(E)-2-(1-methoxy-1-phenylmethylidene)-4-methyl-γ-butyrolactone | 131067-17-9

• 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: (E)-2-(1-methoxy-1-phenylmethylidene)-4-methyl-γ-butyrolactone
• 英文别名: (3E)-3-(methoxy-phenylmethylidene)-5-methyloxolan-2-one；(3E)-3-[methoxy(phenyl)methylidene]-5-methyloxolan-2-one
• CAS: 131067-17-9
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: AETFKHVTLLPXHE-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-phenylpent-4-yn-2-ol 、 无水氯化铜 生成 (E)-2-(1-methoxy-1-phenylmethylidene)-4-methyl-γ-butyrolactone
  参考文献：
  名称：

  TAMARU, YOSHINAO;HOJO, MAKOTO;YOSHIDA, ZEN-ICHI, J. ORG. CHEM., 56,(1991) N, C. 1099-1105

  摘要：

  DOI：

文献信息

• Palladium(II)-catalyzed carbonylation of 3-buten-1-ols and 3-butyn-1-ols: an efficient synthesis of .gamma.-butyrolactones
  作者：Yoshinao Tamaru、Makoto Hojo、Zenichi Yoshida

  DOI：10.1021/jo00003a036

  日期：1991.2

  Palladium(II)-catalyzed dicarbonylation of 3-buten-1-ols (1) in the presence of propylene oxide and ethyl orthoacetate in methanol-dichloromethane under carbon monoxide at atmospheric pressure afforded alpha-[(methoxycarbonyl)methyl]-gamma-butyrolactones (2) in good yields. This dicarbonylation reaction occurs via stereospecific cis addition. Under similar conditions, 4-(trimethylsilyl)-3-butyn-1-ols (4a and 4b) undergo dicarbonylation to provide cis-dicarbonylated alpha-methylene-gamma-butyrolactones (5a and 5b, respectively). 4-Alkyl-and 4-aryl-3-butyn-1-ols (4c-g), on the other hand, undergo trans alkoxycarbonylation across the triple bond and selectively furnish E tetrasubstituted alpha-methylene-gamma-butyrolactones (6).