dimethyl 4,4'-dimethoxy-[5,5']bi[1,3-benzodioxolyl]-6,6'-dicarboxylate | 302822-47-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: dimethyl 4,4'-dimethoxy-[5,5']bi[1,3-benzodioxolyl]-6,6'-dicarboxylate
• 英文别名: 6,6'-dimethoxy-4,5,4',5'-bis(methylenedioxy)-2,2'-bis(methoxycarbonyl)biphenyl；methyl 7-methoxy-6-(4-methoxy-6-methoxycarbonyl-1,3-benzodioxol-5-yl)-1,3-benzodioxole-5-carboxylate
• CAS: 302822-47-5
• 化学式: C₂₀H₁₈O₁₀
• 分子量: 418.357
• InChiKey: SFSNQUBKJLKHNJ-UHFFFAOYSA-N

物化性质

• 沸点：
  533.8±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 4,4'-dimethoxy-[5,5']bi[1,3-benzodioxolyl]-6,6'-dicarboxylate 在 溴 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以87%的产率得到7,7'-Dibromo-4,4'-dimethoxy-[5,5']bi[benzo[1,3]dioxolyl]-6,6'-dicarboxylic acid dimethyl ester
  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：

  没食子酸甲酯 在 盐酸 、 Sodium tetraborate decahydrate 、 sodium hydroxide 、 氢溴酸 、 硝酸 、 乙酸酐 、 铜 、 potassium carbonate 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 26.0h， 生成 dimethyl 4,4'-dimethoxy-[5,5']bi[1,3-benzodioxolyl]-6,6'-dicarboxylate
  参考文献：
  名称：

  手性联苯木质素（α-和β- DDB）的合成，分离和理论研究

  摘要：

  有效地合成了两个联苯木脂素α-和β- DDB（分别为1和2），而没有受到其他区域异构体的污染。通过计算位阻，稳定性，熵变和形成热值，可以合理地合成用于1和2合成的Ullmann偶联反应的不同收率。1和2的对映体很容易通过HPLC在手性固定相上分离。根据真实天然产品的棉花效果分配其配置。

  DOI：

  10.1002/hlca.200390180

文献信息

• Multi-functionalization of gallic acid towards improved synthesis of α- and β-DDB
  作者：Ashraful Alam、Yutaka Takaguchi、Hideyuki Ito、Takashi Yoshida、Sadao Tsuboi

  DOI：10.1016/j.tet.2004.11.083

  日期：2005.2

  The synthesis of mono-, di- and trisubstituted gallic acids and their ester with similar or different groups including different acetal and ketals is described. Regioselective bromination on two ortho-positions of methyl gallate, which is very crucial for many organic syntheses, was achieved in high yield and purity. The α- and β-DDB were synthesized in high overall yield and purity from the regioselective

  描述了具有相似或不同基团（包括不同的缩醛和缩酮）的单，二和三取代的没食子酸及其酯的合成。高产率和高纯度实现了对许多有机合成非常关键的在没食子酸甲酯的两个邻位上的区域选择性溴化。α-和β-DDB是由区域选择性溴代衍生物合成的，具有较高的总收率和纯度。
• Asymmetric Synthesis of β‐DDB Through Oxazoline‐Mediated Ullmann Coupling
  作者：Qitao Tan、Hongyan Li、Jiwu Wen、Chen Jiang、Xin Wang、Tianpa You

  DOI：10.1080/00397910500186326

  日期：2005.9.1

  Biphenyl lignan (beta-DDB) (2), an effective drug in the treatment of hepatitis, was for the first time asymmetrically synthesized via a chiral oxazoline mediated Ullmann coupling. The two enantiomers of beta-DDB have been obtained in this way by using the optically pure amino alcohols L-valinol and D-valinol, respectively. However, attempts to synthesize enantiopure alpha-DDB (1) by the same method failed because of the racemization of 1 at room temperature in solution.
• Monoacetoxylation of Methylenedioxy Groups in Dimethyl 4,4'-Dimethoxy-2,3,2',3'-bismethylenedioxy-1,1'-biphenyl-6,6'-dicarboxylate with Lead Tetraacetate
  作者：Masayuki Kimura、Yoshiyuki Matsuoka、Kunio Hosaka

  DOI：10.3987/com-92-6323

  日期：——

  The utility of lead tetraacetate as a reagent for the monoacetoxylation of a methylenedioxy group in dimethyl 4,4'-dimethoxy-2,3,2'3'-bismeth-ylenedioxy-1,1'-biphenyl-6,6'-dicarboxylate (1a) is demonstrated. Mechanistic feature of the monoacetoxylation is discussed.
• MATSUOKA, JOSIYUKI;XOSAKA, KUNIO;TAKEHDA, SIGEHFUMI;MITSUBASI, XIROSI
  作者：MATSUOKA, JOSIYUKI、XOSAKA, KUNIO、TAKEHDA, SIGEHFUMI、MITSUBASI, XIROSI

  DOI：——

  日期：——
• MATSUOKA, JOSIYUKI;XOSAKA, KUNIO;TAKEHDA, SIGEHFUMI;MIXASI, XIROSI
  作者：MATSUOKA, JOSIYUKI、XOSAKA, KUNIO、TAKEHDA, SIGEHFUMI、MIXASI, XIROSI

  DOI：——

  日期：——