3,5-二羟基-1,7-双(3,4-二羟基苯基)庚烷 | 408324-01-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 中文名称: 3,5-二羟基-1,7-双(3,4-二羟基苯基)庚烷
• 英文名称: (3R,5R)-3,5-dihydroxy-1,7-bis(3,4-dihydroxyphenyl)heptane
• 英文别名: 3,5-Dihydroxy-1,7-bis(3,4-dihydroxyphenyl)heptane；4-[(3R,5R)-7-(3,4-dihydroxyphenyl)-3,5-dihydroxyheptyl]benzene-1,2-diol
• CAS: 408324-01-6
• 化学式: C₁₉H₂₄O₆
• 分子量: 348.396
• InChiKey: DACLCJIHILFMRQ-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  121
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,5-二羟基-1,7-双(3,4-二羟基苯基)庚烷 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 21.0h， 生成 [(3R,5R)-5-(4-bromobenzoyl)oxy-1,7-bis(3,4-dimethoxyphenyl)heptan-3-yl] 4-bromobenzoate
  参考文献：
  名称：

  Tacca chantrieri根茎上的新二芳基庚烷类和二芳基庚烷类苷及其细胞毒活性。

  摘要：

  从番茄根茎中分离出两个新的二芳基庚糖苷（1，2）和七个新的二芳基庚糖苷（3-9）。通过光谱分析确定其结构，包括2D NMR数据和水解裂解结果。通过将CD激子手性方法应用于相应的3,5-双-对-溴苯甲酰基衍生物，确定了新的二芳基庚烷的3,5-二羟基庚烷部分的绝对构型为3R和5R。据报道，分离的化合物和一些衍生物对HL-60人早幼粒细胞白血病细胞，HSC-2人口腔鳞状细胞癌和正常人牙龈成纤维细胞（HGF）的细胞毒活性。

  DOI：

  10.1021/np010470m
• 作为产物：
  描述：

  (3R,5R)-3-acetoxy-5-hydroxy-1,7-bis(3,4-dihydroxyphenyl)heptane 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 3,5-二羟基-1,7-双(3,4-二羟基苯基)庚烷
  参考文献：
  名称：

  Diarylheptanoids from Curcuma kwangsiensis and their inhibitory activity on nitric oxide production in lipopolysaccharide-activated macrophages

  摘要：

  Eleven diarylheptanoids (1-11) were isolated from rhizomes of Curcuma kwangsiensis, together with seven known compounds. Their structures were elucidated by 1D and 2D NMR, circular dichroism (CD), and accurate mass measurements. Inhibitory effects of the isolated compounds on nitric oxide production in lipopolysaccaride-activated macrophages were evaluated. Compounds 1, 2, and 3 showed strong inhibitory activity on NO production with IC50 values of 3.13, 2.81 and 2.41 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.012

文献信息

• Diarylheptanoids from Curcuma kwangsiensis and their inhibitory activity on nitric oxide production in lipopolysaccharide-activated macrophages
  作者：Jun Li、Chun-Ru Liao、Jun-Qi Wei、Li-Xia Chen、Feng Zhao、Feng Qiu

  DOI：10.1016/j.bmcl.2011.07.012

  日期：2011.9

  Eleven diarylheptanoids (1-11) were isolated from rhizomes of Curcuma kwangsiensis, together with seven known compounds. Their structures were elucidated by 1D and 2D NMR, circular dichroism (CD), and accurate mass measurements. Inhibitory effects of the isolated compounds on nitric oxide production in lipopolysaccaride-activated macrophages were evaluated. Compounds 1, 2, and 3 showed strong inhibitory activity on NO production with IC50 values of 3.13, 2.81 and 2.41 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.
• New Diarylheptanoids and Diarylheptanoid Glucosides from the Rhizomes of <i>Tacca chantrieri</i> and Their Cytotoxic Activity
  作者：Akihito Yokosuka、Yoshihiro Mimaki、Hiroshi Sakagami、Yutaka Sashida

  DOI：10.1021/np010470m

  日期：2002.3.1

  Two new diarylheptanoids (1, 2) and seven new diarylheptanoid glucosides (3-9) were isolated from the rhizomes of Tacca chantrieri. Their structures were determined by spectroscopic analysis, including 2D NMR data, and the results of hydrolytic cleavage. The absolute configurations of the 3,5-dihydroxyheptane moieties of the new diarylheptanoids were determined to be 3R and 5R by the application of

  从番茄根茎中分离出两个新的二芳基庚糖苷（1，2）和七个新的二芳基庚糖苷（3-9）。通过光谱分析确定其结构，包括2D NMR数据和水解裂解结果。通过将CD激子手性方法应用于相应的3,5-双-对-溴苯甲酰基衍生物，确定了新的二芳基庚烷的3,5-二羟基庚烷部分的绝对构型为3R和5R。据报道，分离的化合物和一些衍生物对HL-60人早幼粒细胞白血病细胞，HSC-2人口腔鳞状细胞癌和正常人牙龈成纤维细胞（HGF）的细胞毒活性。