methyl (2S,3aR,3bR,6aS,7aS)-2,3,3a,3b,4,5,6,6a,7,7a-decahydro-2,3b-dimethyl-5-oxo-1H-cyclopentapentalene-2-carboxylate | 97673-19-3

• 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: methyl (2S,3aR,3bR,6aS,7aS)-2,3,3a,3b,4,5,6,6a,7,7a-decahydro-2,3b-dimethyl-5-oxo-1H-cyclopentapentalene-2-carboxylate
• 英文别名: methyl (2S,3aR,3bR,6aS,7aS)-decahydro-2,3b-dimethyl-5-oxo-1H-cyclopenta[a]pentalene-2-carboxylate；methyl (3aR,3bR,5S,6aS,7aS)-3a,5-dimethyl-2-oxo-1,3,3b,4,6,6a,7,7a-octahydrocyclopenta[a]pentalene-5-carboxylate
• CAS: 97673-19-3
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: ULAFNRPHGUHFPS-ZCNHVBTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

上下游信息

反应信息

• 作为反应物：
  描述：

  methyl (2S,3aR,3bR,6aS,7aS)-2,3,3a,3b,4,5,6,6a,7,7a-decahydro-2,3b-dimethyl-5-oxo-1H-cyclopentapentalene-2-carboxylate 在 四氢噻吩 、 palladium diacetate 、 sodium hydroxide 、 sodium tetrahydroborate 、 聚合甲醛 、 aluminum tri-bromide 、 双氧水 、 氧气 、 potassium carbonate 、 palladium dichloride 、 lithium hexamethyldisilazane 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 丙酮 为溶剂， 反应 87.58h， 生成 (1aR-(1aalpha,2beta,3Abeta,3balpha,5alpha,6aalpha,7As*))-十氢-2-羟基-3a,5-二甲基-3-亚甲基-环戊二烯并(4,5)二并环戊烯并(1,6a-b)环氧乙烯-5-羧酸
  参考文献：
  名称：

  An efficient, enantioconvergent total synthesis of natural hirsutic acid C

  摘要：

  DOI：

  10.1021/jo00221a001
• 作为产物：
  描述：

  methyl (2aR,2bR,4S,5aS,6aS)-decahydro-2,2-dichloro-2a,4-dimethyl-1-oxocyclobutapentalene-4-carboxylate 在 溶剂黄146 、 锌 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 4.92h， 生成 methyl (2S,3aR,3bR,6aS,7aS)-2,3,3a,3b,4,5,6,6a,7,7a-decahydro-2,3b-dimethyl-5-oxo-1H-cyclopentapentalene-2-carboxylate
  参考文献：
  名称：

  An efficient, enantioconvergent total synthesis of natural hirsutic acid C

  摘要：

  DOI：

  10.1021/jo00221a001

文献信息

• Iterative three-carbon annelation. A stereoselective total synthesis of (.+-.)-hirsutic acid C
  作者：Andrew E. Greene、Marie Jacqueline Luche、Jean Pierre Depres

  DOI：10.1021/ja00346a054

  日期：1983.4
• Chemoenzymatic total syntheses of the linear triquinane-type natural products (+)-hirsutic acid and (−)-complicatic acid from toluene
  作者：Martin G. Banwell、Kerrie A.B. Austin、Anthony C. Willis

  DOI：10.1016/j.tet.2007.03.073

  日期：2007.7

  Total syntheses of title natural products, 1 and 2, have been achieved using the cis-1,2-dihydrocatechol 7 as starting material. Compound 7 is readily obtained in large quantity and enantiomerically pure form through the whole-cell biotransformation of toluene using the genetically engineered micro-organism Escherichia coli JM109 (pDTG601) that over-expresses the enzyme toluene dioxygenase (TDO). Three key chemical steps were employed in these syntheses, the first of which was a high-pressure- promoted Diels-Alder cycloaddition reaction between diene 8 and cyclopentenone to give adduct 9. The second key step was the photochemically promoted oxa-di-pi-methane rearrangement of the bicyclo[2.2.2] octenone derivative, 18, of 9 to give 20 while the third key step was the reductive cleavage of the last compound so as to afford the linear triquinane 22. Elaboration of compound 22 to targets 1 and 2 followed conventional and/or established procedures. Single-crystal X-ray analyses were carried out on compounds 10-13, 15, 18, 24, and 34. (c) 2007 Elsevier Ltd. All rights reserved.
• An efficient, enantioconvergent total synthesis of natural hirsutic acid C
  作者：Andrew E. Greene、Marie Jacqueline Luche、A. Aarao Serra

  DOI：10.1021/jo00221a001

  日期：1985.10