cis-2H,5H-dihydrofuran-2,5-dicarboxylic acid | 2043-98-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: cis-2H,5H-dihydrofuran-2,5-dicarboxylic acid
• 英文别名: cis-2,5-Dihydrofuran-2,5-dicarboxylic Acid；2,5-dihydro-furan-2r,5c-dicarboxylic acid；2,5-Dihydro-furan-2r,5c-dicarbonsaeure；2,5-Dihydro-furan-2,5-dicarbonsaeure；2,5-Dihydro-furan-cis-2,5-dicarbonsaeure；2,5-Anhydro-3,4-dideoxy-D-erythro-hex-3-enaric acid；(2S,5R)-2,5-dihydrofuran-2,5-dicarboxylic acid
• CAS: 2043-98-3
• 化学式: C₆H₆O₅
• 分子量: 158.111
• InChiKey: VRDWCLRWRUCGPB-ZXZARUISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  cis-2H,5H-dihydrofuran-2,5-dicarboxylic acid 生成 cis-2,5-Bis(hydroxymethyl)-2,5-dihydrofuran
  参考文献：
  名称：

  Synthesis of a triazole homo-C-nucleoside

  摘要：

  DOI：

  10.1021/jo00330a004
• 作为产物：
  描述：

  2,5-呋喃二甲酸 在 氨 、 sodium 、 异丙醇 作用下， 反应 0.5h， 以43%的产率得到cis-2H,5H-dihydrofuran-2,5-dicarboxylic acid
  参考文献：
  名称：

  Enzymes in organic synthesis. 48. Pig liver esterase and porcine pancreatic lipase catalyzed hydrolyses of 3,4-(isopropylidenedioxy)-2,5-tetrahydrofuranyl diesters

  摘要：

  Pig liver esterase (PLE) and porcine pancreatic lipase (PPL) catalyzed hydrolyses of 2,5-bis(methoxycarbonyl) and 2,5-bis(acetoxymethyl) meso-diester derivatives of 3,4-(isopropylidenedioxy) tetrahydrofuran proceed with enantiotopic selectivity to give monoester products of up to 72% ee. Transesterification of the 2,5-bis(hydroxymethyl) derivative with trifluorethyl laurate promoted by PPL in ether also proceeds stereoselectively but in the opposite stereochemical sense from the hydrolysis of the corresponding diacetate. The data provide further examples of heteroatom and ester moiety induced reversals of stereoselectivity for the two enzymes.

  DOI：

  10.1021/jo00018a033

文献信息

• Seelig, Chemische Berichte, 1879, vol. 12, p. 1085
  作者：Seelig

  DOI：——

  日期：——
• Hill; Wheeler, American Chemical Journal, 1901, vol. 25, p. 463,466, 474, 480
  作者：Hill、Wheeler

  DOI：——

  日期：——
• Schroetter, Monatshefte fur Chemie, 1888, vol. 9, p. 443
  作者：Schroetter

  DOI：——

  日期：——
• Enzymes in organic synthesis. 48. Pig liver esterase and porcine pancreatic lipase catalyzed hydrolyses of 3,4-(isopropylidenedioxy)-2,5-tetrahydrofuranyl diesters
  作者：Philip G. Hultin、Franz Josef Mueseler、J. Bryan Jones

  DOI：10.1021/jo00018a033

  日期：1991.8

  Pig liver esterase (PLE) and porcine pancreatic lipase (PPL) catalyzed hydrolyses of 2,5-bis(methoxycarbonyl) and 2,5-bis(acetoxymethyl) meso-diester derivatives of 3,4-(isopropylidenedioxy) tetrahydrofuran proceed with enantiotopic selectivity to give monoester products of up to 72% ee. Transesterification of the 2,5-bis(hydroxymethyl) derivative with trifluorethyl laurate promoted by PPL in ether also proceeds stereoselectively but in the opposite stereochemical sense from the hydrolysis of the corresponding diacetate. The data provide further examples of heteroatom and ester moiety induced reversals of stereoselectivity for the two enzymes.
• Synthesis of a triazole homo-C-nucleoside
  作者：Walter J. Gensler、Sum Chan、David B. Ball

  DOI：10.1021/jo00330a004

  日期：1981.8