(3α,3aβ,8aβ)-octahydro-3-methyl-8-methylenespirodioxolan>-3-ol | 123994-91-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3α,3aβ,8aβ)-octahydro-3-methyl-8-methylenespirodioxolan>-3-ol
• 英文别名: (1'S,3'aR,8'aR)-1'-methyl-4'-methylidenespiro[1,3-dioxolane-2,7'-3,3a,5,6,8,8a-hexahydro-2H-azulene]-1'-ol
• CAS: 123994-91-2
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: FWZBKDUOFWTFQM-XQQFMLRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3α,3aβ,8aβ)-octahydro-3-methyl-8-methylenespirodioxolan>-3-ol 生成 (1S,4R,10R)-1-methyl-5-methylidene-11-oxatricyclo[6.2.1.04,10]undecan-8-ol
  参考文献：
  名称：

  WIJNBERG, JOANNES B. P. A.;DE, GROOT AE., TETRAHEDRON LETT., 28,(1987) N 26, 3007-3010

  摘要：

  DOI：
• 作为产物：
  描述：

  (4aα,5α,8α,8aβ)-octahydro-5,8-dihydroxy-4a,8-dimethyl-2(1H)-naphthalenone 在 lithium carbonate 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 吡啶 、 水 为溶剂， 生成 (3α,3aβ,8aβ)-octahydro-3-methyl-8-methylenespirodioxolan>-3-ol
  参考文献：
  名称：

  选择性碱诱导的全氢萘重排为1,5-顺式稠合的10-亚甲基过氢azulenes

  摘要：

  通过4β羟基化物的分子内辅助，选择性地并且高收率地实现了全氢萘基甲苯磺酸酯3到1，5-顺式10-亚甲基全氢祖烯4的重排。

  DOI：

  10.1016/s0040-4039(00)96269-5

文献信息

• Base-induced and -directed rearrangements of 4-monotosylated perhydronaphthalene-1,4-diols. Synthesis of (.+-.)-5-epi-nardol
  作者：Joannes B. P. A. Wijnberg、Louis H. D. Jenniskens、Gerd A. Brunekreef、Aede De Groot

  DOI：10.1021/jo00290a027

  日期：1990.2
• Rearrangement vs Homofragmentation: Chemical Consequences of Different .sigma.-Relays on the Heterolysis of Sulfonate Esters Induced by Through-Bond Interactions
  作者：Romano V. A. Orru、Joannes B. P. A. Wijnberg、Catharina T. Bouwman、Aede de Groot

  DOI：10.1021/jo00081a016

  日期：1994.1

  An alcoholate function intramolecularly induces heterolysis of a sulfonate ester group in an apolar solvent via orbital interactions through three intervening C-C single bonds (TBI). It is shown that the reactivity of rigid trans-perhydronaphthalene-1,4-diol monosulfonate esters (1-6) upon treatment with sodium tert-amylate in refluxing benzene is only affected by the relative position of the hydroxyl function to the sulfonate ester group and not by the orientation of the hydroxyl group. The two chief pathways by which these compounds react are rearrangement (1, 3, and 4) and homofragmentation (5 and 6). Stereoelectronic effects play a dominant role here, except in compound 2 where steric factors primarily determine the reactivity and product outcome (ether formation). Homofragmentation is much faster than rearrangement and is only possible when a 1,3-bridged through-space interaction accompanies TBI. The extent of TBI as well as the product composition is strongly determined by the sigma-relay of the three C-C bonds between the electron donor (alcoholate) and the electron acceptor (sulfonate ester bond). The results presented here are consistent with the trans rule and show the validity of similar proposals for biosynthetic processes.
• WIJNBERG, JOANNES B. P. A.;JENNISKENS, LOUIS H. D.;BRUNEKREEF, GERD A.;GR+, J. ORG. CHEM., 55,(1990) N, C. 941-948
  作者：WIJNBERG, JOANNES B. P. A.、JENNISKENS, LOUIS H. D.、BRUNEKREEF, GERD A.、GR+

  DOI：——

  日期：——