3,4-Dimethyl-1,3-pentadiene | 14145-47-2

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 3,4-Dimethyl-1,3-pentadiene
• 英文别名: 3,4-dimethylpenta-1,3-diene；3,4-dimethyl-1,3-butadiene；3,4-dimethyl-penta-1,3-diene；3,4-Dimethyl-penta-1,3-dien；1.1.2-Trimethyl-butadien-(1.3)；3,4-Dimethyl-pentadien-(1,3)
• CAS: 14145-47-2
• 化学式: C₇H₁₂
• mdl: MFCD07780439
• 分子量: 96.1723
• InChiKey: KFQWHHUZLDASRR-UHFFFAOYSA-N

物化性质

• 沸点：
  108-108.5 °C(Press: 747 Torr)
• 密度：
  0.7544 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3,4-Dimethyl-1,3-pentadiene 在 platinum(IV) oxide barium dihydroxide 、 氢气 、 sulfur 作用下， 以 乙醇 、 水 、 苯 为溶剂， 生成 4-(2,3,4,6-Tetramethyl-phenyl)-butan-2-on
  参考文献：
  名称：

  Syntheses of γ-Ionone Analogues. III. Diels-Alder Reaction Involving a Mixture of 3, 4-Dimethyl-1, 3-pentadiene and 2, 3-Dimethyl-1, 3-pentadiene, and Some Derivatives from 2-Benzyloxymethyl-4, 5, 6-trimethylcyclohexa-1, 4-dienylmethanal

  摘要：

  DOI：

  10.1246/bcsj.35.45
• 作为产物：
  描述：

  1,1,3-三乙氧基-2,3-二甲基丁烷 在 甲酸 、 potassium tert-butylate 、 水 、 sodium formate 作用下， 以 乙醚 为溶剂， 反应 13.0h， 生成 3,4-Dimethyl-1,3-pentadiene
  参考文献：
  名称：

  Regioselective Synthesis and Diels−Alder Reaction of 3,4-Dimethylpenta-1,3-diene. Conformational Study of Bicyclic Adducts Structures by ¹H NMR (NOESY, ASIS) and Molecular Modeling (MM2, AM1, RHF, and DFT)

  摘要：

  A three-step, regioselective synthesis of 3,4-dimethylpenta-1,3-diene 1 has been developed. The condensation of acetone diethylacetal with ethyl propenyl ether yielded, after hydrolysis of the resulting triethoxy adduct 10, 2,3-dimethyl-2-butenal 7. Wittig reaction of 7 with methylenetriphenylphosphorane afforded desired diene 1 in 31% overall yield, easily scalable to the 10 g level, Diels-Alder reaction of 1 with maleic anhydride in benzene was known to afford a 50:50 mixture of "normal" (2) and "rearranged" (3) adducts. In THF as solvent, 2 has been reproducibly obtained in over 90% yield as a 98:2 mixture with 3. H-1 NMR spectroscopy (NOESY, ASIS) and molecular modeling (MM2, AM1, ab initio) have been used jointly to determine the conformation of 2 and 3, All are consistent with a folded structure of "rearranged" 3. On the other hand, only RHF/6-31G* and B3LYP/6-31G* ab initio models were in agreement with NMR spectroscopy for an extended conformation of adduct 2. In this case, neither MM2 nor AM1 models gave results consistent with NMR: discrepancies as high as 30 degrees were noted for some dihedrals between these models and ab initio ones.

  DOI：

  10.1021/jo991173d

文献信息

• VINYL MIGRATION IN THE OXYTHALLATION OF SOME 1,3-DIENES
  作者：Masashi Murakami、Shinya Nishida

  DOI：10.1246/cl.1981.997

  日期：1981.7.5

  The oxythallation of certain 1,3-dienes with thallium(III) nitrate trihydrate in MeOH–CH2Cl2 at 0–20 °C gave products after vinyl migration. Methyl 1-methylcyclopropyl ketone, obtained in the reaction of 2,3-dimethyl-1,3-butadiene, was presumably derived from a cyclopropylmethyl cation, an intermediate in the vinyl migration.

  某些 1,3-二烯与三水合硝酸铊 (III) 在 MeOH–CH2Cl2 中在 0–20 °C 的氧合生成乙烯基迁移后的产物。在 2,3-二甲基-1,3-丁二烯的反应中获得的甲基 1-甲基环丙基酮可能衍生自环丙基甲基阳离子，这是乙烯基迁移的中间体。
• Construction of sterically congested oxindole derivatives <i>via</i> visible-light-induced radical-coupling
  作者：Yanling Shen、Ning Lei、Cong Lu、Dailin Xi、Xinxin Geng、Pan Tao、Zhishan Su、Ke Zheng

  DOI：10.1039/d1sc05273j

  日期：——

  conjugated dienes and enynes, and a broad array of polyfluoroalkyl iodide and oxindoles), which enables modular modification of complex drug-like compounds in one chemical step. The success of solar-driven transformation, large-scale synthesis, and the late-stage functionalization of bioactive molecules, as well as promising tumor-suppressing biological activities, highlights the potential for practical applications

  oxindole 支架代表了许多天然产物和药物相关分子的重要结构特征。在此，我们报告了一种用于合成复杂的 3,3'-二取代 oxindole 衍生物的可见光诱导模块化方法。在温和条件下（不含金属和光催化剂，> 80 个例子），可以通过催化三组分自由基偶联反应合成有价值的含氟烷基的高度空间拥挤的羟吲哚衍生物库。该策略显示出高官能团耐受性和广泛的底物兼容性（包括各种末端或非末端烯烃、共轭二烯和烯炔，以及各种多氟烷基碘和羟吲哚），从而能够对复杂的类药物化合物进行模块化修饰在一个化学步骤中。太阳能驱动转化、大规模合成和生物活性分子的后期功能化的成功，以及有希望的肿瘤抑制生物活性，突出了该策略的实际应用潜力。包括一系列控制实验、紫外-可见光谱和 DFT 计算在内的机理研究表明，该反应经历了一个连续的两步自由基偶联过程，光敏全氟烷基苄基碘是转化的关键中间体。
• Viktorov; Zubritskii, Russian Journal of Organic Chemistry, 1999, vol. 35, # 12, p. 1755 - 1765
  作者：Viktorov、Zubritskii

  DOI：——

  日期：——
• ——
  作者：N. B. Viktorov、L. M. Zubritskii

  DOI：10.1023/a:1013906827883

  日期：——

  The effect of alkyl substituents in 2-alkylbutadienes on their hydromagnesiation with alkyl-magnesium halides was studied.
• Transition Metal Complex Promoted Rearrangements. The Effect of the Metal and of the Attached Ligands on the Mode of Cleavage of Methylated Bicyclo[1.1.0]butanes
  作者：Paul Gassman、G Meyer、Frank Williams

  DOI：10.1021/ja00777a602

  日期：1972.11