3,4,5-Trimethoxycarbonyloxybenzoylchlorid | 141992-37-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4,5-Trimethoxycarbonyloxybenzoylchlorid
• 英文别名: 3,4,5-tris-methoxycarbonyloxy-benzoyl chloride；3.4.5-Tris-(carbomethoxy-oxy)-benzoylchlorid；Tricarbomethoxygalloylchlorid；Gallussaeurechlorid-O³.O⁴.O⁵-tris-carbonsaeuremethylester；Tricarbomethoxy-galloylchlorid；[4-carbonochloridoyl-2,6-bis(methoxycarbonyloxy)phenyl] methyl carbonate
• CAS: 141992-37-2
• 化学式: C₁₃H₁₁ClO₁₀
• 分子量: 362.677
• InChiKey: NRCNOZOYQYYWQE-UHFFFAOYSA-N

物化性质

• 熔点：
  86 °C
• 沸点：
  503.6±50.0 °C(Predicted)
• 密度：
  1.463±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,4,5-Trimethoxycarbonyloxybenzoylchlorid 在 Pd-BaSO₄ 、 xylene 作用下， 生成 3,4,5-tris-methoxycarbonyloxy-benzaldehyde
  参考文献：
  名称：

  Untersuchungen in der Kumarinreihe. 2. Synthese einiger Kumarinaldehyde; mit Bemerkungen über die katalytische Hydrierung der Säurechloride

  摘要：

  DOI：

  10.1002/ardp.19332710808
• 作为产物：
  描述：

  3,4,5-tris[(methoxycarbonyl)oxy]benzoic acid 在 五氯化磷 作用下， 生成 3,4,5-Trimethoxycarbonyloxybenzoylchlorid
  参考文献：
  名称：

  Fischer,E., Chemische Berichte, 1908, vol. 41, p. 2872

  摘要：

  DOI：

文献信息

• Heinisch; Ulbricht; Willitzer, Arzneimittel-Forschung/Drug Research, 1992, vol. 42, # 5, p. 668 - 673
  作者：Heinisch、Ulbricht、Willitzer、Hanschke、Tresselt、Mollmann、Eckardt、Haupt

  DOI：——

  日期：——
• Structure−Activity Relationships:  Analogues of the Dicaffeoylquinic and Dicaffeoyltartaric Acids as Potent Inhibitors of Human Immunodeficiency Virus Type 1 Integrase and Replication
  作者：Peter J. King、Guoxiang Ma、Wenfang Miao、Qi Jia、Brenda R. McDougall、Manfred G. Reinecke、Chris Cornell、Jean Kuan、Tracey R. Kim、W. Edward Robinson

  DOI：10.1021/jm9804735

  日期：1999.2.1

  The dicaffeoylquinic acids (DCQAs) and dicaffeoyltartaric acids (DCTAs) are potent and selective inhibitors of human immunodeficiency virus type 1 (HIV-1) integrase. They also inhibit HIV-1 replication at nontoxic concentrations; Since integrase is an excellent target for anti-HIV therapy, structure-activity relationships were employed to synthesize compounds with: (1) improved potency against HIV-1 integrase, (2) improved anti-HIV effect in tissue culture, and (3) increased selectivity as indicated by low cellular toxicity. Thirty-four analogues of the DCTAs and DCQAs were synthesized and tested for cell toxicity, anti-HIV activity, and inhibition of HIV-1 integrase. Seventeen of the 34 analogues had potent activity against HIV-1 integrase ranging from 0.07 to >10 mu M. Seventeen analogues that were synthesized or purchased had no inhibitory activity against integrase at concentrations of 25 mu M. Of the biologically active analogues, 7 of the 17 inhibited HIV replication at nontoxic concentrations. The most potent compounds were D-chicoric acid, meso-chicoric acid, bis(3,4-dihydroxydihydrocinnamoyl)-L-tartaric acid, digalloyl-L-tartaric acid, bis(3,4-dihydroxybenzoyl)-L-tartaric acid, dicaffeoylglyceric acid, and bis(3,4-dihydroxyphenylacetyl)-L-tartaric acid. Anti-HIV activity of the active compounds in tissue culture ranged from 35 to 0.66 mu M. Structure-activity relationships demonstrated that biscatechol moieties were absolutely required for inhibition of integrase, while at least one free carboxyl group was required for anti-HIV activity. These data demonstrate that analogues of the DCTAs and the DCQAs can be synthesized which have improved activity against HIV integrase.
• Fischer; Freundenberg, Chemische Berichte, 1913, vol. 46, p. 1125
  作者：Fischer、Freundenberg

  DOI：——

  日期：——
• Nierenstein, Biochemical Journal, 1915, vol. 9, p. 243
  作者：Nierenstein

  DOI：——

  日期：——
• Fischer,E., Chemische Berichte, 1909, vol. 42, p. 1020
  作者：Fischer,E.

  DOI：——

  日期：——