dimethyl 7,4'-dimethoxy-[4,5']bi[1,3-benzodioxolyl]-5,6'-dicarboxylate | 79279-07-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: dimethyl 7,4'-dimethoxy-[4,5']bi[1,3-benzodioxolyl]-5,6'-dicarboxylate
• 英文别名: γ-bifendate；6,4'-dimethoxy-2,2'-dimethoxycarbonyl-4,5,5',6'-bis(methylenedioxy)biphenyl；γ-DDB；Methyl 7-methoxy-6-(7-methoxy-5-methoxycarbonyl-1,3-benzodioxol-4-yl)-1,3-benzodioxole-5-carboxylate
• CAS: 79279-07-5
• 化学式: C₂₀H₁₈O₁₀
• 分子量: 418.357
• InChiKey: YRYSPFWIMNXSOF-UHFFFAOYSA-N

物化性质

• 熔点：
  150-152 °C
• 沸点：
  569.4±50.0 °C(Predicted)
• 密度：
  1.390±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：
  108
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  dimethyl 7,4'-dimethoxy-[4,5']bi[1,3-benzodioxolyl]-5,6'-dicarboxylate 在 溴 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以82%的产率得到Methyl 6-bromo-4-(7-bromo-4-methoxy-6-methoxycarbonyl-1,3-benzodioxol-5-yl)-7-methoxy-1,3-benzodioxole-5-carboxylate
  参考文献：
  名称：

  Anti-aids agents—XXVI. Structure-activity correlations of Gomisin-G-related anti-HIV lignans from Kadsura interior and of related synthetic analogues

  摘要：

  Bioactivity-directed fractionation of an ethanolic extract of the stems of Kadsura interior led to the isolation and identification of 12 known lignans (1-12). Seven of these compounds (1, 6, 8-12) were active as anti-HIV agents. Gomisin-G (11) exhibited the most potent anti-HIV activity with EC50 and therapeutic index (TI) Values of 0.006 mu g/mL and 300, respectively. Schisantherin-D (6), kadsuranin (8), and schisandrin-C (10) showed good activity with EC50 values of 0.5, 0.8, and 1.2 mu g/mL, and TI values of 110, 56, and 33.3, respectively. Ten related synthetic biphenyl compounds, five variously substituted bismethylenedioxy, dimethoxy, and dimethoxycarbonyl isomers (18-22) and five brominated derivatives (23-27) also were evaluated for inhibitory activity against HIV-1 replication in acutely infected H9 cells. The total syntheses of two new isomers (21 and 22) are reported for the first time. The anti-HIV data indicated that the relative position and types of substituents on the phenolic hydroxy groups of either the natural lignans or the synthetic biphenyl compounds rather than the numbers of bromine(s) on the aromatic rings art of primary importance. In the cyclooctane ring of the natural lignans, the position and substitution of hydroxy groups are also important to enhanced anti-HIV activity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00118-1
• 作为产物：
  描述：

  没食子酸 在 盐酸 、 4-二甲氨基吡啶 、 Sodium tetraborate decahydrate 、 氢氧化钾 、 氯化亚砜 、 硫酸 、 氢溴酸 、 硝酸 、 铜 、 potassium carbonate 、 三乙胺 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 43.5h， 生成 dimethyl 7,4'-dimethoxy-[4,5']bi[1,3-benzodioxolyl]-5,6'-dicarboxylate
  参考文献：
  名称：

  高效合成γ-DDB。

  摘要：

  γ-DDB的合成，它是γ-DDB的另一个家族成员（二甲基4,4（'）-二甲氧基-5,6,5（'），6（'）-二亚甲基二氧基联苯-2,2（'）-二羧酸酯），进行了说明。不对称异构体（γ-DDB）通过连接子指导的分子内Ullmann偶联反应构建，然后裂解连接子并重新酯化。

  DOI：

  10.1016/j.bmcl.2004.02.055

文献信息

• An improved method for the synthesis of γ-DDB
  作者：Chuanjun Song、Peng Zhao、Zhiqiang Hu、Shuai Shi、Yanmei Cui、Junbiao Chang

  DOI：10.1016/j.bmcl.2010.01.166

  日期：2010.4

  A mild and efficient method for the synthesis γ-DDB has been developed through anhydride-linker assisted intramolecular Ullmann reaction. Highly regioselective bromination of differentially protected gallate was realized by virtue of the introduction of NBS.

  通过酸酐-连接剂辅助的分子内Ullmann反应，开发了一种温和有效的合成γ-DDB的方法。通过引入NBS实现了差异保护的没食子酸酯的高度区域选择性溴化。
• γ-联苯双酯中间体及合成方法及γ-联苯双酯合成方法
  申请人：重庆西南制药二厂有限责任公司

  公开号：CN113214299A

  公开（公告）日：2021-08-06

  本发明公开一种γ‑联苯双酯中间体及合成方法及γ‑联苯双酯合成方法，所述γ‑联苯双酯中间体为4‑甲氧基‑5,6‑亚甲二氧基‑2‑甲氧基羰基苯硼酸，基于所述γ‑联苯双酯中间体，本发明中还提供一种新的γ‑联苯双酯合成方法，不采用Ullmann反应，而是引入Suzuki‑Miyaura反应作为不对称合成的关键步骤使得合成简单且不会出现同分异构体，对制备工艺进行优化升级，减少反应步骤，优化反应条件。
• Efficient synthesis of γ -DDB
  作者：Junbiao Chang、Xiaohe Guo、Senxiang Cheng、Ruiyun Guo、Rongfeng Chen、Kang Zhao

  DOI：10.1016/j.bmcl.2004.02.055

  日期：2004.5

  Synthesis of gamma-DDB, which is another family member of gamma-DDB (dimethyl 4,4(')-dimethoxy-5,6,5('),6(')- dimethylenedioxybiphenyl-2,2(')-dicarboxylate), is described. The unsymmetric isomer (gamma-DDB) was constructed by a linker-directed intramolecular Ullmann coupling reaction, followed by the cleavage of the linker and re-esterification.

  γ-DDB的合成，它是γ-DDB的另一个家族成员（二甲基4,4（'）-二甲氧基-5,6,5（'），6（'）-二亚甲基二氧基联苯-2,2（'）-二羧酸酯），进行了说明。不对称异构体（γ-DDB）通过连接子指导的分子内Ullmann偶联反应构建，然后裂解连接子并重新酯化。
• Anti-aids agents—XXVI. Structure-activity correlations of Gomisin-G-related anti-HIV lignans from Kadsura interior and of related synthetic analogues
  作者：Dao-Feng Chen、Shun-Xiang Zhang、Lan Xie、Jing-Xi Xie、Ke Chen、Yoshiki Kashiwada、Bing-Nan Zhou、Pei Wang、L.Mark Cosentino、Kuo-Hsiung Lee

  DOI：10.1016/s0968-0896(97)00118-1

  日期：1997.8

  Bioactivity-directed fractionation of an ethanolic extract of the stems of Kadsura interior led to the isolation and identification of 12 known lignans (1-12). Seven of these compounds (1, 6, 8-12) were active as anti-HIV agents. Gomisin-G (11) exhibited the most potent anti-HIV activity with EC50 and therapeutic index (TI) Values of 0.006 mu g/mL and 300, respectively. Schisantherin-D (6), kadsuranin (8), and schisandrin-C (10) showed good activity with EC50 values of 0.5, 0.8, and 1.2 mu g/mL, and TI values of 110, 56, and 33.3, respectively. Ten related synthetic biphenyl compounds, five variously substituted bismethylenedioxy, dimethoxy, and dimethoxycarbonyl isomers (18-22) and five brominated derivatives (23-27) also were evaluated for inhibitory activity against HIV-1 replication in acutely infected H9 cells. The total syntheses of two new isomers (21 and 22) are reported for the first time. The anti-HIV data indicated that the relative position and types of substituents on the phenolic hydroxy groups of either the natural lignans or the synthetic biphenyl compounds rather than the numbers of bromine(s) on the aromatic rings art of primary importance. In the cyclooctane ring of the natural lignans, the position and substitution of hydroxy groups are also important to enhanced anti-HIV activity. (C) 1997 Elsevier Science Ltd.