(E)-4-(dec-2'-yn-1'-oxy)-but-2-en-1-ol | 847925-29-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-4-(dec-2'-yn-1'-oxy)-but-2-en-1-ol
• 英文别名: (E)-4-dec-2-ynoxybut-2-en-1-ol
• CAS: 847925-29-5
• 化学式: C₁₄H₂₄O₂
• 分子量: 224.343
• InChiKey: JWNBRDUKVHEWIN-PKNBQFBNSA-N

物化性质

• 沸点：
  338.5±32.0 °C(Predicted)
• 密度：
  0.933±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4-(dec-2'-yn-1'-oxy)-but-2-en-1-ol 在 4-二甲氨基吡啶 、 2,2'-联吡啶 、 palladium diacetate 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 生成 Acetic acid 1-[4-vinyl-dihydro-furan-(3Z)-ylidene]-octyl ester
  参考文献：
  名称：

  Cycloisomerization of 1,6-Enynes Using Acetate as a Nucleophile under Palladium(II) Catalysis

  摘要：

  An efficient method for the synthesis of five-membered carbo- and heterocyclic compounds, including fused rings, was reported using acetate as a nucleophile in the cyclization of 1,6-enynes under palladium(II) catalysis. The reaction is initiated by trans-acetoxypalladation of the alkynes and quenched by either trans- or cis-deacetoxypalladation in the presence of 2,2'-bipyridine as the ligand. An example of the catalytic asymmetric cyclization is presented with moderate enantioselectivity using chiral bisoxazoline ligand.

  DOI：

  10.1021/jo048414o
• 作为产物：
  描述：

  反-2-丁烯-1,4-二醇 、 1-bromo-2-decyne 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以73%的产率得到(E)-4-(dec-2'-yn-1'-oxy)-but-2-en-1-ol
  参考文献：
  名称：

  Cycloisomerization of 1,6-Enynes Using Acetate as a Nucleophile under Palladium(II) Catalysis

  摘要：

  An efficient method for the synthesis of five-membered carbo- and heterocyclic compounds, including fused rings, was reported using acetate as a nucleophile in the cyclization of 1,6-enynes under palladium(II) catalysis. The reaction is initiated by trans-acetoxypalladation of the alkynes and quenched by either trans- or cis-deacetoxypalladation in the presence of 2,2'-bipyridine as the ligand. An example of the catalytic asymmetric cyclization is presented with moderate enantioselectivity using chiral bisoxazoline ligand.

  DOI：

  10.1021/jo048414o

文献信息

• Cycloisomerization of 1,6-Enynes Using Acetate as a Nucleophile under Palladium(II) Catalysis
  作者：Qinghai Zhang、Wei Xu、Xiyan Lu

  DOI：10.1021/jo048414o

  日期：2005.2.1

  An efficient method for the synthesis of five-membered carbo- and heterocyclic compounds, including fused rings, was reported using acetate as a nucleophile in the cyclization of 1,6-enynes under palladium(II) catalysis. The reaction is initiated by trans-acetoxypalladation of the alkynes and quenched by either trans- or cis-deacetoxypalladation in the presence of 2,2'-bipyridine as the ligand. An example of the catalytic asymmetric cyclization is presented with moderate enantioselectivity using chiral bisoxazoline ligand.