(4-methoxyphenyl)methyl (1R,2S,4R,5R,8R,9S,11R)-9-formyl-2-(hydroxymethyl)-5-methyl-13-propan-2-yltetracyclo[7.4.0.02,11.04,8]tridec-12-ene-1-carboxylate | 205584-10-7

• 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: (4-methoxyphenyl)methyl (1R,2S,4R,5R,8R,9S,11R)-9-formyl-2-(hydroxymethyl)-5-methyl-13-propan-2-yltetracyclo[7.4.0.02,11.04,8]tridec-12-ene-1-carboxylate
• CAS: 205584-10-7
• 化学式: C₂₈H₃₆O₅
• 分子量: 452.591
• InChiKey: KJKZLVZSRIUZRR-MQKLFFJXSA-N

物化性质

• 沸点：
  549.3±50.0 °C(predicted)
• 密度：
  1.227±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4-methoxyphenyl)methyl (1R,2S,4R,5R,8R,9S,11R)-9-formyl-2-(hydroxymethyl)-5-methyl-13-propan-2-yltetracyclo[7.4.0.02,11.04,8]tridec-12-ene-1-carboxylate 在 吡啶 、 盐酸羟胺 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Alkyl side-chain derivatives of sordaricin as potent antifungal agents against yeast

  摘要：

  Sordarin (1) was converted to 5 and 6, which showed potent antifungal activity against yeast. A series of C1-C9 alkyl side-chain derivatives was prepared, from which it was found that the optimal activity occurred with C5. A comparison of side chains with different unsaturation showed that the cis-alkene was the most active. This result suggested that the folding of the side chains might be crucial for the optimal activity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00401-6
• 作为产物：
  描述：

  粪壳菌素 在 盐酸 、 四丁基碘化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 48.0h， 生成 (4-methoxyphenyl)methyl (1R,2S,4R,5R,8R,9S,11R)-9-formyl-2-(hydroxymethyl)-5-methyl-13-propan-2-yltetracyclo[7.4.0.02,11.04,8]tridec-12-ene-1-carboxylate
  参考文献：
  名称：

  索达霉素抗真菌剂。

  摘要：

  通过将有机金属加成到完全保护的苏达霉素醛上来制备基于苏达霉素的化合物。建立了这些化合物的真菌生长抑制曲线，并在此处显示了结果。介绍了合成的索达霉素以及醚和酯衍生物的合成，以及氧化后的结构重排产物。这些化合物被评估为抑制真菌生长的试剂。

  DOI：

  10.1016/s0960-894x(02)00937-x

文献信息

• Sordaricin antifungal agents
  作者：Claude A Quesnelle、Patrice Gill、Marco Dodier、Denis St. Laurent、Michael Serrano-Wu、Anne Marinier、Alain Martel、Charles E Mazzucco、Terry M Stickle、John F Barrett、Dolatrai M Vyas、Balu N Balasubramanian

  DOI：10.1016/s0960-894x(02)00937-x

  日期：2003.2

  organometallic addition onto a fully protected sordaricin aldehyde. The fungal growth inhibition profiles for these compounds were established and the results are presented here. The synthesis of homologated sordaricin as well as ether and ester derivatives is presented, and structural rearrangement products upon oxidation. These compounds were evaluated as agents to inhibit fungal growth.

  通过将有机金属加成到完全保护的苏达霉素醛上来制备基于苏达霉素的化合物。建立了这些化合物的真菌生长抑制曲线，并在此处显示了结果。介绍了合成的索达霉素以及醚和酯衍生物的合成，以及氧化后的结构重排产物。这些化合物被评估为抑制真菌生长的试剂。
• Alkyl side-chain derivatives of sordaricin as potent antifungal agents against yeast
  作者：Bruno Tse、James M. Balkovec、Charles M. Blazey、Ming-Jo Hsu、Jennifer Nielsen、Dennis Schmatz

  DOI：10.1016/s0960-894x(98)00401-6

  日期：1998.8

  Sordarin (1) was converted to 5 and 6, which showed potent antifungal activity against yeast. A series of C1-C9 alkyl side-chain derivatives was prepared, from which it was found that the optimal activity occurred with C5. A comparison of side chains with different unsaturation showed that the cis-alkene was the most active. This result suggested that the folding of the side chains might be crucial for the optimal activity. (C) 1998 Elsevier Science Ltd. All rights reserved.