3-(Z)-chlorobutylidene-4R-chloromethyl-5R-phenyl-γ-butyrolactone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-(Z)-chlorobutylidene-4R-chloromethyl-5R-phenyl-γ-butyrolactone
• 英文别名: (3Z,4R,5R)-3-(1-chlorobutylidene)-4-(chloromethyl)-5-pentyloxolan-2-one
• 化学式: C₁₄H₂₂Cl₂O₂
• 分子量: 293.233
• InChiKey: KSJAWICFOONZRW-SXXPLBAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-己炔酸 在 4-二甲氨基吡啶 、 二(氰基苯)二氯化钯 、 N,N'-二环己基碳二亚胺 、 lithium chloride 、 copper dichloride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 24.0h， 生成 3-(Z)-chlorobutylidene-4R-chloromethyl-5R-phenyl-γ-butyrolactone
  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

• Stereoselective synthesis of enantiopure β, γ-disubstituted α-alkylideneγ-butyrolactones via A palladium(II) catalyzed cyclization
  作者：Guoxin Zhu、Xiyan Lu

  DOI：10.1016/0957-4166(95)00009-e

  日期：1995.2

  β, γ-disubstituted α-alkylidene-γ-butyrolactones with cis or trans relative configurations were synthesized in both optically active forms from readily available homochiral allylic 2-alkynoates by Pd(II) catalysis in the presence of CuX2 and LiX.

  在CuX 2和LiX的存在下，通过Pd（II）催化，由Pd（II）催化的易于合成的手性均烯丙基2-炔酸酯以光学活性形式合成具有顺式或反式构型的β，γ-二取代α-亚烷基-γ-丁内酯。
• 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.