(+/-)-2-Hydroxy-2-methyldihydrofuran-3(2H)-one | 148159-54-0

• 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: (+/-)-2-Hydroxy-2-methyldihydrofuran-3(2H)-one
• 英文别名: 2-hydroxy-2-methyloxolan-3-one
• CAS: 148159-54-0
• 化学式: C₅H₈O₃
• 分子量: 116.117
• InChiKey: SDZFQGFPZSKQIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-2-Hydroxy-2-methyldihydrofuran-3(2H)-one 生成 2',3a-dimethylspiro[5,6-dihydrofuro[2,3-d][1,3]dioxole-2,3'-oxolane]-2',6a-diol
  参考文献：
  名称：

  Laurencione, a heterocycle from the red alga Laurencia spectabilis

  摘要：

  Laurencione was isolated from Laurencia spectabilis and its structure determined to be an equilibrium mixture of (+/-)-2-hydroxy-2-methyldihydrofuran-3-one and 5-hydroxy-2,3-pentanedione. On silica gel, laurencione dimerized to optically inactive, crystalline spiro-bis-pinnaketal, a previously reported natural product of L. pinnatifida.

  DOI：

  10.1016/0031-9422(92)80276-k
• 作为产物：
  描述：

  5-acetoxy-3-chloro-3-ethylsulfanylpentan-2-one 在 mercury(II) diacetate 、 potassium carbonate 、 对甲苯磺酸 作用下， 反应 4.0h， 生成 (+/-)-2-Hydroxy-2-methyldihydrofuran-3(2H)-one
  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

• 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.
• Investigation of Reactive α-Dicarbonyl Compounds Generated from the Maillard Reactions of <scp>l</scp>-Methionine with Reducing Sugars via Their Stable Quinoxaline Derivatives
  作者：Yvonne V. Pfeifer、Lothar W. Kroh

  DOI：10.1021/jf1008988

  日期：2010.7.28

  The formation of a-dicarbonyl compounds was investigated in methionine-catalyzed (Mail lard reaction) thermal degradation of D-glucose, maltose, and dextrin 10 at three different pH values (3, 5, and 8). The a-dicarbonyl compounds were trapped as quinoxalines and could be quantified by HPLC and GC-MS. Formation of 1,4-dideoxypentodiulose from hexoses and disaccharides was evidenced for the first time. The use of L-methionine as the amino compound for the formation of 1,4-dideoxypentodiulose in model systems is explained. Furthermore, it could be shown that methionine has great effect on the formation of specific a-dicarbonyl compounds. At various pH values and also by application of mono-, di-, and oligosaccharides in all model reactions, 3-deoxyhexosulose and 1,4-dideoxypentodiulose were generated preferentially.
• One-Step Synthesis of Laurencione
  作者：Wim Aelterman、Norbert De Kimpe、Valery Kalinin

  DOI：10.1021/np960740e

  日期：1997.4.1

  The synthesis of the marine natural product laurencione from 5-hydroxy-2-pentanone in one step is reported.
• 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。
• Laurencione, a heterocycle from the red alga Laurencia spectabilis
  作者：Matthew W Bernart、William H Gerwick、Ethan E Corcoran、Angela Y Lee、Jon Clardy

  DOI：10.1016/0031-9422(92)80276-k

  日期：1992.4

  Laurencione was isolated from Laurencia spectabilis and its structure determined to be an equilibrium mixture of (+/-)-2-hydroxy-2-methyldihydrofuran-3-one and 5-hydroxy-2,3-pentanedione. On silica gel, laurencione dimerized to optically inactive, crystalline spiro-bis-pinnaketal, a previously reported natural product of L. pinnatifida.