(E)-4-(pent-1-enyl)-3-phenyl-2-methylenebutyrolactone

• 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)-4-(pent-1-enyl)-3-phenyl-2-methylenebutyrolactone
• 英文别名: 3-methylidene-5-[(E)-pent-1-enyl]-4-phenyloxolan-2-one
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: HHNQDQDQDPVQOP-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-4-(pent-1-enyl)-3-phenyl-2-methylenebutyrolactone
  参考文献：
  名称：

  New antifungal scaffold derived from a natural pharmacophore: Synthesis of α-methylene-γ-butyrolactone derivatives and their antifungal activity against Colletotrichum lagenarium

  摘要：

  Thirty new and thirty-four known analogues were designed and synthesized to improve the potential use of the alpha-methylene-gamma-butyrolactone ring, a natural pharmacophore. All structures were confirmed by H-1 and C-13 NMR, MS, and single-crystal X-ray diffraction analyses. The results of antifungal and cytotoxic activity indicated that the synthesized analogues showed significant inhibitory activity and limited selectivity. Compound 45 exhibited the highest antifungal activity with IC50 = 22.8 mu M but moderate cytotoxic activity with IC50 = 28.5 mu M (against BGC823 cell line) and 7.7 mu M (against HeLa cell line). Analysis of structure-activity relationships revealed that the incorporation of an aromatic ring into the beta, gamma positions of the lactone ring improved antifungal activity, and that the introduction of electron-withdrawing groups into the aromatic rings increased the activity compared with electron-donating groups. The above results identified 4-phenyl-3-phenyl-2-methylenebutyrolactone (33) as a lead scaffold for discovering and developing novel and improved crop-protection agents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.073

文献信息

• Synthesis of 3,4-disubstituted α-methylene-γ-lactones via sonochemical Barbier-type reaction
  作者：Adam Shih-Yuan Lee、Yu-Ting Chang、Shu-Huei Wang、Shu-Fang Chu

  DOI：10.1016/s0040-4039(02)02088-9

  日期：2002.11

  Barbier-type reaction condition and then followed by the in situ intramolecular esterification. The α-methylene-γ-lactone was produced as the sole product when THF/PhH solvent mixture was used whereas the allylation adduct was generated as the major product when solvent DMF was used.

  通过声化学Barbier型反应条件，通过烯丙基溴与醛的加成反应，然后原位分子内酯化，合成了一系列3,4-二取代的α-亚甲基-γ-内酯。当使用THF / PhH溶剂混合物时，α-亚甲基-γ-内酯是唯一的产物，而当使用溶剂DMF时，烯丙基化加合物是主要产物。
• New antifungal scaffold derived from a natural pharmacophore: Synthesis of α-methylene-γ-butyrolactone derivatives and their antifungal activity against Colletotrichum lagenarium
  作者：Feng Jun-Tao、Wang De-Long、Wu Yong-Ling、Yan He、Zhang Xing

  DOI：10.1016/j.bmcl.2013.05.073

  日期：2013.8

  Thirty new and thirty-four known analogues were designed and synthesized to improve the potential use of the alpha-methylene-gamma-butyrolactone ring, a natural pharmacophore. All structures were confirmed by H-1 and C-13 NMR, MS, and single-crystal X-ray diffraction analyses. The results of antifungal and cytotoxic activity indicated that the synthesized analogues showed significant inhibitory activity and limited selectivity. Compound 45 exhibited the highest antifungal activity with IC50 = 22.8 mu M but moderate cytotoxic activity with IC50 = 28.5 mu M (against BGC823 cell line) and 7.7 mu M (against HeLa cell line). Analysis of structure-activity relationships revealed that the incorporation of an aromatic ring into the beta, gamma positions of the lactone ring improved antifungal activity, and that the introduction of electron-withdrawing groups into the aromatic rings increased the activity compared with electron-donating groups. The above results identified 4-phenyl-3-phenyl-2-methylenebutyrolactone (33) as a lead scaffold for discovering and developing novel and improved crop-protection agents. (C) 2013 Elsevier Ltd. All rights reserved.