diethyl 2-(dec-2-ynyl)-malonate | 847925-30-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: diethyl 2-(dec-2-ynyl)-malonate
• 英文别名: Diethyl 2-dec-2-ynylpropanedioate
• CAS: 847925-30-8
• 化学式: C₁₇H₂₈O₄
• 分子量: 296.407
• InChiKey: SVUMUZNQXPNQCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 2-(dec-2-ynyl)-malonate 在 2,2'-联吡啶 、 palladium diacetate 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 48.33h， 生成 3-[1-Acetoxy-oct-(E)-ylidene]-4-vinyl-cyclopentane-1,1-dicarboxylic acid diethyl 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：

  1-bromo-2-decyne 、 丙二酸二乙酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以96%的产率得到diethyl 2-(dec-2-ynyl)-malonate
  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.