3',4',4'a,7',8',8'a-hexahydro-5'-(2-oxoethyl)-8'a-methylspiro<1,3-dioxolane-2,1'(2'H)-naphthalen>-6'(5'H)-one | 137006-96-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3',4',4'a,7',8',8'a-hexahydro-5'-(2-oxoethyl)-8'a-methylspiro<1,3-dioxolane-2,1'(2'H)-naphthalen>-6'(5'H)-one
• 英文别名: 2-[(4'aR,8'aR)-4'a-methyl-2'-oxospiro[1,3-dioxolane-2,5'-3,4,6,7,8,8a-hexahydro-1H-naphthalene]-1'-yl]acetaldehyde
• CAS: 137006-96-3
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: HVIKUVUXSBBVRC-JWCMVYSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 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：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3',4',4'a,7',8',8'a-hexahydro-5'-(2-oxoethyl)-8'a-methylspiro<1,3-dioxolane-2,1'(2'H)-naphthalen>-6'(5'H)-one 在 乙酸酐 作用下， 以 溶剂黄146 为溶剂， 反应 1.5h， 生成 4,5,5a,8,9,9a-hexahydro-5a-methyl-6(7H)-oxonaphtho<2,1-b>furan-2-carboxaldehyde
  参考文献：
  名称：

  Synthetic studies towards paspalicine: Preliminary investigations, and the synthesis of 3′,4′,7′,7′a,9′,10′,11′,11′a-octahydro-4′,4′,7′a-trimethylspiro[1,3-dioxolane]-2,8′(6′H)-2′H-3′,5′a-epoxynaphth [2,1-b]oxepin-2′-one

  摘要：

  Preliminary investigations directed towards the synthesis of the indole-diterpene mould metabolite, paspalicine 1, are described. Following the preparation of the beta-pyrone ketal 7, which contains the characteristic functional group of paspalicine, the compound 25, which constitutes rings D-G of paspalicine with the correct relative stereochemistry, has been synthesised in eight steps from the monoketal 12 of the Wieland-Miescher ketone, in an overall yield of 8%.

  DOI：

  10.1016/s0040-4020(01)86569-8
• 作为产物：
  描述：

  3',4',8',8'a-tetrahydro-8'a-methylspiro[1,3-dioxolane-2,1'(2'H)-naphthalen]-6'(7'H)-one 在 氨 、 水 、 lithium 、 臭氧 、 三苯基膦 作用下， 反应 1.17h， 生成 3',4',4'a,7',8',8'a-hexahydro-5'-(2-oxoethyl)-8'a-methylspiro<1,3-dioxolane-2,1'(2'H)-naphthalen>-6'(5'H)-one
  参考文献：
  名称：

  Synthetic studies towards paspalicine: Preliminary investigations, and the synthesis of 3′,4′,7′,7′a,9′,10′,11′,11′a-octahydro-4′,4′,7′a-trimethylspiro[1,3-dioxolane]-2,8′(6′H)-2′H-3′,5′a-epoxynaphth [2,1-b]oxepin-2′-one

  摘要：

  Preliminary investigations directed towards the synthesis of the indole-diterpene mould metabolite, paspalicine 1, are described. Following the preparation of the beta-pyrone ketal 7, which contains the characteristic functional group of paspalicine, the compound 25, which constitutes rings D-G of paspalicine with the correct relative stereochemistry, has been synthesised in eight steps from the monoketal 12 of the Wieland-Miescher ketone, in an overall yield of 8%.

  DOI：

  10.1016/s0040-4020(01)86569-8

文献信息

• ALI, AMIN;GUILE, SIMON D.;SAXTON, J. EDWIN;THORNTON-PETT, MARK, TETRAHEDRON, 47,(1991) N2, C. 6407-6426
  作者：ALI, AMIN、GUILE, SIMON D.、SAXTON, J. EDWIN、THORNTON-PETT, MARK

  DOI：——

  日期：——