methyl-(2E,4E,6Z,8E)-3-³H3C,7-methyl-9-(2,2,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoate | 187339-59-9

• 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-(2E,4E,6Z,8E)-3-³H3C,7-methyl-9-(2,2,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoate
• 英文别名: methyl (2E,4E,6Z,8E)-7-methyl-9-(2,6,6-trimethylcyclohexen-1-yl)-3-(tritritiomethyl)nona-2,4,6,8-tetraenoate
• CAS: 187339-59-9
• 化学式: C₂₁H₃₀O₂
• 分子量: 320.444
• InChiKey: SREQLAJQLXPNMC-OHZNXELASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl-(2E,4E,6Z,8E)-3-³H3C,7-methyl-9-(2,2,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 [3H]-Alitretinoin
  参考文献：
  名称：

  Synthesis of 9-cis-retinoic acid and C-20-[3H3C]-9-cis-retinoic acid with high specific activity

  摘要：

  The synthesis of 9-cis-retinoic acid starting from 2,2,6-trimethylcyclohexanone is described. The same methodology was extended for the synthesis of deuterium and tritium labeled 9-cis-retinoic acid with high specific activity (73 Ci/mmol). In this methodology, a Grignard reaction was utilized for introducing three tritium atoms simultaneously in the final synthetic steps.

  DOI：

  10.1002/(sici)1099-1344(199701)39:1<1::aid-jlcr939>3.0.co;2-a
• 作为产物：
  描述：

  2,2,6-三甲基环己酮 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 甲酸 、 乙基溴化镁 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 21.75h， 生成 methyl-(2E,4E,6Z,8E)-3-³H3C,7-methyl-9-(2,2,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoate
  参考文献：
  名称：

  Synthesis of 9-cis-retinoic acid and C-20-[3H3C]-9-cis-retinoic acid with high specific activity

  摘要：

  The synthesis of 9-cis-retinoic acid starting from 2,2,6-trimethylcyclohexanone is described. The same methodology was extended for the synthesis of deuterium and tritium labeled 9-cis-retinoic acid with high specific activity (73 Ci/mmol). In this methodology, a Grignard reaction was utilized for introducing three tritium atoms simultaneously in the final synthetic steps.

  DOI：

  10.1002/(sici)1099-1344(199701)39:1<1::aid-jlcr939>3.0.co;2-a

文献信息

• Synthesis of 9-cis-retinoic acid and C-20-[3H3C]-9-cis-retinoic acid with high specific activity
  作者：Praveen K. Tadikonda、James M. Lacy、Michael G. Rigdon、Hector F. DeLuca

  DOI：10.1002/(sici)1099-1344(199701)39:1<1::aid-jlcr939>3.0.co;2-a

  日期：1997.1

  The synthesis of 9-cis-retinoic acid starting from 2,2,6-trimethylcyclohexanone is described. The same methodology was extended for the synthesis of deuterium and tritium labeled 9-cis-retinoic acid with high specific activity (73 Ci/mmol). In this methodology, a Grignard reaction was utilized for introducing three tritium atoms simultaneously in the final synthetic steps.