rac-3-oxodiplophyllin | 56393-93-2

• 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: rac-3-oxodiplophyllin
• 英文别名: dl-3-Oxodiplophyllin；3-oxoalloalantolactone；(3aR,8aR,9aR)-5,8a-dimethyl-3-methylene-3a,4,7,8,9,9a-hexahydrobenzo[f]benzofuran-2,6-dione；(3aR,8aR,9aR)-5,8a-dimethyl-3-methylidene-3a,4,7,8,9,9a-hexahydrobenzo[f][1]benzofuran-2,6-dione
• CAS: 56393-93-2
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: BPLQJGDRWSHVJJ-WDBKCZKBSA-N

物化性质

• 沸点：
  437.8±45.0 °C(predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  rac-3-oxodiplophyllin 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 以81%的产率得到3,4-二硝基氯苯
  参考文献：
  名称：

  Synthesis of yomogin using a telescoped α-methylene-γ-butyrolactone annelation procedure

  摘要：

  A novel and efficient synthetic route to the anti-cancer natural product yomogin has been developed using a Telescoped Intramolecular Michael-Olefination (TIMO) sequence as the key step. Two variants of the TIMO sequence have been used successfully: a two-step acylation approach using diethyl phosphonoacetic acid and a base-free variant using triphenylphosphoranylideneketene (Bestmann's ylide). The natural product, 3-oxodiplophyllin, was also prepared en route to yomogin. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.143
• 作为产物：
  描述：

  6-[3-[Tert-butyl(dimethyl)silyl]oxypentyl]-4-hydroxy-6-methylcyclohex-2-en-1-one 在 氢氟酸 、 戴斯-马丁氧化剂 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 生成 rac-3-oxodiplophyllin
  参考文献：
  名称：

  Synthesis of yomogin using a telescoped α-methylene-γ-butyrolactone annelation procedure

  摘要：

  A novel and efficient synthetic route to the anti-cancer natural product yomogin has been developed using a Telescoped Intramolecular Michael-Olefination (TIMO) sequence as the key step. Two variants of the TIMO sequence have been used successfully: a two-step acylation approach using diethyl phosphonoacetic acid and a base-free variant using triphenylphosphoranylideneketene (Bestmann's ylide). The natural product, 3-oxodiplophyllin, was also prepared en route to yomogin. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.143

文献信息

• Eudesman-12,8β-olides and other terpenes from Artemisia species
  作者：Harald Greger、Christa Zdero、Ferdinand Bohlmann

  DOI：10.1016/0031-9422(86)80022-x

  日期：——

  already known terpenes, eleven new cudesmanolides whereas four new guaianolides were found in A. gmelinii. No sesquiterpene lactones were detected in the aerial parts of A. santolinifolia which afforded two new nerolidol derivatives besides several other already known compounds. From A. caerulescens var. cretacea six eudesmanolides were isolated, one of which has not been reported previously. The structures

  摘要 Artemisia iwayomogi 的地上部分除了已知的萜烯外，还提供了 11 种新的 cudesmanolides，而在 A. gmelinii 中发现了 4 种新的愈创木酚内酯。在 A. santolinifolia 的地上部分未检测到倍半萜内酯，除了几种其他已知化合物外，这还提供了两种新的橙花醇衍生物。来自 A. caerulescens var。白垩纪中分离出六种eudesmanolides，其中一种以前没有报道过。通过高场1H NMR光谱和化学转化阐明了结构。简要讨论了 Abrotanum 和 Seriphidium 亚属中倍半萜内酯的化学分类学意义。
• Laatsch, Hartmut, Liebigs Annalen der Chemie, 1986, # 5, p. 839 - 858
  作者：Laatsch, Hartmut

  DOI：——

  日期：——
• Total synthesis of dl-3-oxodiplophyllin and dl-yomogin
  作者：Drury Caine、Gerard Hasenhuettl

  DOI：10.1021/jo01304a027

  日期：1980.8
• MARCO, J. ALBERTO;CARDA, MIGUEL, TETRAHEDRON, 43,(1987) N 11, 2523-2532
  作者：MARCO, J. ALBERTO、CARDA, MIGUEL

  DOI：——

  日期：——
• Synthesis of umbellifolide and three natural eudesman-12,8-olides from (-)-artemisin
  作者：J. Alberto Marco、Miguel Carda

  DOI：10.1016/s0040-4020(01)81659-8

  日期：——