolinones in moderate to excellent yields with more than 1000 turnover numbers (TON) to Pd. The methodology proved to tolerate a number of functional groups such as Br and CHO. On the basis of isotope experiments, a possible mechanism involving ethynyl chelation-assisted electrophilic metalation of aromatic C-H bonds by in-situ generated cationic Pd(II) species has been discussed. Also the involvement of vinylcationic species has been suggested.
• SUBSTITUTED 4H-CHROMENES, 2H-CHROMENES, CHROMANS AND ANALOGS AS ACTIVATORS OF CASPASES AND INDUCERS OF APOPTOSIS AND THE USE THEREOF
  申请人：Cytovia, Inc.

  公开号：EP1513515A2

  公开（公告）日：2005-03-16
• US7476741B2
  申请人：——

  公开号：US7476741B2

  公开（公告）日：2009-01-13