4-methyl-5-(5-methylfuran-2-ylmethylene)-5H-furan-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 4-methyl-5-(5-methylfuran-2-ylmethylene)-5H-furan-2-one
• 英文别名: (5Z)-4-methyl-5-[(5-methylfuran-2-yl)methylidene]furan-2-one
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: VEDGTXLASSPECM-POHAHGRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  柠康酸酐 在 哌啶 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 17.0h， 生成 4-methyl-5-(5-methylfuran-2-ylmethylene)-5H-furan-2-one
  参考文献：
  名称：

  A facile chemoenzymatic approach to natural cytotoxic ellipsoidone A and natural ellipsoidone B

  摘要：

  Starting from citraconic anhydride (3) a facile four-step synthesis of deoxyellipsoidone 8 has been reported with 37% overall yield. An elegant six-step access to naturally occurring cytotoxic ellipsoidone A (1) and ellipsoidone B (2) has been reported with good overall yields, via the conversion of itaconic anhydride (9) to the acetoxymethylmaleic anhydride (11), regioselective sodium borohydride reduction of anhydride 11 to acetoxymethylbutyrolactone 12, Knoevenagel condensation of lactone 12 with 5-methylfurfural, selenium dioxide induced oxidation of the formed butenolide 13 and an Amano PS catalyzed deacylation of the formed diacetoxybutenolide 14 as a pathway. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.020

文献信息

• A facile chemoenzymatic approach to natural cytotoxic ellipsoidone A and natural ellipsoidone B
  作者：Sanjib Gogoi、Narshinha P. Argade

  DOI：10.1016/j.tet.2005.12.020

  日期：2006.3

  Starting from citraconic anhydride (3) a facile four-step synthesis of deoxyellipsoidone 8 has been reported with 37% overall yield. An elegant six-step access to naturally occurring cytotoxic ellipsoidone A (1) and ellipsoidone B (2) has been reported with good overall yields, via the conversion of itaconic anhydride (9) to the acetoxymethylmaleic anhydride (11), regioselective sodium borohydride reduction of anhydride 11 to acetoxymethylbutyrolactone 12, Knoevenagel condensation of lactone 12 with 5-methylfurfural, selenium dioxide induced oxidation of the formed butenolide 13 and an Amano PS catalyzed deacylation of the formed diacetoxybutenolide 14 as a pathway. (c) 2005 Elsevier Ltd. All rights reserved.