(4aR,10aR)-2-[bis(methylsulfanyl)methylidene]-4a-(ethoxymethoxymethyl)-8-methoxy-7-propan-2-yl-4,9,10,10a-tetrahydro-3H-phenanthren-1-one | 1603837-04-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4aR,10aR)-2-[bis(methylsulfanyl)methylidene]-4a-(ethoxymethoxymethyl)-8-methoxy-7-propan-2-yl-4,9,10,10a-tetrahydro-3H-phenanthren-1-one
• CAS: 1603837-04-2
• 化学式: C₂₅H₃₆O₄S₂
• 分子量: 464.69
• InChiKey: RLNGNASLGOGNMY-OFVILXPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  95.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4aR,10aR)-2-[bis(methylsulfanyl)methylidene]-4a-(ethoxymethoxymethyl)-8-methoxy-7-propan-2-yl-4,9,10,10a-tetrahydro-3H-phenanthren-1-one 在 吡啶 、 Oxone 、 sodium periodate 、 正丁基锂 、 ammonium cerium (IV) nitrate 、 1,1,1-三氟丙酮 、 cerium(III) chloride heptahydrate 、 三溴化硼 、 disodium ethylenediaminetetraacetic acid 、 碳酸氢钠 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 18.33h， 生成 20-acetoxytriptonide
  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：

  ((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 、 正丁基锂 、 2,6-二叔丁基-4-甲基苯酚 、 溶剂黄146 、 N,N-二异丙基乙胺 、 锌 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 19.42h， 生成 (4aR,10aR)-2-[bis(methylsulfanyl)methylidene]-4a-(ethoxymethoxymethyl)-8-methoxy-7-propan-2-yl-4,9,10,10a-tetrahydro-3H-phenanthren-1-one
  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

文献信息

• 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.