dimethyl 7-isopropyl-5-methyl-10-<(E)-2-phenylethenyl>heptalene-1,2-dicarboxylate | 167259-13-4

• 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: dimethyl 7-isopropyl-5-methyl-10-<(E)-2-phenylethenyl>heptalene-1,2-dicarboxylate
• 英文别名: dimethyl 9-isopropyl-1-methyl-6-<(E)-2-phenylethenyl>heptalene-4,5-dicarboxylate；dimethyl 5-methyl-10-[(E)-2-phenylethenyl]-7-propan-2-ylheptalene-1,2-dicarboxylate
• CAS: 167259-13-4
• 化学式: C₂₈H₂₈O₄
• 分子量: 428.528
• InChiKey: ODOMFWYOIKIVNF-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  7-isopropyl-1-methyl-4-<(E)-2-phenylethenyl>azulene 、 丁炔二酸二甲酯 以30%的产率得到
  参考文献：
  名称：

  Briquet Anne Andree Sophie, Hansen HansJuergen, Helv. chim. acta, 77 (1994) N 7, S 1940- 1968

  摘要：

  DOI：

文献信息

• Thermal and Ru-catalyzed Reactions of Styryl-Substituted Azulenes with Dimethyl Acetylenedicarboxylate
  作者：Anne Andr�e Sophie Briquet、Hans-J�rgen Hansen

  DOI：10.1002/hlca.19940770723

  日期：1994.11.2

  are formed, the corresponding benzanellated azulene trans-29 ist found to be the second main product (21 and 10%, respectively) under both reaction conditions. The thermal reaction yields also the benzanellated azulene 28 which is not found in the catalyzed variant of the reaction. Heptalene-1,2-dicarboxylates are also formed from 4-[(E)-styryl]azulenes (e.g. (E)-33 and (E)-34; Scheme 14) and ADM at

  1-[（E）-苯乙烯基] azulenes与十氢化萘中的乙炔二羧酸二甲酯（ADM）在190-200°的热反应不会导致相应的庚烯1,2-二羧酸酯的形成（方案2）。主要产物是相应的薁基-1,2-二羧酸酯（见4和9），并伴有benzanellated薁反式- 10A和反式- 11分别。后者的化合物通过起始天青烯和ADM的Diels - Alder反应，然后与ADM进行烯反应形成（参见方案3）。[RuH 2（PPh 3）4 ]在ACN中于110°催化4,6,8-三甲基-1-[[（E）-4-R-苯乙烯基] azulenes（R = H，MeO，Cl;流程4）与ADM的反应主要成分为1,2-二氮杂ul。但是，在这种情况下，也会少量生成相应的庚烯1,2-二羧酸酯（3-5％；方案4）。所述benzanellated薁反式- 10A和反式-图10b是在反应混合物中少量（2-3％）也有发现。还观察到了少量的（
• Briquet Anne Andree Sophie, Hansen HansJuergen, Helv. chim. acta, 77 (1994) N 7, S 1940- 1968
  作者：Briquet Anne Andree Sophie, Hansen HansJuergen

  DOI：——

  日期：——
• 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.