trans-octahydro-2H-cycloheptafuran-2-one | 3724-99-0

• 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: trans-octahydro-2H-cycloheptafuran-2-one
• 英文别名: trans-octahydro-2H-cyclohepta[b]furan-2-one；(3aR,8aS)-3,3a,4,5,6,7,8,8a-octahydrocyclohepta[b]furan-2-one
• CAS: 3724-99-0；4401-23-4；52294-85-6
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: BLYGHAHUKQLNAC-SFYZADRCSA-N

物化性质

• 沸点：
  146-150 °C(Press: 10 Torr)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-octahydro-2H-cycloheptafuran-2-one 在 chromium(VI) oxide 、 硫酸 作用下， 以 四氢呋喃 、 乙醚 、 丙酮 为溶剂， 生成 trans-2-Acetoxycycloheptancarbonsaeure
  参考文献：
  名称：

  Uusvuori,R. et al., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1978, vol. 32, p. 531 - 535

  摘要：

  DOI：
• 作为产物：
  描述：

  (3aR,8aR)-3,3-Dichloro-octahydro-cyclohepta[b]furan-2-one 在 四甲基乙二胺 、 溶剂黄146 、 锌 作用下， 以 乙酸乙酯 为溶剂， 生成 trans-octahydro-2H-cycloheptafuran-2-one
  参考文献：
  名称：

  Sterically guided rearrangement of 3,3-disubstited β-lactones. A rapid construction of cycloheptano trans-fused butyrolactones

  摘要：

  DOI：

  10.1016/s0040-4039(00)97129-6

文献信息

• Diastereocontrol for Highly Enantioselective Carbon-Hydrogen Insertion Reactions of Cycloalkyl Diazoacetates
  作者：Michael P. Doyle、Alexey B. Dyatkin、Gregory H. P. Roos、Fina Canas、Deborah A. Pierson、Arjan van Basten、Paul Mueller、Philippe Polleux

  DOI：10.1021/ja00089a062

  日期：1994.5

  Intramolecular carbon-hydrogen insertion of metal carbenes generated by catalytic diazo decomposition of diazocarbonyl compounds is a facile methodology for carbon-carbon bond formation.1-3 Although there are notable exceptions,& five- membered-ring formation is preferred,7J and regioselectivity is generally subject to defined electronic effects.9JO Enantiocontrol has recently been achieved with selected

  通过重氮羰基化合物的催化重氮分解产生的金属卡宾的分子内碳氢插入是形成碳碳键的简便方法。 1-3 尽管有明显的例外，但优选五元环形成，7J 和区域选择性是通常受确定的电子效应影响。9JO 最近通过使用手性或同手性二铑 (I1) 羧酰胺、11J2 或羧酸盐、~~J~ 但即使使用四[甲基] 二铑 (I1)
• Ruthenium-Catalyzed Cycloisomerization−Oxidation of Homopropargyl Alcohols. A New Access to γ-Butyrolactones
  作者：Barry M. Trost、Young H. Rhee

  DOI：10.1021/ja992013m

  日期：1999.12.1

  Vinylidenemetal species, which readily form from terminal alkynes under mild conditions, have rarely been utilized as reactive intermediates in a catalytic cycle. The conversion of homopropargyl alcohols via such intermediates to metal-complexed oxacarbenes led to the development of an "oxidant" compatible with a ruthenium complex capable of performing the cycloisomerization, that would convert them to lactones. None of the oxidants known to stoichiometrically convert isolated metallooxacarbenes to esters are effective. The unconventional "oxidants", N-hydroxyimides, proved to be capable of effecting the desired transformation, with N-hydroxysuccinimide being the "oxidant" of choice. The procedure of choice employs cyclopentadienyl (1,4-cyclooctadiene) ruthenium chloride and trifuryl phosphine as the precatalyst in the presence of tetra-n-butylammonium bromide or hexafluorophosphate with N-hydroxysuccinimide as the oxidant in DMF-water at 95 degrees. In this way, a wide diversity of homopropargyl alcohols were converted to gamma-butyrolactones with excellent chemoselectivity. Lactones synthesized include an intermediate toward a platelet aggregation inhibitor, a fruit flavor principle, an inhibitor of binding of phorbol esters to PKC-alpha, a tobacco constituent, a wood constituent (quercus lactone), an aldosterone antagonist (spironolactone) precursor, and an acetogenin known for pesticidal and antitumor activities (muricatacin).
• Manganese(III)-mediated .gamma.-lactone annulation
  作者：William E. Fristad、John R. Peterson

  DOI：10.1021/jo00201a003

  日期：1985.1
• Doyle Michael P., Dyatkin Alexey B., Roos Gregory H. P., Canas Fina, Pier+, J. Amer. Chem. Soc., 116 (1994) N 10, S 4507-4508
  作者：Doyle Michael P., Dyatkin Alexey B., Roos Gregory H. P., Canas Fina, Pier+

  DOI：——

  日期：——