methyl 2-[(1'S,4'aS,8'aS)-1',4'a-dimethyl-2'-oxospiro[1,3-dioxolane-2,5'-3,4,6,7,8,8a-hexahydronaphthalene]-1'-yl]acetate | 218453-53-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 2-[(1'S,4'aS,8'aS)-1',4'a-dimethyl-2'-oxospiro[1,3-dioxolane-2,5'-3,4,6,7,8,8a-hexahydronaphthalene]-1'-yl]acetate
• CAS: 218453-53-3
• 化学式: C₁₇H₂₆O₅
• 分子量: 310.39
• InChiKey: PBUAHEZQKPANRU-RCBQFDQVSA-N

物化性质

• 沸点：
  406.1±45.0 °C(predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-[(1'S,4'aS,8'aS)-1',4'a-dimethyl-2'-oxospiro[1,3-dioxolane-2,5'-3,4,6,7,8,8a-hexahydronaphthalene]-1'-yl]acetate 在 对甲苯磺酸 、 铱 正丁基锂 、 硫酸 、 氢气 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 苯 为溶剂， 生成 2-[(1R,2R,4aS,8aS)-5-(1,3-dithian-2-yl)-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]acetaldehyde
  参考文献：
  名称：

  Towards the total synthesis of clerocidin. Efficient assembly of the decalin subunit

  摘要：

  Decalin 14, the fully-functionalised southern subunit of Clerocidin 1, a unique fungal metabolite, can be readily and stereoselectively assembled from diketone 7. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01048-5
• 作为产物：
  描述：

  (S)-5,8alpha-二甲基-3,4,8,8alpha-四氢-2H,7H-萘-1,6-二酮 在 氨 、 草酸 、 lithium 作用下， 生成 methyl 2-[(1'S,4'aS,8'aS)-1',4'a-dimethyl-2'-oxospiro[1,3-dioxolane-2,5'-3,4,6,7,8,8a-hexahydronaphthalene]-1'-yl]acetate
  参考文献：
  名称：

  An investigation into the total synthesis of clerocidin: stereoselective synthesis of a clerodane intermediate

  摘要：

  A key clerodane intermediate was prepared during the investigation of the total synthesis of clerocidin. The diterpene backbone was synthesized by an enantioselective Robinson annulation followed by trapping of the enolate using allyl bromide. Selective hydrogenation conditions were developed to introduce the axial methyl group at the C-8 position. A palladium-mediated carbonylation reaction was employed to generate the key alpha,beta-unsaturated dialdehyde. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00349-8

文献信息

• An investigation into the total synthesis of clerocidin: stereoselective synthesis of a clerodane intermediate
  作者：Ji-In Kim Almstead、Thomas P. Demuth、Benoit Ledoussal

  DOI：10.1016/s0957-4166(98)00349-8

  日期：1998.9

  A key clerodane intermediate was prepared during the investigation of the total synthesis of clerocidin. The diterpene backbone was synthesized by an enantioselective Robinson annulation followed by trapping of the enolate using allyl bromide. Selective hydrogenation conditions were developed to introduce the axial methyl group at the C-8 position. A palladium-mediated carbonylation reaction was employed to generate the key alpha,beta-unsaturated dialdehyde. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Towards the total synthesis of clerocidin. Efficient assembly of the decalin subunit
  作者：István E Markó、Marianne Wiaux、Stuart M Warriner、Paul R Giles、Paul Eustace、David Dean、Marc Bailey

  DOI：10.1016/s0040-4039(99)01048-5

  日期：1999.7

  Decalin 14, the fully-functionalised southern subunit of Clerocidin 1, a unique fungal metabolite, can be readily and stereoselectively assembled from diketone 7. (C) 1999 Elsevier Science Ltd. All rights reserved.