5-Benzenesulfonylmethyl-2-methoxy-furan-3-carboxylic acid methyl ester | 128496-95-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 5-Benzenesulfonylmethyl-2-methoxy-furan-3-carboxylic acid methyl ester
• 英文别名: Methyl 5-(benzenesulfonylmethyl)-2-methoxyfuran-3-carboxylate
• CAS: 128496-95-7
• 化学式: C₁₄H₁₄O₆S
• 分子量: 310.328
• InChiKey: LPXPJHCTGNVNOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  91.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3-Dibromo-1-(phenylsulfonyl)-1-propene 在 potassium tert-butylate 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 15.5h， 生成 5-Benzenesulfonylmethyl-2-methoxy-furan-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Tunable regioselectivity associated with the reaction of 2,3-dihalo-1-(phenylsulfonyl)-1-propenes with ambident nucleophilic reagents

  摘要：

  2,3-Dihalo-1-(phenylsulfonyl)-1-propenes, obtained by the addition of bromine or iodine onto (phenylsulfonyl)propadiene, were found to exhibit interesting reactivity as both mono- and dielectrophiles, with the mode of reactivity depending upon the nature of the nucleophile as well as the reaction conditions. Thus, amines or thiophenols smoothly effected substitution at the allylic site, while sodium methoxide reacted at the vinylic position through an addition-elimination process. In the realm of ambident nucleophiles, beta-dicarbonyl compounds in a medium of NaH/tert-butoxide/THF gave 2-alkyl-3-acyl-4-[(phenylsulfonyl)methyl]furans, produced by initial allylic S(N)2 displacement followed by 5-exo-trig cyclization. Conversely, such beta-dicarbonyls in a methoxide/methanol system yielded 2-alkyl-4-[(phenylsulfonyl)methyl]furans, where reaction proceeds by initial addition-elimination on the vinyl sulfone moiety. In contrast, silyl enol ethers in the presence of silver tetrafluoroborate resulted in products derived from S(N)2 displacement at the allylic site. Thioamides could be used to form 2-substituted thiazoles by initial allylic displacement by the sulfur atom followed by an addition-elimination reaction. Thus, a variety of compounds were prepared from 2,3-dihalo-1-(phenylsulfonyl)-1-propenes by the proper choice of reagents and reaction conditions.

  DOI：

  10.1021/jo00030a024

文献信息

• Rapid and facile synthesis of highly substituted furans
  作者：David I MaGee、James D Leach

  DOI：10.1016/s0040-4039(97)10183-6

  日期：1997.11

  A short and efficient synthesis of highly substituted furans has been accomplished. The method is amenable for the production of 2,5-di, 2,3,5-tri and 2,3,4,5-tetrasubstituted furan compounds containing multiple functionalities.

  已经完成了短而有效的高度取代的呋喃的合成。该方法适合于生产含有多种官能度的2，5-二，2，3，5-三和2，3，4，5-四取代的呋喃化合物。
• Use of 2,3-dibromo-1-(phenylsulfonyl)-1-propene as a reagent for the synthesis of annulated furans
  作者：Albert Padwa、S. Shaun Murphree、Philip E. Yeske

  DOI：10.1021/jo00301a006

  日期：1990.7
• PADWA, ALBERT;MURPHREE, S. SHAUN;YESKE, PHILIP E., J. ORG. CHEM., 55,(1990) N4, C. 4241-4242
  作者：PADWA, ALBERT、MURPHREE, S. SHAUN、YESKE, PHILIP E.

  DOI：——

  日期：——
• Tunable regioselectivity associated with the reaction of 2,3-dihalo-1-(phenylsulfonyl)-1-propenes with ambident nucleophilic reagents
  作者：Albert Padwa、David J. Austin、Masaru Ishida、Cheryl L. Muller、S. Shaun Murphree、Philip E. Yeske

  DOI：10.1021/jo00030a024

  日期：1992.2

  2,3-Dihalo-1-(phenylsulfonyl)-1-propenes, obtained by the addition of bromine or iodine onto (phenylsulfonyl)propadiene, were found to exhibit interesting reactivity as both mono- and dielectrophiles, with the mode of reactivity depending upon the nature of the nucleophile as well as the reaction conditions. Thus, amines or thiophenols smoothly effected substitution at the allylic site, while sodium methoxide reacted at the vinylic position through an addition-elimination process. In the realm of ambident nucleophiles, beta-dicarbonyl compounds in a medium of NaH/tert-butoxide/THF gave 2-alkyl-3-acyl-4-[(phenylsulfonyl)methyl]furans, produced by initial allylic S(N)2 displacement followed by 5-exo-trig cyclization. Conversely, such beta-dicarbonyls in a methoxide/methanol system yielded 2-alkyl-4-[(phenylsulfonyl)methyl]furans, where reaction proceeds by initial addition-elimination on the vinyl sulfone moiety. In contrast, silyl enol ethers in the presence of silver tetrafluoroborate resulted in products derived from S(N)2 displacement at the allylic site. Thioamides could be used to form 2-substituted thiazoles by initial allylic displacement by the sulfur atom followed by an addition-elimination reaction. Thus, a variety of compounds were prepared from 2,3-dihalo-1-(phenylsulfonyl)-1-propenes by the proper choice of reagents and reaction conditions.