5-Hydroxymethyl-3-phenyl-furan-2-carboxylic acid tert-butyl ester | 379669-86-0

• 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-Hydroxymethyl-3-phenyl-furan-2-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 5-(hydroxymethyl)-3-phenylfuran-2-carboxylate
• CAS: 379669-86-0
• 化学式: C₁₆H₁₈O₄
• 分子量: 274.317
• InChiKey: OMTORIIUFJKJIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Hydroxymethyl-3-phenyl-furan-2-carboxylic acid tert-butyl ester 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 以98%的产率得到5-Methyl-3-phenyl-furan-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  A novel approach to the synthesis of 4-aryl-furan-3-ols

  摘要：

  A novel, yet simple, method for the synthesis of 4-aryl-furan-3-ols is described. The condensation between dimethyl diglycolate I and various aryl glyoxylates 2 using KOt-Bu as base furnished a series of 4-aryl-furan-3-ols 4 bearing one tert-butyl ester and one methyl ester substituent. Such a mixed ester allowed easy differentiation of the two esters for selective chemical modification. In addition, these 4-aryl-furan-3-ols could be further transformed to other useful substituted furans. through conversion to the triflates and subsequent metal-mediated reduction or coupling. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01284-9
• 作为产物：
  描述：

  苯甲酰甲酸甲酯 在 bis-triphenylphosphine-palladium(II) chloride 甲酸 、 sodium methylate 、 三乙基硼氢化锂 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 生成 5-Hydroxymethyl-3-phenyl-furan-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  A novel approach to the synthesis of 4-aryl-furan-3-ols

  摘要：

  A novel, yet simple, method for the synthesis of 4-aryl-furan-3-ols is described. The condensation between dimethyl diglycolate I and various aryl glyoxylates 2 using KOt-Bu as base furnished a series of 4-aryl-furan-3-ols 4 bearing one tert-butyl ester and one methyl ester substituent. Such a mixed ester allowed easy differentiation of the two esters for selective chemical modification. In addition, these 4-aryl-furan-3-ols could be further transformed to other useful substituted furans. through conversion to the triflates and subsequent metal-mediated reduction or coupling. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01284-9

文献信息

• A novel approach to the synthesis of 4-aryl-furan-3-ols
  作者：Bruno Tse、A.Brian Jones

  DOI：10.1016/s0040-4039(01)01284-9

  日期：2001.9

  A novel, yet simple, method for the synthesis of 4-aryl-furan-3-ols is described. The condensation between dimethyl diglycolate I and various aryl glyoxylates 2 using KOt-Bu as base furnished a series of 4-aryl-furan-3-ols 4 bearing one tert-butyl ester and one methyl ester substituent. Such a mixed ester allowed easy differentiation of the two esters for selective chemical modification. In addition, these 4-aryl-furan-3-ols could be further transformed to other useful substituted furans. through conversion to the triflates and subsequent metal-mediated reduction or coupling. (C) 2001 Elsevier Science Ltd. All rights reserved.