(E)-2-(1-hydroxy-3-phenylallyl)cyclohexanone | 130751-64-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-2-(1-hydroxy-3-phenylallyl)cyclohexanone
• 英文别名: 2-[(E)-1-hydroxy-3-phenylprop-2-enyl]cyclohexan-1-one
• CAS: 130751-64-3
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: ZSGZMLCCTRDMNL-ZHACJKMWSA-N

物化性质

• 沸点：
  407.7±25.0 °C(predicted)
• 密度：
  1.123±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  反式肉桂醛 、 1-trichloroacetoxycyclohexene 在 二丁基二甲氧基锡 甲醇 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以93%的产率得到(E)-2-(1-hydroxy-3-phenylallyl)cyclohexanone
  参考文献：
  名称：

  二甲基二丁基锡催化烯醇三氯乙酸酯的醛醇缩合反应

  摘要：

  使用二甲基二丁基锡作为新型催化剂，在由THF和MeOH组成的混合溶剂中，实现醛与烯醇三氯乙酸酯的醛醇缩合催化缩合反应。以高达99％的高收率非对映选择性地获得了各种β-羟基酮。

  DOI：

  10.1016/s0040-4039(03)01840-9

文献信息

• Reactive barium-promoted Reformatsky-type reaction of α-chloroketones with aldehydes
  作者：Akira Yanagisawa、Hiroshi Takahashi、Takayoshi Arai

  DOI：10.1039/b314752p

  日期：——

  A Reformatsky-type aldol reaction of α-chloroketones with aldehydes has been achieved using reactive barium as a low-valent metal in THF; this one-pot process is more effective for obtaining the desired β-hydroxy ketones in high yields than the stepwise process in which barium enolates are prepared prior to the reaction with aldehydes.

  使用活性钡作为低价金属，在THF中实现了α-氯代酮与醛的Reformatsky型羟醛反应；这种一步法过程比先制备钡烯醇盐再与醛反应的分步过程更有效地以高产率获得所需的β-羟基酮。
• Dipeptide-catalyzed direct asymmetric aldol reactions in the presence of water
  作者：Meng Lei、Lanxiang Shi、Gong Li、Shilv Chen、Weihai Fang、Zemei Ge、Tieming Cheng、Runtao Li

  DOI：10.1016/j.tet.2007.05.077

  日期：2007.8

  dipeptide has been discovered and developed as an efficient catalyst for the direct asymmetric aldol reactions of unmodified ketones with various aldehydes including aromatic, aliphatic, heteroaromatic, and unsaturated aldehydes in the presence of water at 0 °C. The resulted methodology and optimal conditions led to the corresponding aldol products with high yields (up to 94%) and good enantioselectivities

  基于l-脯氨酸的二肽已被发现并开发为在0°C的水存在下，未修饰的酮与各种醛（包括芳族，脂肪族，杂芳族和不饱和醛）直接不对称醛醇缩合反应的有效催化剂。所得到的方法学和最佳条件导致相应的醛醇产物具有高产率（高达94％）和良好的对映选择性（高达97％ee）。
• Trimethylsilyl trifltate catalyzed aldol-type reaction of enol silyl ethers and acetals or related compounds
  作者：Shizuaki Murata、Masaaki Suzuki、Ryoji Noyori

  DOI：10.1016/s0040-4020(01)86671-0

  日期：1988.1

  condensation of enol trimethylsllyl ethers with acetals, orthoformate, or 2-acetoxytetrahydrofuran or -pyrans to give the corresponding β-alkoxy carbonyl compounds. Reaction of enol silyl ethers and carboxonium triflate ion-pair intermediates occurs via acyclic transition states and exhibits moderate to high erythro selectivity independent of the geometry (E/Z) of the enol silyl ethers.

  加入或不加入受阻叔胺的三氟甲磺酸三甲基甲硅烷基酯催化烯醇三甲基甲硅烷基醚与缩醛，原甲酸酯或2-乙酰氧基四氢呋喃或-吡喃的定向缩合，得到相应的β-烷氧基羰基化合物。烯醇甲硅烷基醚与三氟甲磺酸钾离子对中间体的反应通过无环过渡态发生，并且表现出中等至高的赤型选择性，而与烯醇甲硅烷基醚的几何形状（E / Z）无关。
• Trimethylsilyl trifluoromethanesulfonate-catalyzed aldol reaction of various aldehydes with silyl enol ethers.
  作者：Chisato MUKAI、Satoshi HASHIZUME、Kazuyoshi NAGAMI、Miyoji HANAOKA

  DOI：10.1248/cpb.38.1509

  日期：——

  The aldol reaction of trimethylsilyl enol ethers (1-3) with various aldehydes in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate was investigated. With benzaldehyde (4) the β-hydroxycarbonyl compounds were obtained in good yields. The effect of a substituent on the benzene ring was also examined. Aliphatic aldehydes (11, 13, and 14) were found not to be suitable substrates for this catalytic aldol reaction. On treatment with tert-butyldimethylsilyl enol ethers (30 and 31) under the same conditions, benzaldehydes (4, 5, 7, 8) yielded the corresponding aldol products with good threo-selectivity.

  在三氟甲磺酸三甲基硅酯的催化量存在下，研究了三甲基硅基烯醇醚（1-3）与各种醛的羟醛反应。与苯甲醛（4）反应时，可以得到产率良好的β-羟基羰基化合物。同时还考察了取代基对苯环的影响。发现脂肪醛（11、13和14）不适宜作为这一催化羟醛反应的底物。在相同条件下与叔丁基二甲基硅基烯醇醚（30和31）反应时，苯甲醛（4、5、7、8）能够产生具有良好苏式选择性的相应羟醛产物。
• Asymmetric Aldol Reaction Catalyzed by a Chiral Phosphine-Silver Complex
  作者：Akira Yanagisawa、Ryoji Miyake、Kazuhiro Yoshida

  DOI：10.1002/ejoc.201402351

  日期：2014.7

  A catalytic asymmetric aldol reaction of alkenyl trihaloacetates or a γ,δ-unsaturated δ-lactone with aldehydes or an α-keto ester was achieved by using a 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl·silver trifluoromethanesulfonate complex as the chiral precatalyst and N,N-diisopropylethylamine as the base precatalyst in the presence of methanol. Optically active α-alkyl β-hydroxy ketones with enantioselectivities

  通过使用 2,2'-双（二苯基膦）-1,1'-联萘·三氟甲磺酸银实现了烯基三卤乙酸酯或 γ,δ-不饱和 δ-内酯与醛或 α-酮酯的催化不对称醛醇反应在甲醇存在下，络合物作为手性预催化剂，N,N-二异丙基乙胺作为碱预催化剂。通过原位生成的手性银烯醇化物，以中等至高产率非对映选择性地获得了对映选择性高达 95% ee 的光学活性 α-烷基 β-羟基酮。