(1'R)-phenyl 2'-propenyl 2-butynoate | 169131-88-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1'R)-phenyl 2'-propenyl 2-butynoate
• CAS: 169131-88-8
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: YUQLKMIMVOCRKQ-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1'R)-phenyl 2'-propenyl 2-butynoate 在 palladium on activated charcoal ruthenium trichloride 、 sodium periodate 、 二(氰基苯)二氯化钯 、 氢气 、 sodium acetate 、 lithium chloride 、 copper dichloride 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 isohomopilopic acid
  参考文献：
  名称：

  Template effect of Pd(II) in the synthesis of differently substituted enantiopure γ-butyrolactones and its synthetic applications

  摘要：

  Under the catalysis of Pd(II) in the presence of CuX(2) and LiX, 1'-substituted allylic 2-alkynoates undergo stereoselective cyclization affording beta, gamma-disubstituted alpha-alkylidene-gamma-butyrolactones with cis or trans relative configurations. A highly efficient hydrogenation reaction of the cyclization product afforded a trans-alpha, beta-disubstituted-gamma-butyrolactone in quantitative yield with high stereoselectivity. Isohomopilopic acid which can be converted into isopilocarpine was synthesized using this methodology by further transformation.

  DOI：

  10.1016/0957-4166(95)00210-g
• 作为产物：
  描述：

  2-丁炔酸 、 (R)-1-苯基-2-丙烯-1-醇 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (1'R)-phenyl 2'-propenyl 2-butynoate
  参考文献：
  名称：

  Template effect of Pd(II) in the synthesis of differently substituted enantiopure γ-butyrolactones and its synthetic applications

  摘要：

  Under the catalysis of Pd(II) in the presence of CuX(2) and LiX, 1'-substituted allylic 2-alkynoates undergo stereoselective cyclization affording beta, gamma-disubstituted alpha-alkylidene-gamma-butyrolactones with cis or trans relative configurations. A highly efficient hydrogenation reaction of the cyclization product afforded a trans-alpha, beta-disubstituted-gamma-butyrolactone in quantitative yield with high stereoselectivity. Isohomopilopic acid which can be converted into isopilocarpine was synthesized using this methodology by further transformation.

  DOI：

  10.1016/0957-4166(95)00210-g

文献信息

• Template effect of Pd(II) in the synthesis of differently substituted enantiopure γ-butyrolactones and its synthetic applications
  作者：Guoxin Zhu、Xiyan Lu

  DOI：10.1016/0957-4166(95)00210-g

  日期：1995.7

  Under the catalysis of Pd(II) in the presence of CuX(2) and LiX, 1'-substituted allylic 2-alkynoates undergo stereoselective cyclization affording beta, gamma-disubstituted alpha-alkylidene-gamma-butyrolactones with cis or trans relative configurations. A highly efficient hydrogenation reaction of the cyclization product afforded a trans-alpha, beta-disubstituted-gamma-butyrolactone in quantitative yield with high stereoselectivity. Isohomopilopic acid which can be converted into isopilocarpine was synthesized using this methodology by further transformation.