methyl (9Z)-8'-oxo-6,8'-diapocaroten-6-oate | 101034-51-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl (9Z)-8'-oxo-6,8'-diapocaroten-6-oate
• 英文别名: Methyl (9Z)-8'-oxo-6,8'-diapo-6-carotenoate；methyl (2E,4Z,6E,8E,10E,12E,14E,16E)-4,8,13,17-tetramethyl-18-oxooctadeca-2,4,6,8,10,12,14,16-octaenoate
• CAS: 101034-51-9
• 化学式: C₂₃H₂₈O₃
• 分子量: 352.474
• InChiKey: JMFNGSBVJBPGQR-IWRWKHRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (9Z)-8'-oxo-6,8'-diapocaroten-6-oate 在 正丁基锂 、 甲酸 作用下， 以 正己烷 、 水 、 苯 为溶剂， 反应 3.0h， 生成 胭脂素
  参考文献：
  名称：

  Synthesis of Bixin and Three Minor Carotenoids from Annatto (Bixa orellana)

  摘要：

  The three apocarotenoids methyl (9Z)-8'-oxo-6,8'-diapocaroten-6-oate (2), methyl (9Z)-10'-oxo-6,10'diapocaroten-6-oate (4). and methyl (9Z)-14'-oxo-6,14'-diapocaroten-6-oate (5), recently isolated from annatto, were synthesized. The key step of all three syntheses was the Wittig reaction of the (Z)-terminus 6 with the phosphonium salts 15, 18, and 24, carrying the polyene chain. Bixin (1) was synthesized from 2 in a Horner-Emmons reaction.

  DOI：

  10.1002/(sici)1522-2675(19990505)82:5<696::aid-hlca696>3.0.co;2-x
• 作为产物：
  描述：

  4,4-dimethoxy-3-methyl-but-2-en-1-yl-triphenylphosphonium chloride 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 191.5h， 生成 methyl (9Z)-8'-oxo-6,8'-diapocaroten-6-oate
  参考文献：
  名称：

  Synthesis of Bixin and Three Minor Carotenoids from Annatto (Bixa orellana)

  摘要：

  The three apocarotenoids methyl (9Z)-8'-oxo-6,8'-diapocaroten-6-oate (2), methyl (9Z)-10'-oxo-6,10'diapocaroten-6-oate (4). and methyl (9Z)-14'-oxo-6,14'-diapocaroten-6-oate (5), recently isolated from annatto, were synthesized. The key step of all three syntheses was the Wittig reaction of the (Z)-terminus 6 with the phosphonium salts 15, 18, and 24, carrying the polyene chain. Bixin (1) was synthesized from 2 in a Horner-Emmons reaction.

  DOI：

  10.1002/(sici)1522-2675(19990505)82:5<696::aid-hlca696>3.0.co;2-x

文献信息

• Synthesis of Bixin and Three Minor Carotenoids from Annatto (Bixa orellana)
  作者：Adrian Häberli、Hanspeter Pfander

  DOI：10.1002/(sici)1522-2675(19990505)82:5<696::aid-hlca696>3.0.co;2-x

  日期：1999.5.5

  The three apocarotenoids methyl (9Z)-8'-oxo-6,8'-diapocaroten-6-oate (2), methyl (9Z)-10'-oxo-6,10'diapocaroten-6-oate (4). and methyl (9Z)-14'-oxo-6,14'-diapocaroten-6-oate (5), recently isolated from annatto, were synthesized. The key step of all three syntheses was the Wittig reaction of the (Z)-terminus 6 with the phosphonium salts 15, 18, and 24, carrying the polyene chain. Bixin (1) was synthesized from 2 in a Horner-Emmons reaction.