| 1603837-06-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• CAS: 1603837-06-4
• 化学式: C₂₄H₃₀O₆
• 分子量: 414.499
• InChiKey: RSKBQUXPZONWFN-CYFREDJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  在 sodium periodate 、 cerium(III) chloride heptahydrate 、 三溴化硼 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 1.33h， 生成 (5aR,9aR,10aS,11aS)-5a-(hydroxymethyl)-8-isopropyl-4,5,5a,10a,11,11a-hexahydro-1H-oxireno[2',3':8a,9]phenanthro[1,2-c]furan-3,9-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of 20-hydroxytriptonide and its analogues

  摘要：

  20-Hydroxytriptonide was synthesized from readily accessible L-abietic acid in 22 linear steps, which features a Barton reaction carried out under air atmosphere to install the C20-hydroxy group. Meanwhile, we also synthesized (5R)-5-hydroxytriptolide's probable metabolite product. Preliminary structure activity relationship studies revealed that C20-angular methyl group might play a key role in maintaining the electronic properties of the whole molecule, which was essential for retaining the cytotoxic activity and might easily and inevitably be affected by the introduction of a new group. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.070
• 作为产物：
  描述：

  20-ethoxymethoxytriptophenolide methylether 在 ammonium cerium (IV) nitrate 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 水 、 乙腈 、 二氯甲烷 为溶剂， 反应 2.0h， 以76%的产率得到
  参考文献：
  名称：

  Synthesis and biological evaluation of 20-hydroxytriptonide and its analogues

  摘要：

  20-Hydroxytriptonide was synthesized from readily accessible L-abietic acid in 22 linear steps, which features a Barton reaction carried out under air atmosphere to install the C20-hydroxy group. Meanwhile, we also synthesized (5R)-5-hydroxytriptolide's probable metabolite product. Preliminary structure activity relationship studies revealed that C20-angular methyl group might play a key role in maintaining the electronic properties of the whole molecule, which was essential for retaining the cytotoxic activity and might easily and inevitably be affected by the introduction of a new group. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.070