(+/-)-4-(2-methoxyphenyl)-2-methylene-γ-butyrolactone | 177776-72-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+/-)-4-(2-methoxyphenyl)-2-methylene-γ-butyrolactone
• 英文别名: γ-(2-methoxyphenyl)-α-methylene-γ-butyrolactone；4-(2-methoxyphenyl)-2-methylenebutyrolactone；5-(2-Methoxyphenyl)-3-methylideneoxolan-2-one
• CAS: 177776-72-6
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: MKKYGMJIEHZSAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  propionitrile oxide 、 (+/-)-4-(2-methoxyphenyl)-2-methylene-γ-butyrolactone 以83%的产率得到
  参考文献：
  名称：

  Pereira Suzanne M., Savage G. Paul, Simpson Gregory W., Greenwood Richard+, Austral. J. Chem, 46 (1993) N 9, S 1401-1412

  摘要：

  DOI：
• 作为产物：
  描述：

  邻甲氧基苯甲醛 在 增效醚 、 氯化铵 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 20.0h， 生成 (+/-)-4-(2-methoxyphenyl)-2-methylene-γ-butyrolactone
  参考文献：
  名称：

  铅促进的 2-Carboethoxyallylation 或 2-Carboxylallylation 醛：一种新的和简便的合成 α-亚甲基-γ-丁内酯的方法

  摘要：

  摘要 在铅粉存在下，醛类与α-溴甲基丙烯酸酯（或α-溴甲基丙烯酸）反应可在温和条件下进行，产物4-羟基-2-亚甲基丁酸酯（或4-羟基-2-亚甲基丁酸） ) 在 CF3COOH 存在下可以很容易地转化为 α-亚甲基-γ-丁内酯。

  DOI：

  10.1080/00397919608004550

文献信息

• Lead-Promoted 2-Carboethoxyallylation or 2-Carboxylallylation of Aldehydes: A New and Facile Method for the Synthesis of α-Methylene-γ-Butyrolactones
  作者：Jing-Yao Zhou、Yu Jia、Xu-Bo Yao、Shi-Hui Wu

  DOI：10.1080/00397919608004550

  日期：1996.6

  (or α-bromomethylacrylic acid) can be carried out under mild condition, the products 4-hydroxy-2-methylenebutanoates (or 4-hydroxy-2-methylenebutanoic acids) can be easily converted to α-methylene-γ-butyrolactones in the presence of CF3COOH.

  摘要 在铅粉存在下，醛类与α-溴甲基丙烯酸酯（或α-溴甲基丙烯酸）反应可在温和条件下进行，产物4-羟基-2-亚甲基丁酸酯（或4-羟基-2-亚甲基丁酸） ) 在 CF3COOH 存在下可以很容易地转化为 α-亚甲基-γ-丁内酯。
• Enantioselective Dreiding-Schmidt reactions: asymmetric synthesis and analysis of α-methylene-γ-butyrolactones
  作者：René Csuk、Christina Schröder、Sonja Hutter、Kristina Mohr

  DOI：10.1016/s0957-4166(97)00166-3

  日期：1997.5

  The zinc/silver-graphite mediated Dreiding-Schmidt reactions between aldehydes and the 2-bromomethyl-acrylate derived sultamamides (+)/(-)-28 or (+)/(-)-30 gave the corresponding substituted alpha-methylene-gamma-butyrolactones with ee's up to 90%. Enantiomerically pure compounds were obtained by semipreparative HPLC using a chiral stationary phase. (C) 1997 Elsevier Science Ltd.
• Pereira, Suzanne M.; Savage, G. Paul; Simpson, Gregory W., Australian Journal of Chemistry, 1993, vol. 46, # 9, p. 1401 - 1412
  作者：Pereira, Suzanne M.、Savage, G. Paul、Simpson, Gregory W.、Greenwood, Richard J.、Mackay, Maureen F.

  DOI：——

  日期：——
• Pereira Suzanne M., Savage G. Paul, Simpson Gregory W., Greenwood Richard+, Austral. J. Chem, 46 (1993) N 9, S 1401-1412
  作者：Pereira Suzanne M., Savage G. Paul, Simpson Gregory W., Greenwood Richard+

  DOI：——

  日期：——
• 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.