| 144027-37-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• CAS: 144027-37-2
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: XVWUCMOKLRQMJD-UHFFFAOYSA-N

物化性质

• 沸点：
  200.8±10.0 °C(Predicted)
• 密度：
  0.829±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  在 palladium dichloride magnesium sulfate 、 原乙酸三乙酯 、 pyridinium chlorochromate 、 methyloxirane 、 copper dichloride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 (+/-)-methyl 2-(5'-ethyl-5'-methoxytetrahydrofuran-2'-yl)-propenoate
  参考文献：
  名称：

  Furanosides and furanones bearing acrylate sidechains via palladium-mediated cyclizations of γ-Oxoallenes

  摘要：

  Treatment of 4,5-hexadienal with catalytic palladium(II) chloride and excess copper(II) chloride, methanol and carbon monoxide in the presence of an acid and a water scavenger resulted in a net acetalization-cyclization-methoxycarbonylation to form a novel methyl furanoside bearing a methyl acrylate sidechain. Treatment of 4,5-hexadienoic acid under the same conditions yields the corresponding furanone, and 3-(tert-butylidimethylsilyloxy)-4,5-hexadienal yields a methyl beta-3'-(tert-butyldimethylsilyloxy)-2'-deoxyribofuranoside bearing the acrylate sidechain, with high stereoselectivity. This methodology provides access to sidechain-branched ribofuranoside compounds.

  DOI：

  10.1016/0040-4020(93)80015-l
• 作为产物：
  描述：

  hexa-4,5-dienal 、 乙基溴化镁 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Furanosides and furanones bearing acrylate sidechains via palladium-mediated cyclizations of γ-Oxoallenes

  摘要：

  Treatment of 4,5-hexadienal with catalytic palladium(II) chloride and excess copper(II) chloride, methanol and carbon monoxide in the presence of an acid and a water scavenger resulted in a net acetalization-cyclization-methoxycarbonylation to form a novel methyl furanoside bearing a methyl acrylate sidechain. Treatment of 4,5-hexadienoic acid under the same conditions yields the corresponding furanone, and 3-(tert-butylidimethylsilyloxy)-4,5-hexadienal yields a methyl beta-3'-(tert-butyldimethylsilyloxy)-2'-deoxyribofuranoside bearing the acrylate sidechain, with high stereoselectivity. This methodology provides access to sidechain-branched ribofuranoside compounds.

  DOI：

  10.1016/0040-4020(93)80015-l

文献信息

• A palladium-catalyzed cyclization-carbonylation-coupling reaction between aryl halides and γ-Hydroxyallenes to form aryl (tetrahydrofuran-2-yl)vinyl ketones
  作者：Robert D. Walkup、Lufeng Guan、Young Soo Kim、Sang Woong Kim

  DOI：10.1016/0040-4039(95)00666-z

  日期：1995.5

  γ-Hydroxyallenes undergo cyclization-carbonylation-coupling with aryl (and one alkenyl) halides in the presence of catalytic Pd(PPh3)4, base, and CO to form the title ketones in good yields. The reaction was temperature dependent: at 80 °C, the CO insertion did not readily occur, while at 55–60 °C the ketone products predominated. Yields for the Pd(0)-catalyzed cyclization-coupling reaction (without

  在催化性Pd（PPh 3）4，碱和CO的存在下，γ-羟基丙烯与芳基（和一个烯基）卤化物进行环化-羰基化偶联，以高收率形成标题酮。反应取决于温度：在80°C下，CO的插入不容易发生，而在55–60°C下，酮类产品占主导地位。添加-丁基异氰化物（不存在CO）时，Pd（0）催化的环化偶联反应（无插入）的收率提高，这表明良好的π酸配体可改善芳基钯（II）卤化物之间的环化偶联反应和γ-羟基丙二烯。
• Access to -2,5-disubstituted iodovinyltetrahydrofurans via the cyclization of γ-silyloxyallenes using n-iodosuccinimide
  作者：Robert D Walkup、Lufeng Guan、Sang Woong Kim、Young Soo Kim

  DOI：10.1016/0040-4039(92)88075-g

  日期：1992.7

  Treatment of gamma-(tert-butyldimethylsiloxy)- or gamma-(trimethylsiloxy)allenes bearing various groups at the ether carbon with N-iodosuccinimide resulted in the formation of iodocyclization products, 1-iodo-1-(tetrahydrofuran-2'-yl)ethenes, in good yields and with high selectivity for the cis diastereomer.
• Furanosides and furanones bearing acrylate sidechains via palladium-mediated cyclizations of γ-Oxoallenes
  作者：Robert D. Walkup、Michael D. Mosher

  DOI：10.1016/0040-4020(93)80015-l

  日期：1993.1

  Treatment of 4,5-hexadienal with catalytic palladium(II) chloride and excess copper(II) chloride, methanol and carbon monoxide in the presence of an acid and a water scavenger resulted in a net acetalization-cyclization-methoxycarbonylation to form a novel methyl furanoside bearing a methyl acrylate sidechain. Treatment of 4,5-hexadienoic acid under the same conditions yields the corresponding furanone, and 3-(tert-butylidimethylsilyloxy)-4,5-hexadienal yields a methyl beta-3'-(tert-butyldimethylsilyloxy)-2'-deoxyribofuranoside bearing the acrylate sidechain, with high stereoselectivity. This methodology provides access to sidechain-branched ribofuranoside compounds.