1-oxa-4-methylspiro<4.5>dec-3-en-2-one | 4243-31-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 1-oxa-4-methylspiro<4.5>dec-3-en-2-one
• 英文别名: 3-Methyl-4,4-pentamethylene-2-buten-4-olide；4-methyl-5-spiro-1'-cyclohexane-2(5H)-furanone；4-Methyl-1-oxaspiro<4.5>dec-3-en-2-on；3-<1-Hydroxy-cyclohexyl>-crotonsaeure-lacton；4-methyl-1-oxa-spiro[4.5]dec-3-en-2-one；4-Methyl-1-oxaspiro[4.5]dec-3-en-2-one
• CAS: 4243-31-6
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: ULAQFPXPKPWSGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-spiro-1'-cyclohexane-4-methylenedihydro-2-(5H)-furanone 在 双(1,2-双(二苯基膦)乙烷)钯 作用下， 以 苯 为溶剂， 反应 21.0h， 以76%的产率得到1-oxa-4-methylspiro<4.5>dec-3-en-2-one
  参考文献：
  名称：

  TRANSPOSITION OF CO₂GROUP IN 2-FURANONES CATALYZED BY PALLADIUM (0)

  摘要：

  3,3-二烷基-4-亚甲基二氢-2(5H)-呋喃酮 1 异构化为另一种呋喃酮，4-甲基-5,5-二烷基-2(5H)-呋喃酮 2，在催化量的Pd(diphos)2[diphos=Ph2PCH2CH2PPh2]。

  DOI：

  10.1246/cl.1980.1521

文献信息

• Convenient synthesis of 5-alkylidene-2(5H)-furanones,2(5H)-furanones and 2-ethoxyfurans
  作者：R.W. Saalfrank、W. Hafner、J. Markmann、H.-J. Bestmann

  DOI：10.1016/s0040-4020(01)86013-0

  日期：1988.1

  the orthoesters are prepared. can be hydrolyzed under acidic conditions to give 5-alkylidene-2(5H)-furanones . Reaction of 1,2-hydroxyketones and (2,2-diethoxyvinylidene)triphenyl-phosphorane (2) via Michael addition and Wittig reaction yields orthoesters , which can be hydrolyzed to give 2(5H)-furanones and 2-ethoxyfurans respectively.

  从烯化1，2-二酮和（2，2-二乙氧基亚乙烯基）三苯基膦（）或从（2，2-二乙氧基乙烯基）三苯基phenyl四氟硼酸酯（）烯化开始，制备原酸酯。可以在酸性条件下水解，得到5-亚烷基-2（5H）-呋喃酮。1,2-羟基酮与（2,2-二乙氧基亚乙烯基）三苯基-膦烷（2）的反应通过Michael加成反应和Wittig反应生成原酸酯，可以将其水解生成2（5H）-呋喃酮和2-乙氧基呋喃。
• Samarium (II) iodide-induced intermolecular coupling of α,β-unsaturated esters with ketones: reactions of methyl propiolate and ethyl buta-2,3-dienoate with cyclohexanone and its application to synthesis of a terpene carboxylic acid
  作者：Masakazu Sono、Natsuki Doi、Eri Yoshino、Sachiko Onishi、Daiki Fujii、Motoo Tori

  DOI：10.1016/j.tetlet.2013.01.120

  日期：2013.4

  propiolate and ethyl buta-2,3-dienoate with cyclohexanone induced by SmI2 occurred either at α- or β-position to yield different products depending on with or without a proton source. The synthesis of terpenic acid was demonstrated using this reaction.

  SmI 2诱导的丙酸甲酯和2,3-丁二酸丁酸乙酯与环己酮的反应发生在α-位置或β-位置，根据有无质子源产生不同的产物。使用该反应证明了萜烯酸的合成。
• Saalfrank, Rolf W.; Hafner, Wieland; Markmann, Joachim, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1994, vol. 49, # 3, p. 389 - 406
  作者：Saalfrank, Rolf W.、Hafner, Wieland、Markmann, Joachim、Welch, Andreas、Peters, Karl、Schnering, Hans Georg von

  DOI：——

  日期：——
• Unsaturated spiro-γ-lactone formation by the dissociative reduction of bromoacetates
  作者：R.J. Kolt、D. Griller、D.D.M. Wayner

  DOI：10.1016/s0040-4039(00)97292-7

  日期：1990.1

  Unsaturated spiro-gamma-butyrolactones can be prepared in good yields from bromoacetate precursors by a simple route that requires only 2-propanol as solvent and free radical initiation.
• Synthesis of heterospirans containing a γ-lactone ring
  作者：A. A. Avetisyan、G. G. Tokmadzhyan、R. A. Piridzhanyan

  DOI：10.1134/s1070428008070221

  日期：2008.7

  Reactions of alpha-ketols with diethyl malonate at the molar ratio 2:1 in the presence of K(2)CO(3) were investigated. The heterospiranes obtained contained a dihydrofuran and a gamma-lactone rings. The optimum conditions for the synthesis of heterospiranes were found by varying the ratio of the initial compounds: alpha-ketoalcohol (or 2-ethoxycarbonyl-, 2-methoxycarbonyl-, 2-cyano-3,4,4-trimethyl-2-buten-4-olides), diethyl malonate, K(2)CO(3), by varying the environment, and also the temperature and the time of the reaction.