4-methyl-2,2-diphenyl-4-pentenal | 155934-24-0

• 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: 4-methyl-2,2-diphenyl-4-pentenal
• CAS: 155934-24-0
• 化学式: C₁₈H₁₈O
• 分子量: 250.34
• InChiKey: ZGRJKLXWPRXXNR-UHFFFAOYSA-N

物化性质

• 沸点：
  369.4±11.0 °C(predicted)
• 密度：
  1.024±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-methyl-2,2-diphenyl-4-pentenal 在 lithium aluminium tetrahydride 、 sodium acetate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.25h， 生成 4,4-Diphenyl-1,2,2-trimethylpyrrolidine N-oxide
  参考文献：
  名称：

  Reverse Cope elimination reactions. 1. Mechanism and scope

  摘要：

  N-4-Pentenyl- and N-5-hexenyl-N-methylhydroxylamine cyclized under mild conditions in a reverse Cope elimination reaction to give 1,2-dimethylpyrrolidine N-oxide and 1,2-dimethylpiperidine N-oxide, respectively. The reaction was shown to be concerted and thermodynamically controlled. The scope of this novel cyclization is discussed, and comparisons are made with the closely related and previously reported cyclization of monosubstituted alkenylhydroxylamines to give cyclic hydroxylamines.

  DOI：

  10.1021/jo00123a013
• 作为产物：
  描述：

  4-methyl-2,2-diphenylpent-4-en-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 4-methyl-2,2-diphenyl-4-pentenal
  参考文献：
  名称：

  Fused Furan Construction via an Intramolecular [3+2] Cycloaddition Reaction: Syntheses of 4H-Cyclohepta- and 4H-Cyclopenta[b]furans

  摘要：

  General and efficient syntheses of 4H-cyclohepta- and 4H-cyclopenta[b]furans (4 and 5) have been accomplished employing the intramolecular [3+2] dipolar cycloaddition based fused furan construction strategy. Treatment of the oximes (20 and 29), readily prepared from the carboxylic acid (7 and 23) via a conventional sequence of reactions, with aqueous sodium hypochlorite produced excellent yields of the isoxazolines (21 and 30), which, after alkaline hydrolysis or desilylation, were exposed to the conditions of reductive hydrolysis followed by acid-catalyzed cyclization to give the corresponding fused furans (4 and 5) in good overall yields.

  DOI：

  10.3987/com-93-6623

文献信息

• Addition-versus-Oxygenative Cleavage: Two Contradictory Reactivities in the Reaction of <i>N</i>-Benzyl-4-pentenylamine Catalyzed by Colloidal Nanogold under Aerobic Conditions
  作者：Hiroaki Kitahara、Hidehiro Sakurai

  DOI：10.1246/cl.2012.1328

  日期：2012.10.5

  Gold nanoclusters stabilized by a hydrophilic polymer, poly(N-vinyl-2-pyrrolidone), (Au:PVP) catalyze two contradictory types of the reaction from N-benzyl secondary amines with unactivated alkenes in EtOH under basic conditions. One is an intramolecular addition reaction that also starts from N-sulfonylamine or primary amine as previously reported. The other involves the oxygenative cleavage of alkene, giving the corresponding γ-lactam compound.

  由亲水性聚合物聚（N-乙烯基-2-吡咯烷酮）（Au:PVP）稳定的纳米金簇在碱性条件下催化了 N-苄基仲胺与未活化烯烃在 EtOH 中发生的两种相互矛盾的反应。一种是分子内加成反应，也是从 N-磺胺或伯胺开始，如之前所报道的那样。另一种是烯烃的氧裂解反应，生成相应的 γ-内酰胺化合物。
• Aldehydes as O-Nucleophiles in Cobalt Hydride Hydrogen Atom Transfer Catalysis: Overriding the Innate Somophilicity
  作者：Yi-Chen Nie、Fan Yang、Yu-Hao Li、Rong Zhu

  DOI：10.1021/acs.orglett.3c00131

  日期：2023.2.10

  In metal hydride-catalyzed alkene hydrofunctionalization reactions via hydrogen atom transfer, simple carbonyl groups have been well-recognized as good somophiles at the carbon for C–C bond formation. Here we report an alternative pathway exploring the carbonyl as an O-nucleophile to make new C–O bonds during the CoH-catalyzed oxidative cyclization of alkenyl aldehydes. This reaction provides a rapid

  在通过氢原子转移的金属氢化物催化的烯烃加氢官能化反应中，简单的羰基已被公认为碳上良好的嗜热体，可形成 C-C 键。在这里，我们报告了一种替代途径，探索羰基作为 O-亲核试剂，在 CoH 催化的烯基醛氧化环化过程中形成新的 C-O 键。该反应通过亲核捕获原位形成的氧碳鎓中间体，提供快速、温和、模块化和立体选择性（高达 >20:1）进入饱和 O-杂环。研究人员发现，克服羰基固有嗜碱性的关键是促进有机钴物种的形成并抑制自由基交换。
• Chiral Cyclic Alkyl Amino Carbene (CAAC) Transition-Metal Complexes: Synthesis, Structural Analysis, and Evaluation in Asymmetric Catalysis
  作者：Adrien Madron du Vigné、Nicolai Cramer

  DOI：10.1021/acs.organomet.2c00351

  日期：2022.10.10

  Despite recent advances in the field of cyclic alkyl amino carbenes (CAACs) including a few complementary synthetic strategies affording CAACs with various substitution patterns, the application potential of chiral CAACs to efficiently catalyze asymmetric organometallic transformations remains largely underdeveloped. Herein, we describe a convenient and robust route that incorporates common chiral

  尽管环状烷基氨基卡宾 (CAACs) 领域的最新进展包括一些互补的合成策略，提供具有各种取代模式的 CAACs，但手性 CAACs 在有效催化不对称有机金属转化方面的应用潜力仍然很大程度上未开发。在此，我们描述了一种方便且稳健的路线，该路线包含常见的手性伯胺，允许使用范围广泛的手性 CAAC 前体。以简单的方式获得了与 Cu、Au、Ru、Rh、Ir 和 Pd 相应的过渡金属配合物。通过X射线单晶分析全面收集配合物的空间参数，作为进一步配体设计的信息来源。