Methyl R-(+)-tetrahydro-2-methyl-5-oxo-2-furanacetate | 129250-83-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Methyl R-(+)-tetrahydro-2-methyl-5-oxo-2-furanacetate
• 英文别名: methyl 2-[(2R)-2-methyl-5-oxooxolan-2-yl]acetate
• CAS: 129250-83-5
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: YBONZTCKXPZVAN-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2R,3R)-3-methyl-3-(4-methyl-3-pentenyl)oxiranemethanol 在 chromium(VI) oxide 、 硫酸 、 水 、 臭氧 、 红铝 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 4.5h， 生成 Methyl R-(+)-tetrahydro-2-methyl-5-oxo-2-furanacetate
  参考文献：
  名称：

  真菌颜料，第16部分。（R）-（+）-四氢-2-甲基-5-氧代-2-呋喃乙酸甲酯及其（S）-（-）-正电极的合成，用于绝对值测定的手性参考真菌前蒽醌的立体化学。

  摘要：

  通过香叶醇的不对称环氧化反应合成（R）-和（S）-丁醇化物7和9。（R）-丁醇化物7也由（S）-柠檬酸获得。丁醇化物7和9是用于测定真菌和植物前蒽醌中绝对立体化学的有价值的参考化合物。

  DOI：

  10.1016/s0957-4166(00)86350-8

文献信息

• Pigments of fungi, part 19. A degradative method for the determination of central chirality in naturally occurring 3-hydroxy-3-methyl-3,4-dihydroanthracen-1(2H)-ones: Application to pigments of the flavomannin type.
  作者：Melvyn Gill、Alberto Giménez、Akhil G. Jhingran、Anna R. Palfreyman

  DOI：10.1016/0957-4166(90)80012-n

  日期：1990.1
• A degradative method for the determination of central chirality in naturally occurring 3-hydroxy-3-methyl-3,4-dihydroanthracen-1(2H)ones.
  作者：Melvyn Gill、Alberto Gimenez、Akhil G. Jhingran、Anna R. Palfreyman

  DOI：10.1016/s0040-4039(00)88766-3

  日期：1990.1
• Gill, Melvyn; Smrdel, Albin F.; Strauch, Richard J., Journal of the Chemical Society. Perkin transactions I, 1990, # 6, p. 1583 - 1592
  作者：Gill, Melvyn、Smrdel, Albin F.、Strauch, Richard J.、Begley, Michael J.

  DOI：——

  日期：——
• The absolute configuration of peroxisomicines A1 and A2
  作者：Alejandro Pérez、Rosalba Ramírez-Durón、Alfredo Piñeyro-López、Noemí Waksman、Matthias Reichert、Gerhard Bringmann

  DOI：10.1016/j.tet.2004.06.123

  日期：2004.9

  Peroxisomicine A1 is a potentially antineoplastic compound isolated from the seeds of Karwinskia parvifolia. It is considered as a useful chemotype for the preparation of topoisomerase II targeted anticancer cells. Stereochemically, it is characterized by the presence of two stereocenters and a rotationally hindered and thus likewise stereogenic biaryl axis. In this contribution, the absolute configuration of peroxisomicine A1 and its epimer, peroxisomicine A2, was established by means of a five-step degradative procedure giving the respective R- and S-configured methyl 2-(2'-methyl-5'-oxotetrahydrofuryl)acetates. The configuration of the degradation product was obtained by means of optical rotation, H-1 NMR analysis using a chiral displacement reagent, and by experimental and quantum chemical circular dichroism (CD) investigations. Based on the results obtained here and considering our previous work on the relative configuration at centers versus axis of these compounds, peroxisomicine A1 resulted to be the P,3S,3'S-isomer and peroxisomicine A2 the P,3R,3'S-isomer. (C) 2004 Elsevier Ltd. All rights reserved.
• GILL, METVYN;GIMENEZ, ALBERTO;JHINGRAN, AKHIL G.;PALFREYMAN, ANNA R., TETRAHEDRON. LETT., 31,(1990) N, C. 1203-1206
  作者：GILL, METVYN、GIMENEZ, ALBERTO、JHINGRAN, AKHIL G.、PALFREYMAN, ANNA R.

  DOI：——

  日期：——