3-hydroxy-2,2-dimethyl-3-phenylpropanal | 88903-20-2

• 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: 3-hydroxy-2,2-dimethyl-3-phenylpropanal
• 英文别名: 3-hydroxy-2,2-dimethyl-3-phenyl-propionaldehyde
• CAS: 88903-20-2
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: UVRWUYAKBXOLRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxy-2,2-dimethyl-3-phenylpropanal 在 甲醇 作用下， 生成 3-(1,3-dihydroxy-2,2-dimethyl-3-phenyl-propoxy)-2,2-dimethyl-3-phenyl-propionaldehyde
  参考文献：
  名称：

  Spaeth; Lorenz; Altmann, Chemische Berichte, 1943, vol. 76, p. 513,517

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 150.0~160.0 ℃ 、1.6 kPa 条件下， 生成 3-hydroxy-2,2-dimethyl-3-phenylpropanal
  参考文献：
  名称：

  Spaeth; Lorenz; Altmann, Chemische Berichte, 1943, vol. 76, p. 513,517

  摘要：

  DOI：

文献信息

• One-pot enol silane formation-Mukaiyama aldol reactions: Crossed aldehyde-aldehyde coupling, thioester substrates, and reactions in ester solvents
  作者：C. Wade Downey、Grant J. Dixon、Jared A. Ingersoll、Claire N. Fuller、Kenneth W. MacCormac、Anna Takashima、Rohina Sediqui

  DOI：10.1016/j.tetlet.2019.151192

  日期：2019.10

  Trimethylsilyl trifluoromethanesulfonate (TMSOTf) and a trialkylamine base promote both in situ enol silane/silyl ketene acetal formation and Mukaiyama aldol addition reactions between a variety of reaction partners in a single reaction flask. Isolation of the required enol silane or silyl ketene acetal is not necessary. For example, crossed aldol reactions between α-disubstituted aldehydes and non-enolizable

  三甲基甲硅烷基三氟甲磺酸盐（TMSOTf）和三烷基胺碱可在单个反应瓶中促进原位烯醇硅烷/甲硅烷基烯酮缩醛的形成和Mukaiyama aldol加成反应。不需要分离所需的烯醇硅烷或甲硅烷基烯酮缩醛。例如，α-二取代的醛与不可烯化的醛之间的交叉醇醛缩合反应以良好的产率产生β-羟基醛。在相关的反应中，普通的实验室溶剂乙酸乙酯既充当烯醇化物前体又充当绿色反应溶剂。当使用硫酯作为烯醇化物前体时，常规观察到高产率地加成到不可烯化的醛中。
• Germanium(II)-Mediated Reductive Cross-Aldol Reaction of Aldehydes: Synthesis of Aldols with Diastereocontrolled Quaternary Carbon Centers
  作者：Akio Baba、Shin-ya Tanaka、Makoto Yasuda

  DOI：10.1055/s-2007-982560

  日期：2007.7

  anti-Selective synthesis of aldols with quaternary carbon centers was achieved by germanium(II)-mediated reductive cross-aldol reaction of tertiary α-bromo aldehydes with both aromatic and aliphatic aldehydes. One-pot direct reduction and reductive amination of the aldol products were performed to give the corresponding 1,3-diol and 1,3-amino alcohol with stereocontrolled quaternary carbon centers

  通过锗（II）介导的叔α-溴醛与芳香醛和脂肪醛的还原交叉醛醇反应，实现了具有季碳中心的羟醛的抗选择性合成。对羟醛产物进行一锅直接还原和还原胺化，得到相应的具有立体控制的季碳中心的 1,3-二醇和 1,3-氨基醇。
• ALDEHYDE ENOLATE. CROSS ALDOL REACTION via TIN(II) ENOLATE
  作者：Jun-ichi Kato、Teruaki Mukaiyama

  DOI：10.1246/cl.1983.1727

  日期：1983.11.5

  Tin(II) enolate, formed in situ by the oxidative addition of metallic tin to 2-bromo-2-methylpropanal, reacts with aldehydes to give β-hydroxy aldehydes in fairly good yields.

  烯醇锡 (II) 是通过将金属锡氧化加成到 2-溴-2-甲基丙醛中而原位形成的，与醛反应以相当好的产率得到 β-羟基醛。
• Kohler, Boris A. B., Synthetic Communications, 1985, vol. 15, p. 39 - 42
  作者：Kohler, Boris A. B.

  DOI：——

  日期：——
• Biheteroaromatic diphosphine oxides-catalyzed stereoselective direct aldol reactions
  作者：Sergio Rossi、Maurizio Benaglia、Andrea Genoni、Tiziana Benincori、Giuseppe Celentano

  DOI：10.1016/j.tet.2010.11.009

  日期：2011.1

  A highly stereoselective direct aldol condensation of ketones to aromatic aldehydes was realized; the trichlorosilyl enolether generated in situ in the presence of tetrachlorosilane is activated by catalytic amounts of an enantiomerically pure biheteroaromatic phosphine oxide to react with aldehydes, coordinated as well as activated by the chiral cationic hypervalent silicon species. This Lewis acid-mediated Lewis base-catalyzed transformation allowed, starting from two carbonyl compounds, to directly synthesize beta-hydroxy ketones generally with high anti stereoselectivity and up to 93% ee for the anti isomer. (C) 2010 Elsevier Ltd. All rights reserved.