[2-[(2Z,6E,10E)-12-hydroxy-2,6,10-trimethyldodeca-2,6,10-trienyl]-4-methoxyphenyl] 2,2-dimethylpropanoate | 223676-66-2

• 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: [2-[(2Z,6E,10E)-12-hydroxy-2,6,10-trimethyldodeca-2,6,10-trienyl]-4-methoxyphenyl] 2,2-dimethylpropanoate
• CAS: 223676-66-2
• 化学式: C₂₇H₄₀O₄
• 分子量: 428.612
• InChiKey: CSRCWQWIWMTZAN-JPUPBGNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  [2-[(2Z,6E,10E)-12-hydroxy-2,6,10-trimethyldodeca-2,6,10-trienyl]-4-methoxyphenyl] 2,2-dimethylpropanoate 在 氢氧化钾 、 hafnium(IV) trifluoromethanesulfonate 、 lithium perchlorate 作用下， 以 甲醇 、 二氯甲烷 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 咪唑 、 4-二甲氨基吡啶 、 aluminum oxide 、 磺酰氯 、 18-冠醚-6 、 四丁基氟化铵 、 sodium hydride 、 二异丁基氢化铝 、 sodium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 xylene 为溶剂， 反应 36.0h， 生成 [2-[(2Z,6E,10E)-12-hydroxy-2,6,10-trimethyldodeca-2,6,10-trienyl]-4-methoxyphenyl] 2,2-dimethylpropanoate
  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.