ovalifoliolatin B

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: ovalifoliolatin B
• 英文别名: 4-Methoxy-2-oxatricyclo[13.2.2.13,7]icosa-1(17),3,5,7(20),8,15,18-heptaen-12-one；4-methoxy-2-oxatricyclo[13.2.2.13,7]icosa-1(17),3,5,7(20),8,15,18-heptaen-12-one
• 化学式: C₂₀H₂₀O₃
• 分子量: 308.377
• InChiKey: QOGTVHQGZNQSJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ovalifoliolatin B 在 10percent Pd/C 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以90%的产率得到4-甲氧基-2-氧杂三环[13.2.2.13,7]二十碳-1(18),3(20),4,6,15(19),16-六烯-12-酮
  参考文献：
  名称：

  Total synthesis of ovalifoliolatin B, acerogenins A and C

  摘要：

  A short and concise route for the synthesis of ovalifoliolatin B, a highly strained macrocyclic diaryl ether heptanoid natural product that also provides quick access to acerogenins A and C natural products has been reported. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.01.135

文献信息

• Synthesis and evaluation of macrocyclic diarylether heptanoid natural products and their analogs
  作者：Vashti C. Bryant、G.D. Kishore Kumar、Abijah M. Nyong、Amarnath Natarajan

  DOI：10.1016/j.bmcl.2011.11.025

  日期：2012.1

  The macrocyclic diarylether heptanoid (MDEH) natural products have been used in folk medicine for centuries. MDEHs are reported to exert anti-tumor properties by inhibiting the activation of NF-kappa B. Here we report the synthesis of a small MDEH library (first reported synthesis of racemic platycarynol) using a Grubbs cross metathesis/Ullmann cyclization strategy. Evaluation of the library led to the identification of MDEH 9b which sensitizes pancreatic cancer cells to gemcitabine mediated growth inhibition and apoptosis. (C) 2011 Elsevier Ltd. All rights reserved.
• Total synthesis of ovalifoliolatin B, acerogenins A and C
  作者：G.D. Kishore Kumar、Amarnath Natarajan

  DOI：10.1016/j.tetlet.2008.01.135

  日期：2008.3

  A short and concise route for the synthesis of ovalifoliolatin B, a highly strained macrocyclic diaryl ether heptanoid natural product that also provides quick access to acerogenins A and C natural products has been reported. (C) 2008 Elsevier Ltd. All rights reserved.