2-methyl-2-phenyl-but-3-enal | 4370-87-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methyl-2-phenyl-but-3-enal
• 英文别名: 2-methyl-2-phenyl-3-butenal；Methyl-2 phenyl-2 buten-3 al；2-Methyl-2-phenylbut-3-enal
• CAS: 4370-87-0
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: CGTXALIYUPMUSM-UHFFFAOYSA-N

物化性质

• 沸点：
  105 °C(Press: 16 Torr)
• 密度：
  0.970±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2912299000

反应信息

• 作为产物：
  描述：

  2-甲基-1-苯基-丁-3-烯-1,2-二醇 在 硫酸 作用下， 生成 2-methyl-2-phenyl-but-3-enal
  参考文献：
  名称：

  Dana,G. et al., Bulletin de la Societe Chimique de France, 1974, p. 2089 - 2094

  摘要：

  DOI：

文献信息

• Transition-Metal-Free Formylation of Allylzinc Reagents Leading to α-Quaternary Aldehydes
  作者：Ryosuke Haraguchi、Akinori Kusakabe、Nakaba Mizutani、Shin-ichi Fukuzawa

  DOI：10.1021/acs.orglett.8b00360

  日期：2018.3.16

  The first example of formylation of allylzinc reagents using S-phenyl thioformate is presented. The reaction proceeded under mild conditions without any transition-metal catalyst, forming quaternary carbon centers with reactive functionalities, such as formyl and vinyl groups. Moreover, Barbier-type formylation of an allylic bromide with a sterically demanding thioformate was achieved. As a preliminary

  给出了使用S-苯基硫代甲酸酯对烯丙基锌试剂进行甲酰化的第一个实例。反应在温和条件下进行，没有任何过渡金属催化剂，形成具有反应性官能团（如甲酰基和乙烯基）的季碳中心。此外，实现了烯丙基溴与空间上需要的硫代甲酸酯的Barbier型甲酰化。作为初步结果，使用薄荷醇衍生的手性硫代甲酸酯进行了不对称甲酰化。
• Diversity in the reaction modes of anionic and cationic stannyl reagents: γ-Chloro allylstannanes as a vinyl carbene equivalent, and its application for (±) -bakuchiol synthesis
  作者：Jun Fujiwara、Tadashi Sato

  DOI：10.1016/0022-328x(94)80106-1

  日期：1994.6

  Diversity in the reaction modes of anionic stannyl reagents is demonstrated by synthon representation. A new cationic stannyl reagent, γ-chloro allylstannane, has been developed as a vinyl carbene equivalent, and its utility is demonstrated by (±)-bakuchiol synthesis.

  阴离子苯乙烯试剂的反应模式的多样性通过合成子表示来证明。已开发出一种新的阳离子苯乙烯试剂γ-氯代烯丙基锡烷作为乙烯基卡宾当量，其实用性已通过（±）-幕府酚合成得到证明。
• Diversity in the Lewis acid-induced reaction of aldehydes with γ-substituted allylstannanes depending upon the substituent
  作者：Jun Fujiwara、Masami Watanabe、Tadashi Sato

  DOI：10.1039/c39940000349

  日期：——

  Lewis acid-induced reaction of γ-substituted allylstannanes with aldehydes proceeded at the α-, β- or γ-position, depending upon the nature of the substituents.

  路易斯酸诱导的γ-取代烯丙基锡与醛的反应发生在α、β或γ位，具体取决于取代基的性质。
• Allylic-Type Diindium Reagents. Reactivity toward Electrophiles and Cascade Coupling Reactions with Imines
  作者：Tsunehisa Hirashita、Yousuke Hayashi、Kazuma Mitsui、Shuki Araki

  DOI：10.1021/jo026609v

  日期：2003.2.1

  The allylic-type diindium reagents A and B were prepared from 3-bromo-1-iodopropene (1a) and 4-bromo-2-iodobut-2-ene (1b), respectively, and their reactions with electrophiles were investigated. The diindium reagents A and B were initially reacted with imines and the resulting vinylindium compounds were then treated with organic halides in the presence of Pd(PPh3)(4) to give linear N-aryl and N-tosyl homoallylic amines. Diindium A is stable in a small amount of water in solvent, whereas B is easily protonated to give a crotylindium reagent. The reaction of B with benzaldehyde gives mainly the 1,3- and 1,5-diols via a spontaneous coupling with two molecules of the aldehyde, in contrast to A, which reacts with one molecule of carbonyl compounds to give the vinylindium compounds.
• Deux, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1938, vol. 206, p. 1017
  作者：Deux

  DOI：——

  日期：——