methyl 2,2,4a,7-tetramethyl-5-(3-methylbut-2-en-1-yl)-2,2a,2a1,3,4,4a,5,6-octahydroindeno[7,1-bc]furan-2a1-carboxylate

• 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 2,2,4a,7-tetramethyl-5-(3-methylbut-2-en-1-yl)-2,2a,2a1,3,4,4a,5,6-octahydroindeno[7,1-bc]furan-2a1-carboxylate
• 英文别名: methyl (4R,7R,8S,11S)-3,3,7,10-tetramethyl-8-(3-methylbut-2-enyl)-2-oxatricyclo[5.3.1.04,11]undec-1(10)-ene-11-carboxylate
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: SCWKPEAIIBVGIZ-AFMUBRCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2,2,4a,7-tetramethyl-5-(3-methylbut-2-en-1-yl)-2,2a,2a1,3,4,4a,5,6-octahydroindeno[7,1-bc]furan-2a1-carboxylate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 以93%的产率得到2,2,4a,7-tetramethyl-5-(3-methylbut-2-en-1-yl)-2,2a,2a1,3,4,4a,5,6-octahydroindeno[7,1-bc]furan-2a1-yl methanol
  参考文献：
  名称：

  Bioinspired Total Synthesis of (±)-Yezo’otogirin C

  摘要：

  The first and protective group-free total synthesis of (+/-)-yezo'otogirin C has been achieved from 3-methyl-4-prenylcyclohex-2-enone in eight steps with 23% overall yield. The tricyclic core of (+/-)-yezo'otogirin C was established via a bioinspired oxidative cascade cyclization strategy using Mn(II)/Mn(III) and O-2, followed by reduction of the peroxy-bridged intermediate using thiourea in refluxing methanol.

  DOI：

  10.1021/ol403374h
• 作为产物：
  描述：

  3-异丁氧基-2-环己烯酮 在 正丁基锂 、 碘 、 manganese (II) acetate tetrahydrate 、 manganese(III) triacetate dihydrate 、 magnesium 、 二异丙胺 、 硫脲 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 62.83h， 生成 methyl 2,2,4a,7-tetramethyl-5-(3-methylbut-2-en-1-yl)-2,2a,2a1,3,4,4a,5,6-octahydroindeno[7,1-bc]furan-2a1-carboxylate
  参考文献：
  名称：

  Systemic Study on the Biogenic Pathways of Yezo’otogirins: Total Synthesis and Antitumor Activities of (±)-Yezo’otogirin C and Its Structural Analogues

  摘要：

  A systematic study of the biomimetic pathways to yezo'otogirin C under aerobic and anaerobic conditions has been investigated, and both are found to be feasible pathways to the natural product depending on the physiological conditions. Because of the lower activation energy, the aerobic process would be more favorable when the in vivo oxygen level is high. In the course of this study, a highly efficient synthetic route to (+/-)-yezo'otogirin C has been established in four steps (31% overall yield) from a readily available compound without using any protecting groups. The natural product and its structural analogues exhibited antitumor activities against several human cancer cell lines and appeared to arrest cell cycles in different phases.

  DOI：

  10.1021/jo502267g