ethyl 4,4-diethoxy-1-[(3aS,5S,7aS)-(3a-hydroxy-7a-methyl-1-oxoperhydroinden-5-yl)]cyclohexanecarboxylate | 500758-08-7

• 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: ethyl 4,4-diethoxy-1-[(3aS,5S,7aS)-(3a-hydroxy-7a-methyl-1-oxoperhydroinden-5-yl)]cyclohexanecarboxylate
• 英文别名: ethyl 1-[(3aS,5S,7aS)-3a-hydroxy-7a-methyl-1-oxo-2,3,4,5,6,7-hexahydroinden-5-yl]-4,4-diethoxycyclohexane-1-carboxylate
• CAS: 500758-08-7
• 化学式: C₂₃H₃₈O₆
• 分子量: 410.551
• InChiKey: SHTONDPJMDQNFF-WEYGHZABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 4,4-diethoxy-1-[(3aS,5S,7aS)-(3a-hydroxy-7a-methyl-1-oxoperhydroinden-5-yl)]cyclohexanecarboxylate 在 吡啶 、 lithium aluminium tetrahydride 、 4 A molecular sieve 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 (3aS,5S,7aS)-5-[(1-tert-butyldimethylsiloxymethyl-4-oxo)cyclohexyl]-3a-hydroxy-7a-methylperhydroinden-1-one
  参考文献：
  名称：

  Synthesis of B,B-dinor-B-secosteroids as potential cardenolide analogues

  摘要：

  A novel chemical construction of B,B-dinor-B-secosteroids as simplified cardenolide analogs, starting from the Hajos-Parrish diketone was developed. The synthesis of the equivalent of the steroid A ring was carried out through a Diels-Alder reaction between an appropriate hydroindenyl acrylate derivative and Danishefsky's diene. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01361-3
• 作为产物：
  描述：

  乙醇 、 ethyl 1-[(3aS,5S,7aS)-(3a-hydroxy-7a-methyl-1-oxoperhydroinden-5-yl)]-4-oxocyclohex-2-enecarboxylate 在 palladium on activated charcoal 氢气 作用下， 20.0 ℃ 、202.65 kPa 条件下， 以82%的产率得到ethyl 4,4-diethoxy-1-[(3aS,5S,7aS)-(3a-hydroxy-7a-methyl-1-oxoperhydroinden-5-yl)]cyclohexanecarboxylate
  参考文献：
  名称：

  Synthesis of B,B-dinor-B-secosteroids as potential cardenolide analogues

  摘要：

  A novel chemical construction of B,B-dinor-B-secosteroids as simplified cardenolide analogs, starting from the Hajos-Parrish diketone was developed. The synthesis of the equivalent of the steroid A ring was carried out through a Diels-Alder reaction between an appropriate hydroindenyl acrylate derivative and Danishefsky's diene. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01361-3