ethyl 4-methylhexa-2,3-dienoate | 65359-66-2

• 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 4-methylhexa-2,3-dienoate
• 英文别名: racem. 4-Methyl-2,3-hexadiensaeure-ethylester；Ethyl-4-methyl-2,3-hexadienat
• CAS: 65359-66-2
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: NKKCZEGCXRSCSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 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 4-methylhexa-2,3-dienoate 生成 4-Methyl-hexa-2,3-diensaeure
  参考文献：
  名称：

  Runge,W. et al., Justus Liebigs Annalen der Chemie, 1975, p. 1361 - 1378

  摘要：

  DOI：
• 作为产物：
  描述：

  {C5H5(CO)Fe}2(μ-CH3CH2(CH3)CCCHCO2C2H5) 在 氧气 作用下， 以 氘代苯 为溶剂， 以56%的产率得到ethyl 4-methylhexa-2,3-dienoate
  参考文献：
  名称：

  Photochemical reactions of diiron .mu.-alkenylidene complexes with hydrogen, trialkylsilanes, and diazo compounds: cleavage to alkenes, vinylsilanes and allenes

  摘要：

  DOI：

  10.1021/ja00229a025

文献信息

• Investigations on synthesis of indole based constrained mimetic scaffolds through 1,3-dipolar cycloadditions of the C-(3-indolyl)-N-phenylnitrone with a variety of olefinic and allenic dipolarophiles under microwave irradiation
  作者：Surinderjit Singh Bhella、Ajay Pal Singh Pannu、Munusamy Elango、Ashish Kapoor、Maninder Singh Hundal、Mohan Paul S. Ishar

  DOI：10.1016/j.tet.2009.05.093

  日期：2009.8

  3-dipolar cycloadditions of C-(3-indolyl)-N-phenylnitrone (19) with a number of olefinic dipolarophiles (20a–f) afford isoxazolidines (21–26) in high yields, which are conformationally constrained mimetics of indole-3-propionic acid of biological significance. Similar cycloadducts derived from addition of nitrone (19) to allenic esters (27a–c) undergo domino reorganization to afford potentially biologically

  单模微波辅助的区域选择性和立体选择性的1,3-偶极环加成Ç - （3-吲哚基） - ñ -phenylnitrone（19）具有多个烯属dipolarophiles（的20A - ˚F）得到异恶唑烷（21 - 26高）产率，其为具有生物学意义的吲哚-3-丙酸的构象约束模拟物。从另外的硝酮（衍生类似cycloadducts 19），以丙二烯酯（27A - C ^）经历多米诺重组，得到潜在生物活性双吲哚衍生物（28，29）。除其他方面外，根据HOMO-偶极-LUMO-偶极亲和物分析了观察到的区域和立体选择性，并在过渡态介入这些环加成过程中涉及了次级轨道/空间相互作用。
• Regio- and π-Facial Selective Cycloadditions Involving 2-Phenyl-4-dimethylamino-1-thia-3-azabuta-1,3-diene and Allenic Esters: An Efficient Route to Novel 6-Alkylidene-6<i>H</i>-2-phenyl-5-ethoxycarbonyl-1,3-thiazines
  作者：M. P. Ishar、Ashish Kapur、Tilak Raj、Navdeep K. Girdhar、Amritpal Kaur

  DOI：10.1055/s-2004-815995

  日期：——

  2-Phenyl-4-dimethylamino-1-thia-3-azabuta-1,3-diene (4) undergoes regio- and stereoselective [4+2] cycloadditions with allenic esters on refluxing in CH2Cl2-benzene and the initially formed cycloadducts 6 furnish, after elimination of dimethylamine, novel (E/Z)-6-alkylidene-6H-2-phenyl-5-ethoxycarbonyl-1,3-thiazines 7 and 8 in high yields. In the case of reaction with ethyl 2-methylbuta-2,3-dienoate, the adduct 6e has been isolated in very high yields.

  在 CH2Cl2-苯中回流时，2-苯基-4-二甲基氨基-1-噻-3-氮杂-1,3-二烯（4）与异戊烯酯发生区域和立体选择性[4+2]环加成反应，最初形成的环加成物 6 在除去二甲胺后，高产率地生成了新的（E/Z）-6-亚烷基-6H-2-苯基-5-乙氧基羰基-1,3-噻嗪 7 和 8。在与 2-甲基丁-2,3-二烯酸乙酯反应的情况下，以极高的产率分离出了加合物 6e。
• Photoaddition of benzophenone to allenic esters
  作者：M.P.S. Ishar、R.P. Gandhi

  DOI：10.1016/s0040-4020(01)96131-9

  日期：——

  Photochemical addition of benzophenone to ethyl-penta-2, 3-dienoate (), ethyl hexa-2,3-dienoate () and ethyl 4-methylhexa-2,3-dienoate () furnish various mono- and dioxetanes. Novel oxetanes () result in the reactions of () through addition of benzophenone to electron deficient C2-C3 π-bond of the respective esters. A rationalization of the obtained modes of photoaddition has been offered.

  将二苯甲酮光化学加成到戊二酸二乙酯，3-二烯二酸酯（），己二酸2-3,3-二烯酸乙酯（）和4-甲基己二烯丙基-2,3-二烯酸乙酯（）中，提供了各种单氧杂环丁烷和二氧杂环丁烷。新颖的氧杂环丁烷（）导致的（反应）通过添加二苯甲酮，以缺电子的C 2 -C 3的各自的酯的π键。已经提供了获得的光加成模式的合理化。
• Periselectivities in Thermal Addition of Tropone to Allenic Esters
  作者：R. P. Gandhi、M. P. S. Ishar

  DOI：10.1246/cl.1989.101

  日期：1989.1

  Unlike the reactions of tropone with tetraethylallenetetracarboxylic ester and phenylsulphonylpropa-1,2-diene reported in the literature (which yield 2+8 cycloadducts), thermal additions involving tropone and ethyl penta-2,3-dienoate, ethyl hexa-2,3-dienoate and ethyl 4-methylhexa-2,3-dienoate occur predominantly in a 2+4 manner. The reactions are of mechanistic significance.

  与文献中报道的托品酮与四乙基丙二烯四甲酸酯和苯磺酰基丙-1,2-二烯的反应（产生2+8环加合物）不同，热加成涉及托品酮和五-2,3-二烯酸乙酯、乙基六-2,3-二烯酸和4-甲基六-2,3-二烯酸乙酯主要以2+4方式发生。这些反应具有机械意义。
• Acetylenes. Part 2. 2-methylpyrimidin-4(3H)-ones and 4-amino-6-(1-hydroxyalkyl)-2-methylpyrimidines from alka-2,3-dienoates and 4-hydroxyalk-2-ynenitriles, respectively
  作者：Ralph R Roberts、Stephen R Landor、Evon.A Bolessa

  DOI：10.1016/s0040-4039(00)76817-1

  日期：1994.5

  Ethyl alka-2,3-dienoates and 4-tetrahydropyranyloxyalk-2-ynenitriles provide a 3-atom fragment when reacted with acetamidine in tetrahydrofuran, to furnish 2-methylpyrimidin-4(3H)ones and 4-amino-2-methyl-6-(1-tetrahydropyranyloxyalkyl)pyrimidines, respectively (60-70%yield). The latter, with hydrochloric acid / ethanol, gave the corresponding 4-amino-6-(1-hydroxyallcyl-2-merhylpyrimidines as their hydrochloride salts.