(R)-tetrahydro-5-oxofuran-2-acetic acid | 63597-98-8

• 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: (R)-tetrahydro-5-oxofuran-2-acetic acid
• 英文别名: hydroxyadipic acid-γ-lactone；(R)-2-(5-Oxotetrahydrofuran-2-yl)acetic acid；2-[(2R)-5-oxooxolan-2-yl]acetic acid
• CAS: 63597-98-8
• 化学式: C₆H₈O₄
• 分子量: 144.127
• InChiKey: BWEICTHJUIJQPH-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  2
• 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：

  (R)-tetrahydro-5-oxofuran-2-acetic acid 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到(R)-5-(2-hydroxyethyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  （R）-四氢-5-氧代-2-（2-羟乙基）呋喃的化学酶促方法，一种有用的手性合成子：在合成（S）-4-己内酯，信息素对映体中的应用。

  摘要：

  多功能手性合成子6的合成已通过面包酵母的介导还原反应完成，该还原反应还用于合成8种储存的谷物害虫的信息素对映体。

  DOI：

  10.1016/s0040-4020(01)96037-5
• 作为产物：
  描述：

  (R)-3-羟基己二酸 在 盐酸 、 水 作用下， 反应 0.17h， 生成 (R)-tetrahydro-5-oxofuran-2-acetic acid
  参考文献：
  名称：

  Mycenaaurin A, an Antibacterial Polyene Pigment from the Fruiting Bodies of Mycena aurantiomarginata

  摘要：

  A new polyene pigment, mycenaaurin A (1), was isolated from fruiting bodies of Mycena aurantiomarginata. Mycenaaurin A consists of a tridecaketide that is flanked by two amino acid moieties. These are likely to be derived biosynthetically from S-adenosylmethionine. The tridecaketide itself contains an alpha-pyrone, a conjugated hexaene, and an isolated alkenyl moiety. The structure of the new pigment was established by 2D NMR spectroscopic methods and APCIMS. The absolute configuration of the four stereogenic centers was determined by degradation of 1 by ozonolysis and GC-MS comparison of the resulting fragments, after appropriate derivatization, with authentic synthetic samples. Mycenaaurin A (1) might act as a constitutive defense compound, since it exhibits antibacterial activity against the Gram-positive bacterium Bacillus pumilus.

  DOI：

  10.1021/np100155z

文献信息

• The enzymatic baeyer-villiger oxidation: A study of 4-substituted cyclohexanones
  作者：Michael J. Taschner、Donald J. Black、Quin-Zene Chen

  DOI：10.1016/s0957-4166(00)80248-7

  日期：1993.6

  A study of the enzymatic Baeyer-Villiger oxidation of a number of 4-substituted cyclohexanones utilizing the enzyme cyclohexanone oxygenase (E.C. 1.14.13.-), isolated from the bacteria Acinetobacter NCIB 9871, is described.
• CAPRARO, HANS-GEORG;FRANCOTTE, ERIC;KOHLER, BORIS;RIHS, GRETHY;SCHNEIDER,+, J. ANTIBIOTICS, 41,(1988) N 6, 759-770
  作者：CAPRARO, HANS-GEORG、FRANCOTTE, ERIC、KOHLER, BORIS、RIHS, GRETHY、SCHNEIDER,+

  DOI：——

  日期：——
• KATO Y.; WAKABAYASHI T., SYNTH. COMMUNS, 1977, 7, NO 2, 125-130 D=#2#
  作者：KATO Y.、 WAKABAYASHI T.

  DOI：——

  日期：——
• Mycenaaurin A, an Antibacterial Polyene Pigment from the Fruiting Bodies of <i>Mycena aurantiomarginata</i>
  作者：Robert J. R. Jaeger、Peter Spiteller

  DOI：10.1021/np100155z

  日期：2010.8.27

  A new polyene pigment, mycenaaurin A (1), was isolated from fruiting bodies of Mycena aurantiomarginata. Mycenaaurin A consists of a tridecaketide that is flanked by two amino acid moieties. These are likely to be derived biosynthetically from S-adenosylmethionine. The tridecaketide itself contains an alpha-pyrone, a conjugated hexaene, and an isolated alkenyl moiety. The structure of the new pigment was established by 2D NMR spectroscopic methods and APCIMS. The absolute configuration of the four stereogenic centers was determined by degradation of 1 by ozonolysis and GC-MS comparison of the resulting fragments, after appropriate derivatization, with authentic synthetic samples. Mycenaaurin A (1) might act as a constitutive defense compound, since it exhibits antibacterial activity against the Gram-positive bacterium Bacillus pumilus.
• A chemoenzymatic approach to (R)-tetrahydro-5-oxo-2-(2-hydroxyethyl)furan, a useful chiral synthon: Application to the synthesis of (S)-4-hexanolide, pheromone antipode of .
  作者：S.K. Ghosh、S. Chattopadhyay、V.R. Mamdapur

  DOI：10.1016/s0040-4020(01)96037-5

  日期：1991.5

  A synthesis of versatile chiral synthon 6 has been accomplished via a baker's yeast mediated reduction, which was further utilized for the synthesis of 8, pheromone antipode of stored grain pest.

  多功能手性合成子6的合成已通过面包酵母的介导还原反应完成，该还原反应还用于合成8种储存的谷物害虫的信息素对映体。