(Z)-2-(heptadec-10-en-1-yl)-6-methoxybenzene-1,4-diol | 77285-25-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (Z)-2-(heptadec-10-en-1-yl)-6-methoxybenzene-1,4-diol
• 英文别名: 1-(2,5-dihydroxy-3-methoxyphenyl)-10-heptadecene；2-[(Z)-heptadec-10-enyl]-6-methoxybenzene-1,4-diol
• CAS: 77285-25-7
• 化学式: C₂₄H₄₀O₃
• 分子量: 376.58
• InChiKey: BDWQNYPENCTULP-HJWRWDBZSA-N

物化性质

• 沸点：
  515.1±45.0 °C(Predicted)
• 密度：
  0.979±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  27
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-2-(heptadec-10-en-1-yl)-6-methoxybenzene-1,4-diol 在 silver carbonate 作用下， 以 苯 为溶剂， 反应 2.0h， 以94%的产率得到马蔺子素
  参考文献：
  名称：

  A practical preparation of functionalized alkylbenzoquinones: synthesis of maesanin and irisquinone

  摘要：

  DOI：

  10.1021/jo00037a052
• 作为产物：
  描述：

  马蔺子素 在 sodium tetrahydroborate 作用下， 生成 (Z)-2-(heptadec-10-en-1-yl)-6-methoxybenzene-1,4-diol
  参考文献：
  名称：

  鸢尾酮的合成

  摘要：

  首次合成了鸢尾酮，以研究其作为潜在的放射增敏剂的用途。其合成的关键步骤涉及酚醚的区域选择性锂化。顺式-双键已经通过1 H NMR光谱证实。还已经制备了其饱和侧链衍生物和其二氢衍生物。

  DOI：

  10.1016/s0040-4039(01)80507-4

文献信息

• Identification of Novel ROS Inducers: Quinone Derivatives Tethered to Long Hydrocarbon Chains
  作者：Yeonsun Hong、Sandip Sengupta、Wooyoung Hur、Taebo Sim

  DOI：10.1021/jm501846y

  日期：2015.5.14

  We performed the first synthesis of the 17-carbon chain-tethered quinone moiety 22 (SAN5201) of irisferin A, a natural product exhibiting anticancer activity, and its derivatives. We found that 22 is a potent ROS inducer and cytotoxic agent. Compound 25 (SAN7401), the hydroquinone form of 22, induced a significant release of intracellular ROS and apoptosis (EC50 = 1.3-2.6 mu M) in cancer cell lines, including A549 and HCT-116. Compared with the activity of a well-known ROS inducer, piperlongumine, 22 and 25 showed stronger cytotoxicity and higher selectivity over noncancerous cells. Another hydroquinone tethering 12-carbon chain, 26 (SAN4601), generated reduced levels of ROS but showed more potent cytotoxicity (EC50 = 0.8-1.6 mu M) in cancer cells, although it lacked selectivity over noncancerous cells, implying that the naturally occurring 17-carbon chain is also crucial for ROS production and a selective anticancer effect. Both 25 and 26 displayed strong, equipotent activities against vemurafenib-resistant SK-Mel2 melanoma cells and p53-deficient H1299 lung cancer cells as well, demonstrating their broad therapeutic potential as anticancer agents.
• J. Org. Chem. 1992, 57, 3242-3245
  作者：

  DOI：——

  日期：——
• A practical preparation of functionalized alkylbenzoquinones: synthesis of maesanin and irisquinone
  作者：J. S. Yadav、Velaparthi Upender、A. V. Rama Rao

  DOI：10.1021/jo00037a052

  日期：1992.5
• The synthesis of Irisquinone
  作者：Ronald S. Michalak、David R. Myers、Jack L. Parsons、Prabhakar A. Risbood、Rudiger D. Haugwitz、V.L. Narayanan

  DOI：10.1016/s0040-4039(01)80507-4

  日期：1989.1

  Irisquinone has been synthesized for the first time to investigate its use as a potential radiosensitizer. The key step in its synthesis involves the regioselective lithiation of a phenol ether. The cis-double bond has been confirmed via 1H NMR spectroscopy. Its saturated side chain derivative and its dihydro derivative have also been prepared.

  首次合成了鸢尾酮，以研究其作为潜在的放射增敏剂的用途。其合成的关键步骤涉及酚醚的区域选择性锂化。顺式-双键已经通过1 H NMR光谱证实。还已经制备了其饱和侧链衍生物和其二氢衍生物。