3,4,6-三甲氧基-1(3H)-异苯并呋喃酮 | 189454-29-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 3,4,6-三甲氧基-1(3H)-异苯并呋喃酮
• 中文别名: 3,4,6-三甲氧基苯酞；,4,6-三甲氧基-1(3H)-异苯并呋喃酮；4,6-三甲氧基-1(3H)-异苯并呋喃酮
• 英文名称: 3,4,6-trimethoxy-3H-isobenzofuran-1-one
• 英文别名: 3,4,6-trimethoxyphthalide；3,5,7-Trimethoxyphthalid；3,4,6-Trimethoxy-1(3H)-isobenzofuranone；3,4,6-trimethoxy-3H-2-benzofuran-1-one
• CAS: 189454-29-3
• 化学式: C₁₁H₁₂O₅
• mdl: MFCD01312574
• 分子量: 224.213
• InChiKey: JNVLFUCEKYADLU-UHFFFAOYSA-N

物化性质

• 熔点：
  149-152 °C (lit.)
• 沸点：
  394.2±42.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  3,4,6-三甲氧基-1(3H)-异苯并呋喃酮 以 水 为溶剂， 反应 0.5h， 以100%的产率得到4,6-dimethoxy-3-hydroxy-(3H)-isobenzofuran-1-one
  参考文献：
  名称：

  Rational design of inhibitors of VirA–VirG two-component signal transduction

  摘要：

  VirA-VirG two-component system regulates the vir (virulence) operon in response to specific host factors (xenognosins) in the plant pathogen Agrobacterium tumefaciens. Using whole cell assays, stable inhibitors inspired by the labile natural benzoxazinone inhibitor HDMBOA are developed. It is found that aromatic aldehydes represent a minimal structural unit for activity. In particular, 3-hydroxy-4,6-dimethoxy-3H-isobenzofuran-1-one (HDI) was found to have the highest activity, making it the most potent developed inhibitor of virulence gene expression in Agrobacterium. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.018
• 作为产物：
  描述：

  3,5-二甲氧基苯甲酸甲酯 在 盐酸 、 四氯化钛 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 3,4,6-三甲氧基-1(3H)-异苯并呋喃酮
  参考文献：
  名称：

  Murty; Hazra; Datta, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 2, p. 126 - 132

  摘要：

  DOI：

文献信息

• Assignment of the Absolute Configuration of<i>Concentricolide</i>- Absolute Configuration Determination of Its Bioactive Analogs Using DFT Methods
  作者：Jie Ren、Ju-Xing Jiang、Liang-Bo Li、Tou-Geng Liao、Ren-Rong Tian、Xu-lin Chen、Si-Ping Jiang、Charles U. Pittman、Hua-Jie Zhu

  DOI：10.1002/ejoc.200900422

  日期：2009.8

  The configuration of concentricolide was assigned as (S). The configuration of its three analogs, which have anti-HIV-1 activity, were predicted by optical rotation values obtained by the B3LYP/aug-cc-pVDZ//B3LYP/6-31+G(d) and B3LYP/aug-cc-pVDZ//MP2/6-311+G(d) methods. The two methods predict very close optical rotation magnitudes for all three chiral analogs of concentricolide. The two methods were

  同心圆的构型被指定为（S）。通过 B3LYP/aug-cc-pVDZ//B3LYP/6-31+G(d) 和 B3LYP/aug-cc 获得的旋光值预测其具有抗 HIV-1 活性的三种类似物的构型-pVDZ//MP2/6-311+G(d) 方法。这两种方法预测同心圆的所有三个手性类似物的旋光度非常接近。这两种方法应用于其他七种同心圆类似物的旋光度预测。在 B3LYP/aug-cc-pVDZ 水平对七个类似物中的四个进行圆二色性计算。((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Rational design of inhibitors of VirA–VirG two-component signal transduction
  作者：Justin Maresh、Jin Zhang、Yih-Ling Tzeng、Nora A. Goodman、David G. Lynn

  DOI：10.1016/j.bmcl.2007.04.018

  日期：2007.6

  VirA-VirG two-component system regulates the vir (virulence) operon in response to specific host factors (xenognosins) in the plant pathogen Agrobacterium tumefaciens. Using whole cell assays, stable inhibitors inspired by the labile natural benzoxazinone inhibitor HDMBOA are developed. It is found that aromatic aldehydes represent a minimal structural unit for activity. In particular, 3-hydroxy-4,6-dimethoxy-3H-isobenzofuran-1-one (HDI) was found to have the highest activity, making it the most potent developed inhibitor of virulence gene expression in Agrobacterium. (c) 2007 Elsevier Ltd. All rights reserved.
• Murty; Hazra; Datta, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 2, p. 126 - 132
  作者：Murty、Hazra、Datta、Mal

  DOI：——

  日期：——

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