(4aS,10aR)-8-methoxy-4a-methyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-one | 1229291-61-5

• 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: (4aS,10aR)-8-methoxy-4a-methyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-one
• CAS: 1229291-61-5
• 化学式: C₁₉H₂₆O₂
• 分子量: 286.414
• InChiKey: DGRCFMHHRWYTCF-QFBILLFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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 、 Jones reagent 、 溶剂黄146 、 亚硝酰氯 、 N,N-二异丙基乙胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 77.92h， 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：

  14-methoxy-19-norabieta-4(18),8,11,13-tetraene 在 臭氧 、 二甲基硫 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以96%的产率得到(4aS,10aR)-8-methoxy-4a-methyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-one
  参考文献：
  名称：

  有效合成关键的中间体雷公藤酚甲醚用于合成（-）-雷公藤内酯

  摘要：

  从九个步骤中容易获得的松香酸3高效合成了雷公藤多酚甲醚4，并已成功应用于（-）-雷公藤内酯1的合成。该路线具有成本低，产量高，易于操作的特点。此外，此路线中的每个反应均已成功扩大规模至100 g底物水平，而没有损失收率。

  DOI：

  10.1016/j.tet.2010.05.035

文献信息

• CN116178479
  申请人：——

  公开号：——

  公开（公告）日：——
• Efficient synthesis of the key intermediate triptophenolide methyl ether for the synthesis of (−)-triptolide
  作者：Bing Zhou、Xiaomei Li、Huijin Feng、Yuanchao Li

  DOI：10.1016/j.tet.2010.05.035

  日期：2010.7

  An efficient synthesis of triptophenolide methyl ether 4 from the readily available abietic acid 3 in nine steps is described and successfully applied to the synthesis of (−)-triptolide 1. The route is of characteristic of low cost, high yield and easy operation. In addition, every reaction in this route has been successfully scaled-up to a 100 g substrate level without loss of yield.

  从九个步骤中容易获得的松香酸3高效合成了雷公藤多酚甲醚4，并已成功应用于（-）-雷公藤内酯1的合成。该路线具有成本低，产量高，易于操作的特点。此外，此路线中的每个反应均已成功扩大规模至100 g底物水平，而没有损失收率。
• Synthesis and biological evaluation of 20-hydroxytriptonide and its analogues
  作者：Hongtao Xu、Huanyu Tang、Zhuo Yang、Huijin Feng、Yuanchao Li

  DOI：10.1016/j.tet.2014.03.070

  日期：2014.5

  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.