9-isopropyl-5-(methoxycarbonyl)-1-methyl-6-[(E)-2-phenylethenyl]heptalene-4-carboxylic acid | 259742-54-6

• 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: 9-isopropyl-5-(methoxycarbonyl)-1-methyl-6-[(E)-2-phenylethenyl]heptalene-4-carboxylic acid
• 英文别名: 1-methoxycarbonyl-5-methyl-10-[(E)-2-phenylethenyl]-7-propan-2-ylheptalene-2-carboxylic acid
• CAS: 259742-54-6
• 化学式: C₂₇H₂₆O₄
• 分子量: 414.501
• InChiKey: SVCVIKUCAUTGLC-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.59
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  9-isopropyl-5-(methoxycarbonyl)-1-methyl-6-[(E)-2-phenylethenyl]heptalene-4-carboxylic acid 在 sodium hydroxide 、 草酰氯 、 二异丁基氢化铝 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 12.25h， 生成 methyl 9-isopropyl-1-methyl-4-[(1E,3E)-4-phenylbuta-1,3-dienyl]-6-[(E)-2-phenylethenyl]heptalene-5-carboxylate
  参考文献：
  名称：

  New Syntheses of Di-π-Substituted Heptalenes

  摘要：

  To study the effect of double-bond shifts (DBS) in different type of heptalenes linked to extended pi- systems, several di-pi-substituted heptalenes were synthesized. 6-[(E)-Styryl]heptalene-dicarboxylate 4 was smoothly converted to 1-(chloromethyl)heptalene-dicarboxylate 5 by treatment with t-BuOK and C2Cl6 in THF at -78 degrees. The one-pot reaction of 5 and P(OEt)(3) in the presence of NaI, followed by Wittig-Horner reaction, afforded the 1,6-di-pi-substitute heptalene 6. The reaction of 6-[(1E,3E)-4-phenylbuta-1,3-dienyl]heptalenes 7 or 15 with t-BuOK and benzaldehyde in THF led to the formation of the 1,6-di-pi-substituted heptalenes 13 or 16, together with transesterification products 14 or 17. The transformation of the MeOCO group at C(4) of 6-[(E)-styryl]heptalene-dicarboxylate 4 to a phenylbuta-1,3-dienyl substituent afforded the 3,6-di-pi-substituted heptalene 21a, which is in thermal equilibrium with its DBS isomer 21b in solution. Oxidation of heptalene 22 with SeO2 in dioxane gave carbaldehyde 23, which was then subjected to a Wittig reaction to give the 6,9-di-pi-substituted heptalene-dicarboxylate 24.

  DOI：

  10.1002/(sici)1522-2675(19991215)82:12<2260::aid-hlca2260>3.0.co;2-z
• 作为产物：
  描述：

  dimethyl 7-isopropyl-5-methyl-10-<(E)-2-phenylethenyl>heptalene-1,2-dicarboxylate 在 lithium hydroxide 、 水 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以99%的产率得到9-isopropyl-5-(methoxycarbonyl)-1-methyl-6-[(E)-2-phenylethenyl]heptalene-4-carboxylic acid
  参考文献：
  名称：

  New Syntheses of Di-π-Substituted Heptalenes

  摘要：

  To study the effect of double-bond shifts (DBS) in different type of heptalenes linked to extended pi- systems, several di-pi-substituted heptalenes were synthesized. 6-[(E)-Styryl]heptalene-dicarboxylate 4 was smoothly converted to 1-(chloromethyl)heptalene-dicarboxylate 5 by treatment with t-BuOK and C2Cl6 in THF at -78 degrees. The one-pot reaction of 5 and P(OEt)(3) in the presence of NaI, followed by Wittig-Horner reaction, afforded the 1,6-di-pi-substitute heptalene 6. The reaction of 6-[(1E,3E)-4-phenylbuta-1,3-dienyl]heptalenes 7 or 15 with t-BuOK and benzaldehyde in THF led to the formation of the 1,6-di-pi-substituted heptalenes 13 or 16, together with transesterification products 14 or 17. The transformation of the MeOCO group at C(4) of 6-[(E)-styryl]heptalene-dicarboxylate 4 to a phenylbuta-1,3-dienyl substituent afforded the 3,6-di-pi-substituted heptalene 21a, which is in thermal equilibrium with its DBS isomer 21b in solution. Oxidation of heptalene 22 with SeO2 in dioxane gave carbaldehyde 23, which was then subjected to a Wittig reaction to give the 6,9-di-pi-substituted heptalene-dicarboxylate 24.

  DOI：

  10.1002/(sici)1522-2675(19991215)82:12<2260::aid-hlca2260>3.0.co;2-z

文献信息

• New Syntheses of Di-π-Substituted Heptalenes
  作者：Jianfeng Song、Hans-Jürgen Hansen

  DOI：10.1002/(sici)1522-2675(19991215)82:12<2260::aid-hlca2260>3.0.co;2-z

  日期：1999.12.15

  To study the effect of double-bond shifts (DBS) in different type of heptalenes linked to extended pi- systems, several di-pi-substituted heptalenes were synthesized. 6-[(E)-Styryl]heptalene-dicarboxylate 4 was smoothly converted to 1-(chloromethyl)heptalene-dicarboxylate 5 by treatment with t-BuOK and C2Cl6 in THF at -78 degrees. The one-pot reaction of 5 and P(OEt)(3) in the presence of NaI, followed by Wittig-Horner reaction, afforded the 1,6-di-pi-substitute heptalene 6. The reaction of 6-[(1E,3E)-4-phenylbuta-1,3-dienyl]heptalenes 7 or 15 with t-BuOK and benzaldehyde in THF led to the formation of the 1,6-di-pi-substituted heptalenes 13 or 16, together with transesterification products 14 or 17. The transformation of the MeOCO group at C(4) of 6-[(E)-styryl]heptalene-dicarboxylate 4 to a phenylbuta-1,3-dienyl substituent afforded the 3,6-di-pi-substituted heptalene 21a, which is in thermal equilibrium with its DBS isomer 21b in solution. Oxidation of heptalene 22 with SeO2 in dioxane gave carbaldehyde 23, which was then subjected to a Wittig reaction to give the 6,9-di-pi-substituted heptalene-dicarboxylate 24.