4,5-Dihydro-4,4,5,5-tetramethyl-3-methylene-(3H)-furan-2-one | 69604-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 4,5-Dihydro-4,4,5,5-tetramethyl-3-methylene-(3H)-furan-2-one
• 英文别名: dihydro-3-methylene-4,4,5,5-tetramethyl-2(3H)-furanone；4,4,5,5-tetramethyl-3-methylene-dihydro-furan-2-one；4,4,5,5-Tetramethyl-3-methylideneoxolan-2-one
• CAS: 69604-12-2
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: RUKRSFLDTGWVGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  2-Bromo-2,3-dimethyl-3-<(2-bromo-1-methoxy-2-propen-1-yl)oxy>butane 在 azobutyronitrile jones reagent 、 potassium tert-butylate 、 三正丁基氢锡 作用下， 以 正戊烷 、 苯 为溶剂， 反应 2.0h， 生成 4,5-Dihydro-4,4,5,5-tetramethyl-3-methylene-(3H)-furan-2-one
  参考文献：
  名称：

  α-亚甲基-γ-丁内酯的前体β-溴丙-2-炔基混合缩醛和溴乙烯双缩二烯丙基混合缩醛的合成新途径

  摘要：

  N-溴代琥珀酰亚胺在甲醇中的β-溴代烯丙基醚（3a - g）或烯丙基烯丙基醚（8d - f）进行卤代反应可得到不饱和卤代化合物（5a - g）或（9d - f），这些化合物通过均相碳环化作用转化为α -亚甲基-γ-丁内酯（7a – g）。

  DOI：

  10.1039/c39880000237

文献信息

• Regio- and stereoselective ring-opening reactions of cyclopropenones: α-methylene-γ-butyrolactones via additions of trichlorocyclopropenylium ions to alkenes
  作者：Klaus Musigmann、Herbert Mayr、Armin de Meijere

  DOI：10.1016/s0040-4039(00)88780-8

  日期：1990.1

  The 2-chloro-3-(2′-chloroalkyl)cyclopropenones 4, readily obtained by hydrolysis of the adducts of the trichlorocyclopropenylium ion onto alkenes, thermally rearrange to propiolic acid chlorides 6. Treatment of 4 with TosOH·H2O in CH2Cl2 yields the (E)-3-chloro-2-(2′-chloroalkyl)acrylic acids 9, which have been converted in two simple steps to α-methylene-γ-butyrolactones 11 with good overall yields

  通过将三氯环丙烯基离子的加合物水解到烯烃上而容易获得的2-氯-3-（2'-氯烷基）环丙烯酮4热重排为丙酰氯6。在CH 2 Cl 2中用TosOH·H 2 O处理4产生（E）-3-氯-2-（2'-氯烷基）丙烯酸9，已通过两个简单步骤将其转化为α-亚甲基-γ -丁内酯11具有良好的总收率。
• Alkylidene lactone synthesis
  作者：Gerald Haaima、Mary-Jeanne Lynch、Anne Routledge、Rex T. Weavers

  DOI：10.1016/s0040-4020(01)87132-5

  日期：1991.1

  The iodoalkylidene lactones formed by reaction of alkenes with acetylenic acids in the presence of N-iodosuccinimide and subsequent free radical cyclisation, can be de-iodinated photochemically or alkylated with lithium diorganocuprate reagents to yield a variety of α-alkylidene lactones.

  在N-碘代琥珀酰亚胺的存在下，烯烃与炔酸反应形成的碘代亚烷基内酯，随后进行自由基环化反应，可以进行光化脱碘或用二有机铜锂试剂进行烷基化，生成各种α-亚烷基内酯。
• De-iodination and isomerisation of iodoalkylidene lactones
  作者：Gerald Haaima、Anne Routledge、Rex T. Weavers

  DOI：10.1016/s0040-4039(01)93474-4

  日期：——

  The (E)-iodoalkylidene lactones which can be formed by reaction of an alkene with N-iodosuccinimide and an acetylenic acid with subsequent free-radical cyclisation, are readily transformed into iodine free alkylidene lactones by photolysis. Under different reaction conditions, the photolyses yield mixtures of (E) and (Z)-iodovinylidene lactones.

  通过烯烃与N-碘代琥珀酰亚胺和炔酸的反应和随后的自由基环化反应可形成的（E）-碘亚烷基内酯易于通过光解转化为不含碘的亚烷基内酯。在不同的反应条件下，光解产生（E）和（Z）-碘亚乙烯基内酯的混合物。
• Hanson, Alfred W.; McCulloch, Archibald W.; McInnes, A. Gavin, Canadian Journal of Chemistry, 1981, vol. 59, p. 288 - 301
  作者：Hanson, Alfred W.、McCulloch, Archibald W.、McInnes, A. Gavin

  DOI：——

  日期：——
• Allenyl ethers as precursors of .alpha.-methylene-.gamma.-butyrolactones and botryodiplodin derivatives
  作者：Jean Pierre Dulcere、Mohamed Naceur Mihoubi、Jean Rodriguez

  DOI：10.1021/jo00073a033

  日期：1993.10

  Beta-Bromopropargyl ethers 2a-h, 11, and 12 or allyl propargyl ethers 8d-h are easily isomerized with potassium tert-butoxide (KO-t-Bu) into the corresponding allenyl derivatives 3a-h, 13, 14, and 9d-h. These compounds afford alpha-methylene-gamma-butyrolactones 7a-h, 25, and 26 by application of the sequence halogenation/dehydrohalogenation/homolytic carbocyclization. Starting from methyl vinyl ketone 1i, similar transformations lead to botryodiplodin (27) or ethoxybotryodiplodin (28).