ethyl (2E,6E,10Z)-12-(2-hydroxy-5-methoxyphenyl)-3,7,11-trimethyldodeca-2,6,10-trienoate | 223676-54-8

• 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: ethyl (2E,6E,10Z)-12-(2-hydroxy-5-methoxyphenyl)-3,7,11-trimethyldodeca-2,6,10-trienoate
• CAS: 223676-54-8
• 化学式: C₂₄H₃₄O₄
• 分子量: 386.532
• InChiKey: FNXLXXRJMOKRRN-QQXIVSBVSA-N

物化性质

• 沸点：
  523.1±50.0 °C(predicted)
• 密度：
  1.027±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2E,6E,10Z)-12-(2-hydroxy-5-methoxyphenyl)-3,7,11-trimethyldodeca-2,6,10-trienoate 在 咪唑 、 4-二甲氨基吡啶 、 hafnium(IV) trifluoromethanesulfonate 、 四丁基氟化铵 、 lithium perchlorate 、 二异丁基氢化铝 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (3E,7E,11Z)-17-Methoxy-4,8,12-trimethyl-bicyclo[12.2.2]octadeca-1(17),3,7,11,14(18),15-hexaen-15-ol
  参考文献：
  名称：

  Synthesis of longithorone B, a sixteen-membered farnesylated p-benzoquinone

  摘要：

  The intramolecular coupling reactions at the C-1position of the 10Z-farnesyl moiety appended at the 2'-position of 4'-methoxy phenol derivatives were examined with the aid of Hf(OTf)(4)and LiClO4. When the phenol was protected with a TBDMS group, meta coupling predominated while para coupling occurred efficiently when protected with a pivaloyl group. The para-coupled product was transformed to longithorone B, recently isolated from a tunicate. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00049-0
• 作为产物：
  描述：

  香叶基丙酮 在 aluminum oxide 、 磺酰氯 、 18-冠醚-6 、 sodium hydride 、 sodium carbonate 作用下， 以 xylene 为溶剂， 反应 36.0h， 生成 ethyl (2E,6E,10Z)-12-(2-hydroxy-5-methoxyphenyl)-3,7,11-trimethyldodeca-2,6,10-trienoate
  参考文献：
  名称：

  Synthesis of longithorone B, a sixteen-membered farnesylated p-benzoquinone

  摘要：

  The intramolecular coupling reactions at the C-1position of the 10Z-farnesyl moiety appended at the 2'-position of 4'-methoxy phenol derivatives were examined with the aid of Hf(OTf)(4)and LiClO4. When the phenol was protected with a TBDMS group, meta coupling predominated while para coupling occurred efficiently when protected with a pivaloyl group. The para-coupled product was transformed to longithorone B, recently isolated from a tunicate. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00049-0

文献信息

• Synthesis of longithorone B, a sixteen-membered farnesylated p-benzoquinone
  作者：Tadahiro Kato、Kentaro Nagae、Masahiro Hoshikawa

  DOI：10.1016/s0040-4039(99)00049-0

  日期：1999.3

  The intramolecular coupling reactions at the C-1position of the 10Z-farnesyl moiety appended at the 2'-position of 4'-methoxy phenol derivatives were examined with the aid of Hf(OTf)(4)and LiClO4. When the phenol was protected with a TBDMS group, meta coupling predominated while para coupling occurred efficiently when protected with a pivaloyl group. The para-coupled product was transformed to longithorone B, recently isolated from a tunicate. (C) 1999 Elsevier Science Ltd. All rights reserved.