2-methyl-4-acetoxyhexa-1,5-dien-3-ol | 500757-33-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-methyl-4-acetoxyhexa-1,5-dien-3-ol
• 英文别名: (4-Hydroxy-5-methylhexa-1,5-dien-3-yl) acetate；(4-hydroxy-5-methylhexa-1,5-dien-3-yl) acetate
• CAS: 500757-33-5
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: IFFYVYHGAHYAEM-UHFFFAOYSA-N

物化性质

• 沸点：
  250.3±28.0 °C(Predicted)
• 密度：
  1.008±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-4-acetoxyhexa-1,5-dien-3-ol 在 水 、 氢气 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 trans-2,2-dimethyl-4-(1'-methyl-ethenyl)-5-ethenyl-1,3-dioxolane
  参考文献：
  名称：

  A New Protocol for the Acetoxyallylation of Aldehydes Mediated by Indium in THF

  摘要：

  [GRAPHICS]A new precursor of a formal 1-hydroxy allyl anion is represented by 3-bromo-1-acetoxy-1-propene, which is synthesized by the ZnCl2-catalyzed addition of acetyl bromide to propenal. 3-Bromo-1-acetoxy-1-propene reacts with indium powder in THF to give the corresponding 3-acetoxylated ally indium complex, which regioselectively adds to aldehydes, affording monoprotected 1-en-3,4-diols. Diastereoselectivity mainly depends on the nature of the aldehyde; saturated aldehydes afford anti adducts, whereas the alpha,beta -unsaturated aldehydes preferentially lead to the syn isomers.

  DOI：

  10.1021/ol016315g
• 作为产物：
  描述：

  2-甲基丙烯醛 、 (Z)-3-bromopropenyl acetate 在 indium 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 2-methyl-4-acetoxyhexa-1,5-dien-3-ol
  参考文献：
  名称：

  A New Protocol for the Acetoxyallylation of Aldehydes Mediated by Indium in THF

  摘要：

  [GRAPHICS]A new precursor of a formal 1-hydroxy allyl anion is represented by 3-bromo-1-acetoxy-1-propene, which is synthesized by the ZnCl2-catalyzed addition of acetyl bromide to propenal. 3-Bromo-1-acetoxy-1-propene reacts with indium powder in THF to give the corresponding 3-acetoxylated ally indium complex, which regioselectively adds to aldehydes, affording monoprotected 1-en-3,4-diols. Diastereoselectivity mainly depends on the nature of the aldehyde; saturated aldehydes afford anti adducts, whereas the alpha,beta -unsaturated aldehydes preferentially lead to the syn isomers.

  DOI：

  10.1021/ol016315g

文献信息

• 3-Bromopropenyl Esters in Organic Synthesis:  Indium- and Zinc-Mediated Entries to Alk-1-ene-3,4-diols
  作者：Marco Lombardo、Stefano Morganti、Claudio Trombini

  DOI：10.1021/jo0262457

  日期：2003.2.1

  Metallic indium and zinc readily add to 3-bromopropenyl acetate (5) and benzoate (6) either in THF or in water, affording the corresponding 3-acyloxyallyl organometallic compounds. Nucleophilic addition to aldehydes opens a route to alk-1-ene-3,4-diols 2 in good to excellent yields. Two synthetic protocols were developed, the former involving indium in THF under Grignard conditions and the latter involving zinc in aqueous ammonium chloride under Barbier conditions. The diastereoselectivity, under all the conditions examined, mainly depends on the nature of the carbonyl compound; conjugated aldehydes afford syn adducts 2, while unconjugated aldehydes display the opposite anti stereopreference.
• A New Protocol for the Acetoxyallylation of Aldehydes Mediated by Indium in THF
  作者：Marco Lombardo、Rugiada Girotti、Stefano Morganti、Claudio Trombini

  DOI：10.1021/ol016315g

  日期：2001.9.1

  [GRAPHICS]A new precursor of a formal 1-hydroxy allyl anion is represented by 3-bromo-1-acetoxy-1-propene, which is synthesized by the ZnCl2-catalyzed addition of acetyl bromide to propenal. 3-Bromo-1-acetoxy-1-propene reacts with indium powder in THF to give the corresponding 3-acetoxylated ally indium complex, which regioselectively adds to aldehydes, affording monoprotected 1-en-3,4-diols. Diastereoselectivity mainly depends on the nature of the aldehyde; saturated aldehydes afford anti adducts, whereas the alpha,beta -unsaturated aldehydes preferentially lead to the syn isomers.