2',4',6',3,4-Pentamethoxychalkone | 76650-20-9

• 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',4',6',3,4-Pentamethoxychalkone
• 英文别名: 1-(2,4,6-trimethoxyphenyl)-3-(3,4-dimethoxyphenyl)propenone；3,4,2',4',6'-pentamethoxychalcone；2',3,4,4',6'-pentamethoxychalcone；2',4',6',3,4-pentamethoxychalcone；2'.3.4.4'.6'-Pentamethoxy-chalkon；3,4,2',4',6'-Pentamethoxy-chalkon；3-(3,4-Dimethoxyphenyl)-1-(2,4,6-trimethoxyphenyl)-2-propen-1-one；3-(3,4-dimethoxyphenyl)-1-(2,4,6-trimethoxyphenyl)prop-2-en-1-one
• CAS: 76650-20-9
• 化学式: C₂₀H₂₂O₆
• 分子量: 358.391
• InChiKey: TVKGYMYAOVADOP-UHFFFAOYSA-N

物化性质

• 熔点：
  117.5 °C
• 沸点：
  538.8±50.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2',4',6',3,4-Pentamethoxychalkone 在 吡啶 、 碘 、 二甲基二环氧乙烷 、 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 22.33h， 生成 川陈皮素
  参考文献：
  名称：

  Regioselective hydroxylation of 2-hydroxychalcones by dimethyldioxirane towards polymethoxylated flavonoids

  摘要：

  The flavone nucleus is part of a large number of natural products and medicinal compounds. In this presentation the novel regioselective hydroxylation of hydroxyarenes with DMD is described. The results showed further that flavonoids with 5-hydroxy group were selectively oxyfunctionalized at the para-position C8 carbon atom by DMD. Finally, according to this methodology, the naturally occurring isosinensetin, tangeretin, sinensetin, nobiletin, natsudaidain, gardenin B, 3,3',4',5,6,7,8-heptamethoxyflavone, quercetin and its derivatives were synthesized. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.023
• 作为产物：
  描述：

  1,3,5-tris-methoxycarbonyloxy-benzene 在 三氯化铁 、 铂 作用下， 生成 2',4',6',3,4-Pentamethoxychalkone
  参考文献：
  名称：

  Freudenberg, Chemische Berichte, 1920, vol. 53, p. 1427

  摘要：

  DOI：

文献信息

• 一种羟基橙酮衍生物及其制备方法和用途
  申请人：中国科学院新疆理化技术研究所

  公开号：CN113105417A

  公开（公告）日：2021-07-13

  本发明涉及一种羟基橙酮衍生物及其制备方法和用途，以新疆昆仑雪菊中分离得到的单体化合物橙酮为母核化合物，将羟基引入到橙酮分子中，由苯乙酮衍生物和苯甲醛衍生物反应得到甲氧基查尔酮，三氯化铝条件下脱羟基保护获得2‑羟基查尔酮，醋酸汞催化反应得到含甲氧基的橙酮衍生物，三溴化硼反应脱去羟基保护得到最终产物羟基橙酮衍生物。该方法反应条件温和，实验步骤简捷。本发明所述的羟基橙酮衍生物可作为抑制死亡相关凋亡诱导蛋白激酶2（DRAK2）的药物用途。
• [EN] METHOD FOR THE SYNTHESIS OF ASPALATHIN AND ANALOGUES THEREOF<br/>[FR] PROCÉDÉ DE SYNTHÈSE D'ASPALATHINE ET DE SES ANALOGUES
  申请人：SOUTH AFRICAN MEDICAL RES COUNCIL

  公开号：WO2011064726A1

  公开（公告）日：2011-06-03

  A method of synthesising Aspalathin and its analogues or derivatives is disclosed. The method comprises synthesising a compound of formula 1 or its analogues or derivatives (I) wherein each of R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 is independently selected from the group consisting of -H, -OH, hydrocarbyl groups, saccharide moieties and -OR15; R15 is selected from the group consisting of hydrogen, a hydrocarbyl group (e.g. methoxy or ethoxy), an acyl group and a benzyl group; and R11, R12, R13 and R14 are independently selected from the group consisting of -H, hydrocarbyl groups, saccharide moieties, an acyl group and a benzyl group. The method comprises the step of coupling a sugar to a dihydrochalcone, chalcone or flavanone, or coupling the sugar to an intermediate for producing a dihydrochalcone, chalcone or flavanone followed by coupling of the sugar-intermediate adduct to a further intermediate for producing a dihydrochalcone, chalcone or flavanone, and transforming the product thereof into a compound of formula 1 or an analogue or derivative thereof.

  公开了一种合成Aspalathin及其类似物或衍生物的方法。该方法包括合成式1或其类似物或衍生物（I）的化合物，其中R1、R2、R3、R4、R5、R6、R7、R8、R9和R10中的每一个都是独立地选自-H、-OH、烃基、糖基和-OR15的群组；R15选自氢、烃基（例如甲氧基或乙氧基）、酰基和苄基的群组；R11、R12、R13和R14独立地选自-H、烃基、糖基、酰基和苄基的群组。该方法包括将糖与二氢黄烷酮、黄烷酮或黄酮偶联，或将糖与产生二氢黄烷酮、黄烷酮或黄酮的中间体偶联，然后将糖-中间体加合物与产生二氢黄烷酮、黄烷酮或黄酮的进一步中间体偶联，并将其产物转化为式1或其类似物或衍生物的化合物。
• Method for the Synthesis of Aspalathin and Analogues Thereof
  申请人：Van der Westhuizen Jan Hendrik

  公开号：US20130018182A1

  公开（公告）日：2013-01-17

  A method of synthesising Aspalathin and its analogues or derivatives is disclosed. The method comprises synthesising a compound of formula 1 or its analogues or derivatives: wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 is independently selected from the group consisting of —H, —OH, hydrocarbyl groups, saccharide moieties and —OR 15 ; R 15 is selected from the group consisting of hydrogen, a hydrocarbyl group (e.g. methoxy or ethoxy), an acyl group and a benzyl group; and R 11 , R 12 , R 13 and R 14 are independently selected from the group consisting of —H, hydrocarbyl groups, saccharide moieties, an acyl group and a benzyl group. The method comprises the step of coupling a sugar to a dihydrochalcone, chalcone or flavanone, or coupling the sugar to an intermediate for producing a dihydrochalcone, chalcone or flavanone followed by coupling of the sugar-intermediate adduct to a further intermediate for producing a dihydrochalcone, chalcone or flavanone, and transforming the product thereof into a compound of formula 1 or an analogue or derivative thereof.

  公开了一种合成Aspalathin及其类似物或衍生物的方法。该方法包括合成式1或其类似物或衍生物的化合物：其中R1、R2、R3、R4、R5、R6、R7、R8、R9和R10中的每一个都是独立选择自羟基、烃基、糖基团和—OR15的群组；R15选择自氢、烃基（例如甲氧基或乙氧基）、酰基和苄基；而R11、R12、R13和R14则独立选择自—H、烃基、糖基团、酰基和苄基的群组。该方法包括将糖与二氢黄烷酮、黄烷酮或黄酮偶联，或将糖与用于产生二氢黄烷酮、黄烷酮或黄酮的中间体偶联，然后将糖-中间体加合物偶联到用于产生二氢黄烷酮、黄烷酮或黄酮的进一步中间体上，并将其转化为式1或其类似物或衍生物的化合物。
• Horie, Tokunaru; Kawamura, Yasuhiko; Sakai, Chikako, Journal of the Chemical Society. Perkin transactions I, 1994, # 6, p. 753 - 760
  作者：Horie, Tokunaru、Kawamura, Yasuhiko、Sakai, Chikako、Akita, Ayako、Kuramoto, Masafumi

  DOI：——

  日期：——
• Kauffmann; Kieser, Chemische Berichte, 1913, vol. 46, p. 3799
  作者：Kauffmann、Kieser

  DOI：——

  日期：——