(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 | 1603837-09-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (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
• CAS: 1603837-09-7
• 化学式: C₂₀H₂₂O₅
• 分子量: 342.392
• InChiKey: ADLBZFNVKZITFT-QTLCSOKXSA-N

物化性质

• 沸点：
  621.1±55.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  76.13
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (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 在 selenium(IV) oxide 、 Oxone 、 1,1,1-三氟丙酮 、 disodium ethylenediaminetetraacetic acid 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 17.0h， 生成 (5R)-5,20-dihydroxytriptonide
  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 sodium periodate 、 ammonium cerium (IV) nitrate 、 cerium(III) chloride heptahydrate 、 三溴化硼 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.33h， 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