(5S,7S)-7-methyl-1,6-dioxaspiro[4.5]decane | 89576-31-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5S,7S)-7-methyl-1,6-dioxaspiro[4.5]decane
• 英文别名: (5R,7S)-7-methyl-1,6-dioxaspiro[4.5]decane
• CAS: 89576-31-8
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: XNNASGSBOJGKAZ-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2(S)-羟基庚-6-烯 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 正丁基锂 、 臭氧 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 40.5h， 生成 (5S,7S)-7-methyl-1,6-dioxaspiro[4.5]decane
  参考文献：
  名称：

  Chemico-enzymatic syntheses of racemic and chiral isomers of 7- methyl-1,6-dioxaspiro[4.5]decane

  摘要：

  Porcine pancreatic lipase (PPL) mediated resolution of 6-heptene-2-ol afforded the enantiomers in high optical purities. Alkylation products of the dianion of the 2-4'-hydroxypentyl-1,3-dithiane prepared from the enantiomers, followed by alkylative hydrolysis, afforded 97% optically pure E-7-methyl-1,6-dioxaspiro[4.5]decane.

  DOI：

  10.1016/s0040-4020(01)86372-9

文献信息

• Fletcher, Mary T.; Wells, Jaqueline A.; Jacobs, Mark F., Journal of the Chemical Society. Perkin transactions I, 1992, # 21, p. 2827 - 2832
  作者：Fletcher, Mary T.、Wells, Jaqueline A.、Jacobs, Mark F.、Krohn, Sabine、Kitching, William、et al.

  DOI：——

  日期：——
• Lipase mediated resolution of 1,3-butanediol derivatives: chiral building blocks for pheromone enantiosynthesis. Part 3
  作者：Isidoro Izquierdo、Marı́a T. Plaza、Miguel Rodrı́guez、Juan A. Tamayo、Alicia Martos

  DOI：10.1016/s0957-4166(01)00038-6

  日期：2001.2

  (R,S)-1,3-butanediol 5 was kinetically resolved by enzymatic acetylation with vinyl acetate under the presence of Chirazyme (TM) L-2, c-f, yielding (S)-1-O-acetyl-1,3-hydroxybutane 6 and (R)-1,3-di-O-acetyl-1,3-butanediol 7 with enantiomeric excesses of 91%, (E=67.3). Compounds 6 and 7 were easily transformed into the corresponding (S)-3-O-(2-methoxyethoxymethyl)-3-hydroxybutanal 10 and (R)-3-benzyloxybutanal 19, through a protection-deprotection and functional group interchange methodology. Subsequent reaction of 10 and 19 with 3-(methoxycarbonlypropionyl-methylene)triphenylphosphorane afforded methyl (E,S)-8-O-(2-methoxyethoxymethyl)-4-oxo-5-nonenoate 12 and (E,R)-8-benzyl-oxy-4-oxo-5-nonenoate 20. The alkenes 19 and 20 were then catalytically hydrogenated to the corresponding saturated eaters 13 and 21. Treatment of 13 and 21 with 1,2-ethanedithiol/F3B . OEt2 afforded dithioketals 14 and 22, which were respectively reduced to (S)-1,8-dihydroxy-4-nonanone ethylidenedithioketal 15 and (R)-8-O-benzyl-1,8-dihydroxy-4-nonanone ethylidenedithioketal 23. Finally, deprotection of 15 by catalytic hydrogenation under acidic conditions gave the expected (5S,7S)-(-)-7-methy1-1,6-dioxaspiro[4.5]decane 1. The (5R,7R)-(+)-1 enantiomer was analogously prepared fi om 23. Both compounds were formed by this procedure with an e.e. of 91%. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Alkynyltrifluoroborates as Versatile Tools in Organic Synthesis:  A New Route to Spiroketals
  作者：Jan Doubský、Ludvík Streinz、David Šaman、Jiří Zedník、Bohumír Koutek

  DOI：10.1021/ol047987k

  日期：2004.12.1

  A simple and efficient two-step approach to spiroketals is described. Key steps include the preparation of functionalized hydroxyl alpha-alkynones by ring-opening reactions of lactones with lithium alkynyltrifluoroborates followed by a palladium-catalyzed hydrogenation/spirocyclization of the prespiroketal intermediate.
• A convenient access to thermodynamically nonstabilised spiroketal isomers: the first synthesis of (Z)-7-methyl-1,6-dioxaspiro[4.5]decane
  作者：Jan Doubský、David Šaman、Jiří Zedník、Soňa Vašíčková、Bohumír Koutek

  DOI：10.1016/j.tetlet.2005.09.085

  日期：2005.11

  Functionalised hydroxy alpha-alkynones were transformed to the corresponding spiroketals by a one-pot cascade consisting of palladium-catalysed hydrogenation of the triple bond, hydroxyl group deprotection and spirocyclisation under mild nonacidic conditions. The reaction does not rely upon thermodynamic control to set the configuration of the ketal stereocentre so that both the anomerically stabilised and nonstabilised isomers are similarly accessible. (c) 2005 Elsevier Ltd. All rights reserved.
• ROSINI, GOFFREDO;BALLINI, ROBERTO;MAROTTA, EMANUELA, TETRAHEDRON, 45,(1989) N8, C. 5935-5942
  作者：ROSINI, GOFFREDO、BALLINI, ROBERTO、MAROTTA, EMANUELA

  DOI：——

  日期：——