(+/-)-3-(t-butyldimethylsilyloxy)-4,5-hexadien-1-ol | 154366-15-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (+/-)-3-(t-butyldimethylsilyloxy)-4,5-hexadien-1-ol
• CAS: 154366-15-1
• 化学式: C₁₂H₂₄O₂Si
• 分子量: 228.407
• InChiKey: FBPCUPAQSYWCFT-UHFFFAOYSA-N

物化性质

• 沸点：
  278.4±25.0 °C(predicted)
• 密度：
  0.877±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (+/-)-3-(t-butyldimethylsilyloxy)-4,5-hexadien-1-ol 在 palladium dichloride magnesium sulfate 、 原乙酸三乙酯 、 pyridinium chlorochromate 、 methyloxirane 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (+/-)-(2'R,3'S,5'R)-methyl 2-(5'-methoxy-3'-(tert-butyldimethylsilyloxy)-tetrahydrofuran-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：

  (+/-)-6-(4'-methoxyphenylmethoxy)-4-(t-butyldimethylsilyloxy)-1,2-hexadiene 在 pH 7 buffer 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到(+/-)-3-(t-butyldimethylsilyloxy)-4,5-hexadien-1-ol
  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

• Diastereoselective Cobalt-mediated Acylation-Cyclization of Allenes
  作者：Roderick W. Bates、Vachiraporn Satcharoen

  DOI：10.1055/s-2001-12335

  日期：——

  Allenes with α-oxygen and γ-sulfonamide substituents were synthesized and cyclized to pyrrolidines using an acyl cobalt reagent. The reactions proceeded with very high trans selectivity.

  合成具有α-氧和γ-磺酰胺取代基的丙二烯，并使用酰基钴试剂环化为吡咯烷。反应以非常高的反式选择性进行。