ethyl (2E,4E)-4-ethyl-2,4-heptadienoate | 128252-13-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (2E,4E)-4-ethyl-2,4-heptadienoate
• 英文别名: ethyl (2E,4E)-4-ethylhepta-2,4-dienoate
• CAS: 128252-13-1
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: KUOUIKORTQMEOC-DGLUDJRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  ethyl (2E,4E)-4-ethyl-2,4-heptadienoate 在 吡啶 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 肼 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-((2E,4E)-4-Ethyl-hepta-2,4-dienyl)-acetamide
  参考文献：
  名称：

  New reagents for controlled release of nitric oxide. Structure-stability relationships

  摘要：

  The synthesis and structure-stability relationships of a series of novel FK409 derivatives (1, 2, and 3) are described. The rates of decomposition in aqueous solution (pH 8.0, 30 degrees C) were parallel with those of spontaneous NO release measured by ESR spectroscopy using carboxy-PTIO. The compounds can cover a wide range of NO releasing rates by appropriate modification of the molecule.

  DOI：

  10.1016/0960-894x(95)00547-7
• 作为产物：
  描述：

  磷酰基乙酸三乙酯 、 (E)-2-ethylpent-2-enal 在 sodium hydride 作用下， 生成 ethyl (2E,4E)-4-ethyl-2,4-heptadienoate
  参考文献：
  名称：

  New reagents for controlled release of nitric oxide. Structure-stability relationships

  摘要：

  The synthesis and structure-stability relationships of a series of novel FK409 derivatives (1, 2, and 3) are described. The rates of decomposition in aqueous solution (pH 8.0, 30 degrees C) were parallel with those of spontaneous NO release measured by ESR spectroscopy using carboxy-PTIO. The compounds can cover a wide range of NO releasing rates by appropriate modification of the molecule.

  DOI：

  10.1016/0960-894x(95)00547-7

文献信息

• Stereoselective Synthesis of Conjugated 2,4-Alkadienoates via the Palladium-Catalyzed Cross-Coupling of 1-Alkenylboronates with 3-Bromo-2-alkenoates
  作者：Teiji Yanagi、Takayuki Oh-e、Norio Miyaura、Akira Suzuki

  DOI：10.1246/bcsj.62.3892

  日期：1989.12

  (2E,4E)-, (2Z,4E)-, and (2E,4Z)-2,4-Alkadienoates can be synthesized in high yields by the cross-coupling of ethyl (E)-3-bromoacrylate, methyl (E)-3-bromo-2-methylpropenoate, ethyl (Z)-3-bromocrotonate,1-bromo-2-(ethoxycarbonyl)cyclohexene, and 4-bromocoumarin with 2-[(E)-1-alkenyl]-1,3,2-benzodioxaboroles or diisopropyl (Z)-1-hexenylboronate in the presence of 3 mol% of Pd(OAc)2, 6 mol% of PPh3, and 2 equivalents of Na2CO3 or K2CO3 in alcoholic solvents while retaining the original configuration of the double bonds in β-bromo esters and 1-alkenylboronates. Although the coupling reaction with 1-hexenylboronate with (Z)-3-bromoacrylate gave a mixture of ethyl (2Z,4E)- and (2E,4E)-nonadienoates in a ratio of 63 : 37, it was found that the use of bis(diphenylphosphino)ferrocene as a ligand of palladium brought about the stereoselective coupling under mild conditions.

  (2E,4E)-、(2Z,4E)- 和 (2E,4Z)-2,4-烷二烯酸酯可以通过乙基(E)-3-溴丙烯酸酯、甲基(E)-3-溴-2-甲基丙烯酸酯、乙基(Z)-3-溴丙烯酸酯、1-溴-2-(乙氧羰基)环己烯和4-溴香豆素与2-[(E)-1-烯基]-1,3,2-苯并二氧硼烷或二异丙基(Z)-1-己烯基硼酸酯在3摩尔%的Pd(OAc)2、6摩尔%的PPh3和2当量的Na2CO3或K2CO3的存在下，在醇溶剂中交叉耦合合成，且保持β-溴酯和1-烯基硼酸酯中双键的原始构型。尽管1-己烯基硼酸酯与(Z)-3-溴丙烯酸酯的耦合反应生成了63:37比率的乙基(2Z,4E)-和(2E,4E)-九烯酸酯的混合物，但发现使用双(苯基磷)铁烯作为钯的配体在温和条件下能够实现立体选择性耦合。
• YANAGI, TEIJI;OH-E, TAKAYUKI;MIYAURA, NORIO;SUZUKI, AKIRA, BULL. CHEM. SOC. JAP., 62,(1989) N2, C. 3892-3895
  作者：YANAGI, TEIJI、OH-E, TAKAYUKI、MIYAURA, NORIO、SUZUKI, AKIRA

  DOI：——

  日期：——