1-hydroxy-1-phenyl-3-hexanone | 54135-69-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-hydroxy-1-phenyl-3-hexanone
• 英文别名: 1-Hydroxy-1-phenylhexan-3-one
• CAS: 54135-69-2
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: VJCSOWWPFKKLMC-UHFFFAOYSA-N

物化性质

• 沸点：
  316.4±22.0 °C(Predicted)
• 密度：
  1.046±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  1-hydroxy-1-phenyl-3-hexanone 、 METHYLTITANIUM TRIISOPROPOXIDE 生成 、
  参考文献：
  名称：

  Ukaji, Yutaka; Kanda, Hiroyasu; Yamamoto, Kouji, Chemistry Letters, 1990, # 4, p. 597 - 600

  摘要：

  DOI：
• 作为产物：
  描述：

  9-phenyl-9-borabicyclo[3.3.1]nonane 在 乙二醇二甲醚溴化镍 、 5,5'-二(三氟甲基)-2,2'-联吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 4.08h， 生成 1-hydroxy-1-phenyl-3-hexanone
  参考文献：
  名称：

  羧酸衍生物与 9-BBN 衍生的 Ate 配合物的催化结合偶联。

  摘要：

  β-硼基羰基化合物是通过乙烯基硼“ate”络合物和酰基氯或酸酐亲电子试剂的镍催化交叉偶联产生的。该反应非常高效，仅需两分钟即可完成，并且可应用于多种基材。

  DOI：

  10.1002/anie.201901927

文献信息

• Crossed Aldol Reaction Using Polymer-bound Lithium Amides
  作者：Atsushi Seki、Youichi Takizawa、Fusae Ishiwata、Masatoshi Asami

  DOI：10.1246/cl.2003.342

  日期：2003.4

  Polymer-bound lithium amides were used in an aldol reaction. The introduction of a spacer between the polymer backbone and the reactive site was important to enhance yields of the aldol products. The polymer-bound reagent was repeatedly used in the same reaction after the conversion to the lithium amide.

  聚合物结合的氨基化锂用于醛醇反应。在聚合物主链和反应位点之间引入间隔基对于提高羟醛产物的产率很重要。在转化为氨基化锂后，聚合物结合的试剂在同一反应中重复使用。
• Lewis Acid-Promoted Cross Aldol Reaction of Aldehydes with Ketones Utilizing 3-Methyl-2-phenyl-2-(2-oxoalkyl)benzothiazolines as an Enolate-Transferring Reagent
  作者：Hidenori Chikashita、Shin-ichiro Tame、Seiji Yamada、Kazuyoshi Itoh

  DOI：10.1246/bcsj.63.497

  日期：1990.2

  The treatment of a variety of 3-methyl-2-phenyl-2-(2-oxoalkyl)benzothiazolines with aldehydes in the presence of 2 equivalents of SnCl4 in dichloromethane at −78°C underwent a carbon–carbon bond cleavage at the 2-position of the benzothiazoline ring releasing an 2-oxoalkyl moiety followed by the concurrent aldol-type reaction with aldehydes to afford the corresponding β-hydroxy ketones. Among the Lewis acids examined, SnCl4 was found to be most effective, while a similar reaction employing trimethylsilyl trifluoromethanesulfonate as an electrophilic promoter mainly gave the corresponding aldol-condensation product. In the case of the reaction with 3-methyl-2-phenyl-2-(1-substituted 2-oxoalkyl)benzothiazolines, a diastereomeric mixture of α-substituted β-hydroxy ketones as cross aldol products was obtained and the anti preference was generally observed for reactions with the benzothiazolines possessing an aromatic ketone moiety in modest to poor selectivity ranging between 69:31 and 57:43. In contrast to this, the reaction of the benzothiazoline possessing an alkyl ketone moiety, 3-methyl-2-phenyl-2-(1-methyl-2-oxobutyl)benzothiazoline, with benzaldehyde showed syn preference in modest selectivity of 70:30.

  将多种3-甲基-2-苯基-2-(2-氧烷基)苯并噻唑啉与醛在氯仿中于-78°C存在2当量的SnCl4的条件下反应时，发生了苯并噻唑啉环2位的碳-碳键断裂，释放出2-氧烷基基团，随后与醛发生了同时的醛醇型反应，从而生成相应的β-羟基酮。在考察的路易斯酸中，SnCl4被发现是最有效的，而采用三甲基硅基三氟甲磺酸盐作为电亲核促进剂的类似反应主要生成相应的醛缩合产物。在与3-甲基-2-苯基-2-(1-取代2-氧烷基)苯并噻唑啉反应的情况下，获得了作为交叉醛醇产物的α-取代β-羟基酮的对映体混合物，且在与具有芳香酮基团的苯并噻唑啉的反应中一般观察到了反式优先选择性，其选择性在69:31到57:43之间波动。与此相对，具有烷基酮基团的苯并噻唑啉3-甲基-2-苯基-2-(1-甲基-2-氧丁基)苯并噻唑啉与苯甲醛的反应则表现出顺式优先选择性，选择性为70:30。
• Sur les enolates lithies de cetones. Cetolisation mixte univoque et regiospecifique
  作者：Françoise Gaudemar-bardone、Marcel Gaudemar

  DOI：10.1016/s0022-328x(00)91373-1

  日期：1976.1
• Crossed aldol reaction using cross-linked polymer-bound lithium dialkylamide
  作者：Atsushi Seki、Fusae Ishiwata、Youichi Takizawa、Masatoshi Asami

  DOI：10.1016/j.tet.2004.04.026

  日期：2004.5

  Cross-linked polymer-bound lithium dialkylamides were employed in crossed aldol reaction of various carbonyl compounds with aldehydes to afford the corresponding beta-hydroxycarbonyl compounds. The introduction of spacer chains to the polymer-bound lithium dialkylamide between the base moiety and the polystyrene backbone effectively enhanced yields of the desired aldol adducts. Sometimes better yields were obtained by using the polymer-bound reagent having an appropriate spacer-chain with those obtained using lithium diisopropylamide under homogeneous conditions. Repeated use of these polymeric reagents was demonstrated with no loss of efficiency. (C) 2004 Elsevier Ltd. All rights reserved.
• Novel Aldol-type Reaction Utilizing 3-Methyl-2-phenyl-2-(2-oxoalkyl)benzothiazoline as an Enolate Transferring Reagent
  作者：Hidenori Chikashita、Shi-ichiro Tame、Kazuyoshi Itoh

  DOI：10.3987/com-87-4362

  日期：——