4,4-二甲基-2-戊烯醛 | 926-37-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4,4-二甲基-2-戊烯醛
• 英文名称: 4,4-dimethyl-2-pentenal
• 英文别名: 4,4-dimethylpent-2-enal；4,4-dimethyl-pent-2-enal
• CAS: 926-37-4
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: JZJVARRPMMVFRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,4-二甲基-2-戊烯醛 、 丙二酸二乙酯 在 哌啶 、 苯甲酸 作用下， 以 苯 为溶剂， 生成
  参考文献：
  名称：

  铜催化的区域发散性1,4-和1,6-共轭甲硅烷基加到二己酸酯中：获得官能化的烯丙基硅烷。

  摘要：

  建立了铜催化的甲硅烷基试剂的区域选择性的1,4-和1,6-共轭加成反应以生成二烯键。通过调节反应中使用的配体，以良好的产率和高的区域选择性获得了各种1，4-和1，6-原甲硅烷基化产物。该协议为合成多取代的官能化烯丙基硅烷提供了一种简单有效的方法。

  DOI：

  10.1039/c9ob01086f
• 作为产物：
  描述：

  4,4-dimethyl-2-penten-1-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 生成 4,4-二甲基-2-戊烯醛
  参考文献：
  名称：

  钴催化的 1,1-二取代丙二烯和醛的区域发散和对映选择性分子间偶联

  摘要：

  开发了一系列用于 1,1-二取代丙二烯和醛的区域发散和对映选择性偶联的新方案，这些方案由易于获得的 Co 络合物促进。这些过程代表了通过手性配体精确控制的具有不同区域选择性的丙二烯和醛的对映选择性氧化环化转化的第一个例子。

  DOI：

  10.1002/anie.202219257

文献信息

• Ethers d'enols β-lithies; synthese d'aldehydes α-ethyleniques
  作者：Lucette Duhamel、Francis Tombret、Yves Mollier

  DOI：10.1016/0022-328x(85)87056-x

  日期：1985.1
• Selective syntheses with organometallics. 7. (Z)-2-Ethoxyvinyllithium: a remarkably stable and synthetically useful 1,2-counterpolarized species
  作者：Kreisler S. Y. Lau、Manfred Schlosser

  DOI：10.1021/jo00402a028

  日期：1978.4
• .gamma.-Alkoxyallylboronates as useful reagents for preparation of differentially protected diol derivatives
  作者：Peter G. M. Wuts、Sean S. Bigelow

  DOI：10.1021/jo00133a059

  日期：1982.6
• Kinetics and Products of the Reactions of OH Radicals with 4,4-Dimethyl-1-pentene and 3,3-Dimethylbutanal at 296 ± 2 K
  作者：Sara M. Aschmann、Janet Arey、Roger Atkinson

  DOI：10.1021/jp101893g

  日期：2010.5.13

  Using a relative rate method, rate constants have been measured for the reactions of OH radicals with 4,4-dimethyl-1-pentene [(CH3)(3)CCH2CH=CH2] and its major reaction product, 3,3-dimethylbutanal [(CH3)(3)CCH2CHO], at 296 +/- 2 K and atmospheric pressure of air. The rate constants obtained were 2.41 x 10(-11) and 2.73 x 10(-11) cm(3) molecule(-1) s(-1) respectively, with estimated uncertainties of +/- 10%. The products identified and quantified by gas chromatography with mass spectrometry and/or flame ionization detection from the 4,4-dimethyl-1-pentene reaction were acrolein [CH2=CHCHO], 3,3-dimethylbutanal, and a molecular weight 112 carbonyl attributed to 4,4-dimethyl-2-pentenal [(CH3)(3)CCH=CHCHP], with formation yields of 2.7 +/- 0.5%, 59 +/- 6%, and 3.4 +/- 0.6%, respectively. Using direct air sampling atmospheric pressure ionization mass spectrometry, additional products of molecular weight 146, 177, and 193 were observed, and on the basis of expected reaction schemes these are attributed to the dihydroxycarbonyl HOCH2C(CH3)(2)CH2C(O)CH2OH, the hydroxynitrates (CH3)(3)CCH2CH(OH)CH2ONO2 and/or (CH3)(3)CCH2CH(ONO2)CH2OH, and the dihydroxynitrate O2NOCH2C(CH3)(2)CH2CH(OH)CH2OH, respectively. The hydroxynitrates were also tentatively identified by gas chromatography, with a summed yield of similar to 15%. Acrolein and 4,4-dimethy1-2-pentenal arise from H-atom abstraction from the three equivalent CH3 groups and the 3-position CH2 group, and the sum of their formation yields (6.1 +/- 0.8%) is expected to be very close to the fraction of the overall reaction proceeding by H-atom abstraction.
• Copper-catalyzed regiodivergent 1,4- and 1,6-conjugate silyl addition to diendioates: access to functionalized allylsilanes
  作者：Tanveer Ahmad、Qi Li、Sheng-Qi Qiu、Jian-Lin Xu、Yun-He Xu、Teck-Peng Loh

  DOI：10.1039/c9ob01086f

  日期：——

  A copper-catalyzed regioselective 1,4- and 1,6-conjugate addition of a silyl reagent to diendioates was established. Various 1,4- and 1,6-protosilylation products were obtained in good yields and with high regioselectivity via tuning the ligands used in the reactions. This protocol has provided a simple and efficient method for the synthesis of multisubstituted functionalized allylsilanes.

  建立了铜催化的甲硅烷基试剂的区域选择性的1,4-和1,6-共轭加成反应以生成二烯键。通过调节反应中使用的配体，以良好的产率和高的区域选择性获得了各种1，4-和1，6-原甲硅烷基化产物。该协议为合成多取代的官能化烯丙基硅烷提供了一种简单有效的方法。