ethyl 2'-chlorocarbonyl-4,4'-dimethoxy-5,6,5',6'-dimethylenedioxy-biphenyl-2-carboxylate | 502621-96-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: ethyl 2'-chlorocarbonyl-4,4'-dimethoxy-5,6,5',6'-dimethylenedioxy-biphenyl-2-carboxylate
• 英文别名: Ethyl 4-(5-carbonochloridoyl-7-methoxy-1,3-benzodioxol-4-yl)-7-methoxy-1,3-benzodioxole-5-carboxylate
• CAS: 502621-96-7
• 化学式: C₂₀H₁₇ClO₉
• 分子量: 436.803
• InChiKey: GXWLEVMNOKTGGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-amino-3-[(4-phenylphenyl)methoxyimino]propan-1-ol 、 ethyl 2'-chlorocarbonyl-4,4'-dimethoxy-5,6,5',6'-dimethylenedioxy-biphenyl-2-carboxylate 以90%的产率得到ethyl 4-[5-[[(3E)-1-hydroxy-3-[(4-phenylphenyl)methoxyimino]propan-2-yl]carbamoyl]-7-methoxy-1,3-benzodioxol-4-yl]-7-methoxy-1,3-benzodioxole-5-carboxylate
  参考文献：
  名称：

  A solid-phase approach to DDB derivatives

  摘要：

  Since the discovery of 2,2'-dimethoxycarbonyl-4,4-dimethoxy-5,6,5',6'-biomethylenedioxy-biphenyl (DDB) as a potent anti-HBV agent, we have studied the structure-activity relationships of 4,4'-dimethoxy -5,6,5',6'-dimethenedioxy-2-alkyloxycarbonyl-2'-(4- substituted benzyl piperazin-1-yl)carbonyl-biphenyl as anti-HBV agents. Therefore, it is rational to extend this study to the 3,3'-disustituted-4,4'-dimethoxy5,6,5',6'-dimethenedioxy-2-alkyloxycarbonyl-2'-Serine derivatives. Thus, in an attempt to develop an efficient method for the preparation of a large number of DDB derivatives, the reaction between a DDB acid chloride and serine derivatives on solid support was studied. The structure of resulted compounds was confirmed by LC-MS and H-1 NMR analysis. Compounds 2a, 2d, 2f, 2j showed in vitro anti-HBV activity without significant toxicity up to 100 mu M. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.03.024
• 作为产物：
  描述：

  7,7'-Dimethoxy-[4,4']bi[benzo[1,3]dioxolyl]-5,5'-dicarboxylic acid 5-ethyl ester 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 ethyl 2'-chlorocarbonyl-4,4'-dimethoxy-5,6,5',6'-dimethylenedioxy-biphenyl-2-carboxylate
  参考文献：
  名称：

  通过结晶诱导的构型转变以简便的方式制备的轴向手性联苯的绝对构型和CD光谱

  摘要：

  轴向手性联苯如（M，S）‐ 3k可通过将其非对映异构体混合物结晶而方便地获得，它们是由外消旋4,4'-二甲氧基-5,6,5'，6'-双（亚甲基二氧基）-合成的2-羧酸酯基-2'-羧基联苯4个手性氨基醇（[R）-alaninol，（小号）-alaninol，（小号） -缬氨醇，和（小号） -苯丙氨醇。由此实现了联苯的结晶诱导构型转变。发现（S）-缬氨醇或（S的酰胺形成）联苯2'-位处的苯丙氨醇通常会诱导乙醇中具有（M）构型的晶体沉积，产率高于50％。X射线晶体学分析确定了两个结晶联苯的绝对构型（AC）。九个联苯的AC已根据其CD光谱进行分配。此外，对这些轴向手性联苯的稳定性研究表明，AC可以在重新溶解后还原。能量势垒，以（差向异构化之间P，- [R ）-图3b和（中号，- [R ）- 3b中被测量为Δ G ^ ＃= 21.45 kcal / mol，在301 K下的乙醇半衰期为17.1 h。手性，2010年。©2010

  DOI：

  10.1002/chir.20828

文献信息

• A solid-phase approach to DDB derivatives
  作者：Xiuxiang Qi、Xiaolai Wang、Limin Wang、Qiang Wang、Senxiang Cheng、Jishuan Suo、Junbiao Chang

  DOI：10.1016/j.ejmech.2005.03.024

  日期：2005.8

  Since the discovery of 2,2'-dimethoxycarbonyl-4,4-dimethoxy-5,6,5',6'-biomethylenedioxy-biphenyl (DDB) as a potent anti-HBV agent, we have studied the structure-activity relationships of 4,4'-dimethoxy -5,6,5',6'-dimethenedioxy-2-alkyloxycarbonyl-2'-(4- substituted benzyl piperazin-1-yl)carbonyl-biphenyl as anti-HBV agents. Therefore, it is rational to extend this study to the 3,3'-disustituted-4,4'-dimethoxy5,6,5',6'-dimethenedioxy-2-alkyloxycarbonyl-2'-Serine derivatives. Thus, in an attempt to develop an efficient method for the preparation of a large number of DDB derivatives, the reaction between a DDB acid chloride and serine derivatives on solid support was studied. The structure of resulted compounds was confirmed by LC-MS and H-1 NMR analysis. Compounds 2a, 2d, 2f, 2j showed in vitro anti-HBV activity without significant toxicity up to 100 mu M. (c) 2005 Elsevier SAS. All rights reserved.
• Absolute configurations and CD spectra of axially chiral biphenyls prepared in a facile manner by crystallization-induced configuration transformation
  作者：Limin Wang、Senxiang Cheng、Rongfeng Chen、Junbiao Chang

  DOI：10.1002/chir.20828

  日期：——

  the biphenyls was thus achieved. It was found that amide formation of an (S)‐valinol or (S)‐phenylalaninol at the 2′‐position of the biphenyl usually induced the deposition of crystals with the (M)‐configuration from ethanol in yields higher than 50%. The absolute configurations (ACs) of two crystalline biphenyls have been determined by X‐ray crystallographic analysis. The ACs of nine biphenyls have been

  轴向手性联苯如（M，S）‐ 3k可通过将其非对映异构体混合物结晶而方便地获得，它们是由外消旋4,4'-二甲氧基-5,6,5'，6'-双（亚甲基二氧基）-合成的2-羧酸酯基-2'-羧基联苯4个手性氨基醇（[R）-alaninol，（小号）-alaninol，（小号） -缬氨醇，和（小号） -苯丙氨醇。由此实现了联苯的结晶诱导构型转变。发现（S）-缬氨醇或（S的酰胺形成）联苯2'-位处的苯丙氨醇通常会诱导乙醇中具有（M）构型的晶体沉积，产率高于50％。X射线晶体学分析确定了两个结晶联苯的绝对构型（AC）。九个联苯的AC已根据其CD光谱进行分配。此外，对这些轴向手性联苯的稳定性研究表明，AC可以在重新溶解后还原。能量势垒，以（差向异构化之间P，- [R ）-图3b和（中号，- [R ）- 3b中被测量为Δ G ^ ＃= 21.45 kcal / mol，在301 K下的乙醇半衰期为17.1 h。手性，2010年。©2010