(+/-)-(3RS,4RS,5SR)-3-hydroxy-4,5-(isopropylidenedioxy)cyclohexanone | 74293-60-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-(3RS,4RS,5SR)-3-hydroxy-4,5-(isopropylidenedioxy)cyclohexanone
• 英文别名: (3aR,7S,7aS)-7-hydroxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-1,3-benzodioxol-5-one
• CAS: 74293-60-0；134003-06-8
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: HIBBXJIPTYECSL-RNJXMRFFSA-N

物化性质

• 沸点：
  323.0±42.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  7-oxabicyclo<2.2.1>hepta-2,3-diol-5-one, isopropyl acetal 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以85%的产率得到(+/-)-(3RS,4RS,5SR)-3-hydroxy-4,5-(isopropylidenedioxy)cyclohexanone
  参考文献：
  名称：

  通过光化学诱导的电子转移进行自由基阴离子开环反应

  摘要：

  烷基自由基阴离子可以诱导相邻的应变环如环丙烷，环丁烷，环氧化物和7-氧杂双环[2.2.1]庚烷的打开。

  DOI：

  10.1016/s0040-4039(00)79654-7

文献信息

• Reductive Oxa Ring Opening of 7-Oxabicyclo[2.2.1]heptan-2-ones. Synthesis of C-.alpha.-Galactosides of Carbapentopyranoses
  作者：Janine Cossy、Jean-Luc Ranaivosata、Veronique Bellosta、Jacek Ancerewicz、Rafael Ferritto、Pierre Vogel

  DOI：10.1021/jo00131a007

  日期：1995.12

  Photoinduced electron transfer from Et(3)N to 7-oxabicyclo[2.2.1]heptan-2-ones can generate the corresponding 3-hydroxycyclohexanone derivatives. The method has been applied to the synthesis of C-alpha-D-galactopyranosides of carbapentopyranoses. Radical alpha-D-galactosidation of (+/-)-(1RS,4RS,5RS, 6RS)-6-endo-methoxy-3-methylidene-5-exo-(phenylseleno)-7-oxabicyclo[2.2.l]hept-2-one ((+)-51) followed by seleno-Pummerer rearrangement and reduction with Bu(3)SnH gave (+)- (1R,2S,3S,4R,6R)-((+)-58) and (+)-(1S,2R,3R,4S,6S)-3-endo-methoxy-5-oxo-6-endo-[(2',3',4',6'-tetra-0-acetyl-alpha-D-galactopyranosyl)methyl]-7-oxabicyclo[2.2.1]hept-2-endo-yl acetate ((+)-59), which were separated by column chromatography. Irradiation (254 nn) in the presence of Et(3)N gave (+)-(1S,2R,3R,6R)-((+)-60) and (+)-(1R,2S,3S,6S)-2-hydroxy-6-methoxy-4-oxo-3-[(2',3',4',6'-tetra-0-acetyl-alpha-D-galactopyranosyl)methyl]cyclohexyl acetate (+)-61, respectively. NaBH4 reduction and acetylation provided (+)-(1S,2S,3R,4R,5R)-((+)-62) and (+)-(1R,2R,3S,4S,5S)-5-methoxy-2-[(2',3',4',6'-tetra-0-acetyl-alpha-D-galactopyranosyl)methyl]cyclohexa-1,3,4-triyl triacetate ((+)-64).