(2R,3aS,4S,5S,5aS,8aR,11aR,11bS,11cS)-2,3a,6,6,10,10,11c-Heptamethyl-2-vinyl-dodecahydro-3,9,11-trioxa-cyclohepta[def]phenanthrene-4,5-diol | 126749-65-3

• 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: (2R,3aS,4S,5S,5aS,8aR,11aR,11bS,11cS)-2,3a,6,6,10,10,11c-Heptamethyl-2-vinyl-dodecahydro-3,9,11-trioxa-cyclohepta[def]phenanthrene-4,5-diol
• 英文别名: (1R,5R,7R,9S,10S,11S,12S,16S,17S)-7-ethenyl-3,3,7,9,13,13,16-heptamethyl-2,4,8-trioxatetracyclo[7.6.2.05,17.012,16]heptadecane-10,11-diol
• CAS: 126749-65-3
• 化学式: C₂₃H₃₈O₅
• 分子量: 394.552
• InChiKey: NYQBFZJIZNTSAH-SOUPCIKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3aS,4S,5S,5aS,8aR,11aR,11bS,11cS)-2,3a,6,6,10,10,11c-Heptamethyl-2-vinyl-dodecahydro-3,9,11-trioxa-cyclohepta[def]phenanthrene-4,5-diol 在 4-二甲氨基吡啶 、 sodium hydroxide 作用下， 以 吡啶 、 水 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Structures of five new highly oxygenated labdane-type diterpenoids, ptychantins A-E, closely related to forskolin from the liverwort Ptychanthus striatus

  摘要：

  Five novel labdane-type diterpenoids, named ptychantins A-E, closely related to forskolin have been isolated from the liverwort Ptychanthus striatus, and their absolute structures established by a combination of high resolution NMR and CD spectra, X-ray crystallographic analysis and chemical degradation.

  DOI：

  10.1016/s0040-4039(00)73524-6
• 作为产物：
  描述：

  Acetic acid (1R,3R,4aS,5S,6S,6aS,7R,10R,10aS,10bS)-6,10-diacetoxy-5-hydroxy-3,4a,7,10a-tetramethyl-7-(toluene-4-sulfonyloxymethyl)-3-vinyl-dodecahydro-benzo[f]chromen-1-yl ester 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 乙醚 为溶剂， 生成 (2R,3aS,4S,5S,5aS,8aR,11aR,11bS,11cS)-2,3a,6,6,10,10,11c-Heptamethyl-2-vinyl-dodecahydro-3,9,11-trioxa-cyclohepta[def]phenanthrene-4,5-diol
  参考文献：
  名称：

  Structures of five new highly oxygenated labdane-type diterpenoids, ptychantins A-E, closely related to forskolin from the liverwort Ptychanthus striatus

  摘要：

  Five novel labdane-type diterpenoids, named ptychantins A-E, closely related to forskolin have been isolated from the liverwort Ptychanthus striatus, and their absolute structures established by a combination of high resolution NMR and CD spectra, X-ray crystallographic analysis and chemical degradation.

  DOI：

  10.1016/s0040-4039(00)73524-6

文献信息

• Expedient Synthetic Transformation of Ptychantins into Forskolin
  作者：Hisahiro Hagiwara、Masashi Tsukagoshi、Takashi Hoshi、Toshio Suzuki、Toshihiro Hashimoto、Yoshinori Asakawa

  DOI：10.1055/s-2008-1042930

  日期：2008.4

  Forskolin has been synthesized in 11 steps with a 17% overall yield from ptychantins A and B, which have been isolated from the liverwort PTYCHANTHUS STRIATUS in good yield. The 1α-hydroxy group was furnished by stereoselective reduction of the corresponding carbonyl group by sodium cyanoborohydride. The 9α-hydroxy group was introduced stereoselectively by epoxidation of Δ 9,11 -enol ether.

  Forskolin 是通过 11 个步骤从 PTyCHANTins A 和 B 中合成的，总产率为 17%，这些 PTyCHANTins A 和 B 已经以良好的产率从地衣 PTYCHANTHUS STRIATUS 中分离出来。1α-羟基通过氰基硼氢化钠立体选择性还原相应的羰基得到。9α-羟基通过Δ 9,11-烯醇醚的环氧化立体选择性地引入。