((1S,4aR,10aR)-1-hydroxy-7-isopropyl-8-methoxy-1,2,3,4,4a,9,10,10a-octahydrophenanthren-4a-yl)methyl nitrate | 1603836-98-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: ((1S,4aR,10aR)-1-hydroxy-7-isopropyl-8-methoxy-1,2,3,4,4a,9,10,10a-octahydrophenanthren-4a-yl)methyl nitrate
• 英文别名: [(1S,4aR,10aR)-1-hydroxy-8-methoxy-7-propan-2-yl-2,3,4,9,10,10a-hexahydro-1H-phenanthren-4a-yl]methyl nitrate
• CAS: 1603836-98-1
• 化学式: C₁₉H₂₇NO₅
• 分子量: 349.427
• InChiKey: SZJNEUSFELGHPV-LNLFQRSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ((1S,4aR,10aR)-1-hydroxy-7-isopropyl-8-methoxy-1,2,3,4,4a,9,10,10a-octahydrophenanthren-4a-yl)methyl nitrate 在 Jones reagent 、 溶剂黄146 、 N,N-二异丙基乙胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 5.42h， 生成
  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：

  (4aS,10aR)-8-methoxy-4a-methyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-one 在 吡啶 、 sodium tetrahydroborate 、 亚硝酰氯 作用下， 以 甲醇 为溶剂， 反应 72.5h， 生成 ((1S,4aR,10aR)-1-hydroxy-7-isopropyl-8-methoxy-1,2,3,4,4a,9,10,10a-octahydrophenanthren-4a-yl)methyl nitrate
  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