(-)-(2S,3R)-2-methyl-5-oxotetrahydro-3-furancarboxylic acid | 681179-42-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (-)-(2S,3R)-2-methyl-5-oxotetrahydro-3-furancarboxylic acid
• 英文别名: (2S,3R)-2-methyl-5-oxooxolane-3-carboxylic acid
• CAS: 681179-42-0
• 化学式: C₆H₈O₄
• 分子量: 144.127
• InChiKey: VUQCNPSZDKJGCG-IUYQGCFVSA-N

物化性质

• 沸点：
  372.7±35.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-(2S,3R)-2-methyl-5-oxotetrahydro-3-furancarboxylic acid 在 N-甲基吗啉 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 、 水 为溶剂， 反应 3.08h， 生成 (4S,5S)-dihydro-4-acetoxymethyl-5-methyl-2(3H)-furanone
  参考文献：
  名称：

  A study of the enantiopreference of lipase PS (Pseudomonas cepacia) towards diastereomeric dihydro-5-alkyl-4-hydroxymethyl-2(3H)-furanones

  摘要：

  Lipase PS acetylation of diastereomeric dihydro-4-hydroxymethyl-2(3H)-furanones bearing a methyl or a pentyl group at C-5 have been studied. Higher enantioselectivities were found for the cis-isomers with respect to the trans-isomers. They were also higher for the systems bearing the longer alkyl chain. Lipase PS-catalyzed hydrolyses of racemic acetates were found to follow the same trend, although the efficiency of the enzyme was lower than in the acetylation reactions. These results were supported by molecular modelling studies that correctly predicted the maximum stereo selectivity for the cis-isomer of 5-pentyl substituted lactones both in acetylation and in hydrolysis reactions. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.036
• 作为产物：
  描述：

  乙酰琥珀酸二乙酯 在 盐酸 、 sodium tetrahydroborate 、 α-chymotrypsin 作用下， 以 1,4-二氧六环 、 phosphate buffer 、 乙醇 、 水 为溶剂， 反应 7.17h， 生成 (-)-(2S,3R)-2-methyl-5-oxotetrahydro-3-furancarboxylic acid
  参考文献：
  名称：

  化学酶促合成对映体富集的5-氧代-四氢-3-呋喃羧酸衍生物

  摘要：

  通过消旋的外消旋物，获得（ee）范围为60％至92％的（R）-（+）-对ac酸4，（S）-（-）-对苯二甲酸6及其相应的甲酯和乙酯。外消旋的γ-甲基对羟基苯甲酸乙酯14a和14b的酶解可分离未反应的酯（2 R，3 R）-（+）- 14a和内酯酸（2 S，3 R）-（-）- 5b的ee分别为80％和93％ee，前者使用马肝丙酮粉（HLAP），后者使用α-胰凝乳蛋白酶（α-CT）。对映体乙基（2通过面包酵母的乙酰丁二酸二乙酯的还原反应，获得了ee> 99％的S，3 S）-（-）- 14a和（2 S，3 R）-（-）- 14b。

  DOI：

  10.1016/j.tetasy.2004.01.001

文献信息

• Photochemical C-C Bond Formation between Alcohols and Olefins by an Environmentally Benign Radical Reaction
  作者：Akihiko Ouchi、Chuanxiang Liu、Masayuki Kaneda、Takeshi Hyugano

  DOI：10.1002/ejoc.201300115

  日期：2013.6

  A radical C–C bond formation between olefins and alcohols proceeded efficiently by simple light irradiation at room temperature. The reaction proceeded in the presence of commercially available tBuOOtBu without using the harmful elements and/or compounds that have an unpleasant smell that are often used in conventional radical reactions. In addition, the reaction did not require photosensitizers or

  在室温下，通过简单的光照射，烯烃和醇之间的自由基 C-C 键形成有效地进行。该反应在市售的 tBuOOtBu 存在下进行，不使用常规自由基反应中经常使用的有害元素和/或具有难闻气味的化合物。此外，该反应不需要光敏剂或光催化剂，这消除了反应后敏化剂的耗时分离，或之前程序中报道的光催化剂的合成。
• Chemoenzymatic synthesis of diastereomeric ethyl γ-benzyl paraconates and determination of the absolute configurations of their acids
  作者：Federico Berti、Fulvia Felluga、Cristina Forzato、Giada Furlan、Patrizia Nitti、Giuliana Pitacco、Ennio Valentin

  DOI：10.1016/j.tetasy.2006.08.013

  日期：2006.9

  resolution of the corresponding lactonic esters with α-chymotrypsin (α-CT) with acetone added as a cosolvent. Their absolute configurations were determined by 1H NMR analysis of their 1-(9-anthryl)-2,2,2-trifluoroethyl esters.

  对映体纯（99％ee）的顺式和反式-γ-苄基对圆锥体酸及其乙酯是通过以下方法合成的：将相应的内酯与α-胰凝乳蛋白酶（α-CT）进行动力学酶解，并加入丙酮作为助溶剂。通过其1-（9-蒽基）-2,2,2-三氟乙基酯的1 H NMR分析确定其绝对构型。
• Chemoenzymatic synthesis of enantioenriched 5-oxo-tetrahydro-3-furancarboxylic acid derivatives
  作者：Andrea Comini、Cristina Forzato、Patrizia Nitti、Giuliana Pitacco、Ennio Valentin

  DOI：10.1016/j.tetasy.2004.01.001

  日期：2004.2

  (R)-(+)-Paraconic acid 4, (S)-(−)-terebic acid 6 and their corresponding methyl and ethyl esters having ee’s ranging from 60% to 92% were obtained by enzymatic resolution of their racemates. The enzymatic resolution of racemic ethyl γ-methylparaconates 14a and 14b allowed the isolation of the unreacted ester (2R,3R)-(+)-14a and that of the lactonic acid (2S,3R)-(−)-5b with 80% and 93% ee, respectively

  通过消旋的外消旋物，获得（ee）范围为60％至92％的（R）-（+）-对ac酸4，（S）-（-）-对苯二甲酸6及其相应的甲酯和乙酯。外消旋的γ-甲基对羟基苯甲酸乙酯14a和14b的酶解可分离未反应的酯（2 R，3 R）-（+）- 14a和内酯酸（2 S，3 R）-（-）- 5b的ee分别为80％和93％ee，前者使用马肝丙酮粉（HLAP），后者使用α-胰凝乳蛋白酶（α-CT）。对映体乙基（2通过面包酵母的乙酰丁二酸二乙酯的还原反应，获得了ee> 99％的S，3 S）-（-）- 14a和（2 S，3 R）-（-）- 14b。
• A study of the enantiopreference of lipase PS (Pseudomonas cepacia) towards diastereomeric dihydro-5-alkyl-4-hydroxymethyl-2(3H)-furanones
  作者：Federico Berti、Cristina Forzato、Patrizia Nitti、Giuliana Pitacco、Ennio Valentin

  DOI：10.1016/j.tetasy.2005.01.036

  日期：2005.3

  Lipase PS acetylation of diastereomeric dihydro-4-hydroxymethyl-2(3H)-furanones bearing a methyl or a pentyl group at C-5 have been studied. Higher enantioselectivities were found for the cis-isomers with respect to the trans-isomers. They were also higher for the systems bearing the longer alkyl chain. Lipase PS-catalyzed hydrolyses of racemic acetates were found to follow the same trend, although the efficiency of the enzyme was lower than in the acetylation reactions. These results were supported by molecular modelling studies that correctly predicted the maximum stereo selectivity for the cis-isomer of 5-pentyl substituted lactones both in acetylation and in hydrolysis reactions. (C) 2005 Elsevier Ltd. All rights reserved.