1-oxaspiro[4.5]decan-3-ol | 29839-61-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 1-oxaspiro[4.5]decan-3-ol
• CAS: 29839-61-0
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: RSNSZCNWYDKPMG-UHFFFAOYSA-N

物化性质

• 沸点：
  240.47°C (rough estimate)
• 密度：
  0.9885 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-oxaspiro[4.5]decan-3-ol 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到1-oxaspiro<4.5>decan-3-one
  参考文献：
  名称：

  General procedure for the synthesis of spirocyclic 3-hydroxy- and 3-oxotetrahydrofurans containing carboand heterocyclic fragments

  摘要：

  Reactions of cyclopentanone, cyclohexanone, N-substituted pyrrolidin-3-one and piperidin-4-one, and tetrahydropyran-4-one with allyl bromide in the presence of zinc and ammonium chloride gave the corresponding geminal hydroxy allyl derivatives. Treatment of the latter with sodium periodate in the presence of sodium metabisulfite resulted in their oxidative cyclization with formation of oxa spirocyclic alcohols containing carbo- and heterocyclic fragments. Swern oxidation of the spiro alcohols afforded the corresponding ketones which were characterized as 2,4-dinitrophenylhydrazones.

  DOI：

  10.1134/s1070428011070207
• 作为产物：
  描述：

  1-oxaspiro<4.5>decan-3-one 在 镍 作用下， 生成 1-oxaspiro[4.5]decan-3-ol
  参考文献：
  名称：

  Colonge; Gaumont, Bulletin de la Societe Chimique de France, 1959, p. 939,941

  摘要：

  DOI：

文献信息

• Transformation of homoallylic alcohol oxides into 3-hydroxytetrahydrofurans in aqueous HClO4
  作者：M. V. Chirskaya、A. A. Vasil’ev、S. V. Shorshnev、S. I. Sviridov

  DOI：10.1007/s11172-006-0415-8

  日期：2006.7

  Hydrolysis of allyl carbinol oxides in aqueous HClO4 gave the corresponding 1,2,4-triols. On heating in the same reaction medium, they underwent cyclization into 3-hydroxytetrahydrofurans. The method is restricted to substrates that can generate stable carbocations via elimination of the hydroxy group from position 4 in intermediate 1,2,4-triols.

  烯丙基甲醇氧化物在 HClO4 水溶液中水解得到相应的 1,2,4-三醇。在相同的反应介质中加热时，它们环化成 3-羟基四氢呋喃。该方法仅限于可通过消除中间体 1,2,4-三醇中 4 位羟基而产生稳定碳正离子的底物。
• New Stereocontrolled Synthesis of Substituted Tetrahydrofurans from 1,3-Dioxolan-4-ones
  作者：Nicos A. Petasis、Shao-Po Lu

  DOI：10.1021/ja00128a044

  日期：1995.6
• Dibutyltin oxide mediated diastereoselective cyclodehydration/sulfonylation of 1,2,4-triols
  作者：Makhosazana P. Gamedze、Comfort M. Nkambule

  DOI：10.1016/j.tetlet.2015.02.083

  日期：2015.4

  Dibutyltin oxide (Bu2SnO) mediated cyclodehydration or sulfonylation of 1,2,4-triols is predictably diastereoselective depending on the steric bulk of the substituents at C4. A larger difference (Delta A-value >1 kcal/mol) leads to the syn-1,2,4-triols favouring cyclodehydration (78-85%) to form 3-hydroxytetrahydrofurans, with the anti-1,2,4-triols favouring monosulfonylation (66-87%). Triols from symmetrical ketones preferentially undergo cyclodehydration in high yield (>75%) due to a gem-disubstituent effect. Thus, the 1,2,4-triols derived from simple cyclic ketones also favour cyclodehydration to form spirocyclic 3-hydroxytetrahydrofurans in 72-79% yields. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of tetrahydrofurans by regio- and stereoselective cyclization of epoxyalcohols using magnesium halide
  作者：Michinori Karikomi、Shigeru Watanabe、Yukino Kimura、Tadao Uyehara

  DOI：10.1016/s0040-4039(02)00042-4

  日期：2002.2

  A Nobel synthetic method for several tetrahydrofuran derivatives by intramolecular cyclization of epoxyalchols is described. The presence of a catalytic amount of magnesium halide altered the regio- and stereoselectivity of the cyclization reaction. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of Propyne(ene)oxy-Substituted Spirotetrahydrofurans
  作者：G. M. Talybov、E. G. Mamedbeyli、F. V. Yusubov

  DOI：10.1134/s1070363218120344

  日期：2018.12

  The intramolecular cycloaddition of homoallyl alcohols to carbocyclic compounds in the presence of molecular and hypervalent iodine leads to the formation of propyne(ene)oxy-substituted spirotetrahydrofurans.