2-Methoxy-2-methyldihydro-3(2H)-furanone | 165127-45-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Methoxy-2-methyldihydro-3(2H)-furanone
• 英文别名: laurencione methyl ester；2-Methoxy-2-methyldihydrofuran-3(2 h)-one；2-methoxy-2-methyloxolan-3-one
• CAS: 165127-45-7
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: XQOCDLCNFIWLJQ-UHFFFAOYSA-N

物化性质

• 沸点：
  183.4±40.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Methoxy-2-methyldihydro-3(2H)-furanone 在 对甲苯磺酸 作用下， 以 水 、 苯 为溶剂， 反应 1.0h， 生成 2-甲基-3(2H)-呋喃酮
  参考文献：
  名称：

  Synthesis of Laurencione, a Labile Dihydro-3(2H)-furanone Derivative from the Red Alga Laurencia spectabilis

  摘要：

  The first total synthesis of laurencione, a naturally occurring dihydro-3(2H-furanone derivative isolated from the red alga Laurencia spectabilis, is described. The synthesis is comprised (1) of conversion of gamma-butyrolactone into alpha,alpha-dimethoxy-gamma-butyrolactone, (2) addition of methyllithium across the lactone carbonyl, and (3) acid hydrolysis of the acetal moiety. An alternative synthesis consists of the acid-catalyzed conversion of 3,3-dimethoxy-2-hydroxy-2-methyltetrahydrofuran into laurencione methyl ether and subsequent acid-catalyzed hydrolysis. In addition, a convenient synthesis of the coffee and caramel flavor component 2-methyl-3(2H)-furanone has been developed by acid-catalyzed rearrangement of 2-methoxy-2-methyltetrahydrofuran-3-one.

  DOI：

  10.1021/jo00121a051
• 作为产物：
  描述：

  [2,2-Dichloro-1-methyl-4-trimethylsilanyloxy-but-(E)-ylidene]-isopropyl-amine 在 盐酸 、 sodium methylate 作用下， 生成 2-Methoxy-2-methyldihydro-3(2H)-furanone
  参考文献：
  名称：

  New Formal Syntheses of Laurencione, a Labile Dihydrofuranone Derivative from the Red Alga Laurencia spectabilis

  摘要：

  以 5-乙酰氧基-3-氯戊-2-酮为起始化合物，开发了一种海洋天然产物月桂酮的直接正规合成方法。合成路线包括：(i) δ±-亚硫酰化；(ii) δ-氧硫化物的δ±-氯化；(iii) Hg2+ 催化的甲醇分解；(iv) δ-乙酰氧基-δ±,δ-二甲氧基酮的甲醇分解及随后的环化；(v) 缩醛的酸水解。另一种方法是通过一系列反应从 1,1-二氯丙酮制备月桂二酮，这些反应包括：(i) 亚氨基化；(ii) 区域特异性δ-²-羟乙基化；(iii) 水解；(iv) 碱诱导生成的官能化四氢呋喃的重排；(v) 月桂二酮甲醚的最终酸水解。

  DOI：

  10.1055/s-1996-4335

文献信息

• New Formal Syntheses of Laurencione, a Labile Dihydrofuranone Derivative from the Red Alga Laurencia spectabilis
  作者：Norbert De Kimpe、Angelina Georgieva、Marc Boeykens、Ivan Kozekov、Wim Aelterman

  DOI：10.1055/s-1996-4335

  日期：1996.9

  A straightforward formal synthesis of the marine natural products laurencione was developed, utilizing elaboration of 5-acetoxy-3-chloropentan-2-one as the starting compound. The synthetic route consisted of (i) α-sulfenylation, (ii) α-chlorination of the resulting β-oxo sulfide, (iii) Hg2+-catalyzed methanolysis, (iv) methanolysis of the γ-acetoxy-α,α-dimethoxy ketone with subsequent cyclization and (v) acid hydrolysis of the acetal. Alternatively, laurencione was prepared from 1,1-dichloroacetone by a sequence of reactions involving (i) imination, (ii) regiospecific β-hydroxyethylation, (iii) hydrolysis, (iv) base-induced rearrangement of the resulting functionalized tetrahydrofuran and (v) final acid hydrolysis of laurencione methyl ether.

  以 5-乙酰氧基-3-氯戊-2-酮为起始化合物，开发了一种海洋天然产物月桂酮的直接正规合成方法。合成路线包括：(i) δ±-亚硫酰化；(ii) δ-氧硫化物的δ±-氯化；(iii) Hg2+ 催化的甲醇分解；(iv) δ-乙酰氧基-δ±,δ-二甲氧基酮的甲醇分解及随后的环化；(v) 缩醛的酸水解。另一种方法是通过一系列反应从 1,1-二氯丙酮制备月桂二酮，这些反应包括：(i) 亚氨基化；(ii) 区域特异性δ-²-羟乙基化；(iii) 水解；(iv) 碱诱导生成的官能化四氢呋喃的重排；(v) 月桂二酮甲醚的最终酸水解。
• Synthesis of Laurencione, a Labile Dihydro-3(2H)-furanone Derivative from the Red Alga Laurencia spectabilis
  作者：Norbert De Kimpe、Angelina Georgieva、Marc Boeykens、Laszlo Lazar

  DOI：10.1021/jo00121a051

  日期：1995.8

  The first total synthesis of laurencione, a naturally occurring dihydro-3(2H-furanone derivative isolated from the red alga Laurencia spectabilis, is described. The synthesis is comprised (1) of conversion of gamma-butyrolactone into alpha,alpha-dimethoxy-gamma-butyrolactone, (2) addition of methyllithium across the lactone carbonyl, and (3) acid hydrolysis of the acetal moiety. An alternative synthesis consists of the acid-catalyzed conversion of 3,3-dimethoxy-2-hydroxy-2-methyltetrahydrofuran into laurencione methyl ether and subsequent acid-catalyzed hydrolysis. In addition, a convenient synthesis of the coffee and caramel flavor component 2-methyl-3(2H)-furanone has been developed by acid-catalyzed rearrangement of 2-methoxy-2-methyltetrahydrofuran-3-one.