(E)-2-Methyl-1,7-dioxaspiro<5.6>dodecane | 80607-87-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (E)-2-Methyl-1,7-dioxaspiro<5.6>dodecane
• 英文别名: 2-methyl-1,7-dioxaspiro[5.6]dodecane；(2R,6S)-2-methyl-1,12-dioxaspiro[5.6]dodecane
• CAS: 80607-87-0；105343-06-4；132072-72-1；146389-18-6
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: WLQFFPNTGKKCAI-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 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：

  在 Amberlite IR 120 、 potassium diisopropylamide 、 magnesium sulfate 作用下， 以 四氢呋喃 为溶剂， 反应 49.5h， 生成 (E)-2-Methyl-1,7-dioxaspiro<5.6>dodecane
  参考文献：
  名称：

  Synthesis of Spiroacetal Pheromones via Metalated Hydrazones

  摘要：

  通过合适的亲电试剂与金属化丙酮二甲基脲的α,α′-烷基化反应，随后进行酸催化的断裂和环化闭合，描述了简单烷基取代螺缩醛的合成方法。

  DOI：

  10.1055/s-1990-27080

文献信息

• Mori, Kenji; Katsurada, Manabu, Liebigs Annalen der Chemie, 1984, # 1, p. 157 - 161
  作者：Mori, Kenji、Katsurada, Manabu

  DOI：——

  日期：——
• 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.
• S-(+)-5-(Phenylthio)-2-pentanol and S-(+)-4-(Phenylthio)-2-butanol: Readily Prepared, Useful Additions to the Chirality Pool. Highly Enantioselective Syntheses of Naturally Occurring Spiroketal Pheromones
  作者：Hong Liu、Theodore Cohen

  DOI：10.1021/jo00112a025

  日期：1995.4

  The new chirons (S)-4-(phenylthio)-2-butanol (4) and (S)-5-(phenylthio)-2-pentanol (3) have been prepared efficiently in high enantiomeric excess by enzymatic reduction of the corresponding readily available ketones. Using the latter as a chiral building block, the highly optically enriched insect pheromonal components (5S,7S)-7-methyl-1,6-dioxaspiro[4.5]decane (7), (2S,6R)-2-methyl-1,7-dioxaspiro[5.5]undecane (8), and (2S,6R)-2-methyl-1,7-dioxaspiro[5.6]dodecane (9) have been synthesized in one pot by sequential deprotonation, reductive lithiation, transmetalation with cerium(III) chloride, treatment with lactones, and acidification.
• Ballini, Roberto; Petrini, Marino, Journal of the Chemical Society. Perkin transactions I, 1992, # 23, p. 3159 - 3160
  作者：Ballini, Roberto、Petrini, Marino

  DOI：——

  日期：——
• Synthesis of Spiroacetal Pheromones via Metalated Hydrazones
  作者：Dieter Enders、Walter Dahmen、Eleonore Dederichs、Winfried Gatzweiler、Peter Weuster

  DOI：10.1055/s-1990-27080

  日期：——

  The synthesis of simple alkyl substituted spiroacetals by α,α′-alkylation of metalated acetone dimethylhydrazone with appropriate electrophiles and subsequent acid catalyzed cleavage and ring closure of the products is described.

  通过合适的亲电试剂与金属化丙酮二甲基脲的α,α′-烷基化反应，随后进行酸催化的断裂和环化闭合，描述了简单烷基取代螺缩醛的合成方法。