(7Z)-4-羟基-7-(苯基甲亚基)呋喃并[3,2-e][1,3]苯并二噁唑-8(7H)-酮 | 135383-79-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 中文名称: (7Z)-4-羟基-7-(苯基甲亚基)呋喃并[3,2-e][1,3]苯并二噁唑-8(7H)-酮
• 英文名称: cephalocerone
• 英文别名: (7Z)-7-benzylidene-4-hydroxyfuro[2,3-g][1,3]benzodioxol-8-one
• CAS: 135383-79-8
• 化学式: C₁₆H₁₀O₅
• 分子量: 282.252
• InChiKey: KLYHONUCJQKOKE-SDQBBNPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (7Z)-4-羟基-7-(苯基甲亚基)呋喃并[3,2-e][1,3]苯并二噁唑-8(7H)-酮 以 甲醇 、 乙醚 为溶剂， 反应 2.0h， 生成 cephalocerone 6-methyl ether
  参考文献：
  名称：

  Phytoalexin aurone induced in Cephalocereus senilis liquid suspension culture

  摘要：

  A new aurone, 4,5-methylenedioxy-6-hydoxyaurone, isolated from chitin-treated liquid suspension cultures of Cephalocereus senilis showed antibacterial activity. The structure of the aurone, cephalocerone, was elucidated by chemical and spectroscopic methods.

  DOI：

  10.1016/s0031-9422(00)95189-6
• 作为产物：
  描述：

  L-苯丙氨酸 生成 (7Z)-4-羟基-7-(苯基甲亚基)呋喃并[3,2-e][1,3]苯并二噁唑-8(7H)-酮
  参考文献：
  名称：

  Induction of phenylpropanoid pathway enzymes in elicitor-treated cultures ofCephalocereus senilis

  摘要：

  Treatment of old-man-cactus (Cephalocereus senilis) suspension cultures with chitin elicits synthesis of an aurone phytoalexin, cephalocerone. Elicitor-induced de novo synthesis of cephalocerone was demonstrated by incubating elicited cactus cultures with [H-3]phenylalanine; this resulted in the labelling of five induced phenolic compounds including cephalocerone. Increased extractable activities of the phenylpropanoid pathway enzymes phenylalanine ammonia-lyase (PAL), chalcone synthase (CHS) and chalcone isomerase (CHI) accompanied the synthesis of cephalocerone. CHS and PAL, which are both involved in the biosynthesis of cephalocerone, showed maximum activity at 12 and 24 hr post-elicitation, respectively. CHS and CHI activities catalysing the synthesis and subsequent isomerization of 2',4',6'-trihydroxychalcone were present in the cell cultures, consistent with the formation of cephalocerone via a chalcone with no B-ring substituents.

  DOI：

  10.1016/0031-9422(91)83024-f