3-hydroxy-2,3-dimethyl-1-phenylbutan-1-one | 112586-65-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hydroxy-2,3-dimethyl-1-phenylbutan-1-one
• CAS: 112586-65-9
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: GEBGXZJOEPZRHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 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：

  3-hydroxy-2,3-dimethyl-1-phenylbutan-1-one 在 lithium hydride 、 四氯化钛 、 锂硼氢 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.67h， 生成 (5R,6R)-4,4,5-Trimethyl-6-phenyl-[1,3,2]dioxaborinane
  参考文献：
  名称：

  The Role of theα-Stereogenic Center in the Control of Stereoselection in the Reduction ofα-Alkyl-β-hydroxy Ketones: A Highly Diastereoselective Protocol for the Synthesis of 1,2-syn-2-Alkyl-1,3-diols

  摘要：

  Accurate investigations on the role played by an alpha-stereogenic center in controlling the reduction of various classes of beta-hydroxy ketones allowed us to set up a general and highly diastereoselective protocol for the synthesis of 2-alkyl-1,3-diols with 1,2-syn relationship. This methodology is based on the conversion of a beta-hydroxy ketone into the corresponding titanium alcoholate that permits us to organize the substrate in a stable and rigid structure, which stereofacially favors attacking hydride ions. The use of THF as solvent makes available a variety of hydride donors that cover a large spectrum of steric demand: the choice of the more appropriate one depends on the conformational stability of the cyclic intermediate. Excellent results are obtained also in the presence of an additional stereogenic center in the beta-position, even if it exerts a concordant or an opposite steric effect with respect to the alpha-substituent.

  DOI：

  10.1002/1521-3765(20000717)6:14<2590::aid-chem2590>3.0.co;2-x
• 作为产物：
  描述：

  2-溴苯丙酮 、 丙酮 在 chromium dichloride 、 lithium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以88%的产率得到3-hydroxy-2,3-dimethyl-1-phenylbutan-1-one
  参考文献：
  名称：

  The Chromium Reformatsky Reaction: Acces to Adjacent Quarternary Centers

  摘要：

  δ-溴酮、-酯和-硝基化合物与二氯化铬和酮发生巴比耶型反应，生成具有一个或两个新的四元中心的动力学交叉醛醇产物。该反应不需要对试剂进行特殊活化，在室温下进行，适合微量制备。巴豆酸盐反应具有高度的区域选择性，可生成 δ 产物。讨论了溶剂的影响。

  DOI：

  10.1055/s-1997-1219

文献信息

• Fukuzawa, Shin-ichi; Tsuruta, Takuya; Fujinami, Tatsuo, Journal of the Chemical Society. Perkin transactions I, 1987, p. 1473 - 1478
  作者：Fukuzawa, Shin-ichi、Tsuruta, Takuya、Fujinami, Tatsuo、Sakai, Shizuyoshi

  DOI：——

  日期：——
• FUKUZAWA, SHIN-ICHI;TSURUTA, TAKUYA;FUJINAMI, TATSUO;SAKAI, SHIZUYOSHI, J. CHEM. SOC. PERKIN TRANS.,(1987) N 7, 1473-1477
  作者：FUKUZAWA, SHIN-ICHI、TSURUTA, TAKUYA、FUJINAMI, TATSUO、SAKAI, SHIZUYOSHI

  DOI：——

  日期：——
• The Role of theα-Stereogenic Center in the Control of Stereoselection in the Reduction ofα-Alkyl-β-hydroxy Ketones: A Highly Diastereoselective Protocol for the Synthesis of 1,2-syn-2-Alkyl-1,3-diols
  作者：Giuseppe Bartoli、Maria C. Bellucci、Marcella Bosco、Renato Dalpozzo、Enrico Marcantoni、Letizia Sambri

  DOI：10.1002/1521-3765(20000717)6:14<2590::aid-chem2590>3.0.co;2-x

  日期：2000.7.17

  Accurate investigations on the role played by an alpha-stereogenic center in controlling the reduction of various classes of beta-hydroxy ketones allowed us to set up a general and highly diastereoselective protocol for the synthesis of 2-alkyl-1,3-diols with 1,2-syn relationship. This methodology is based on the conversion of a beta-hydroxy ketone into the corresponding titanium alcoholate that permits us to organize the substrate in a stable and rigid structure, which stereofacially favors attacking hydride ions. The use of THF as solvent makes available a variety of hydride donors that cover a large spectrum of steric demand: the choice of the more appropriate one depends on the conformational stability of the cyclic intermediate. Excellent results are obtained also in the presence of an additional stereogenic center in the beta-position, even if it exerts a concordant or an opposite steric effect with respect to the alpha-substituent.
• The Chromium Reformatsky Reaction: Acces to Adjacent Quarternary Centers
  作者：Ludger Wessjohann、Harry Wild

  DOI：10.1055/s-1997-1219

  日期：1997.5

  α-Bromo ketones, -esters and -nitriles react with chromium dichloride and ketones in a Barbier-type reaction to yield the kinetic crossed aldol products with one or two new quarternary centers. The reaction does not require special activation of the reagent, proceeds at room temperature and is suitable for microscale preparations. Crotonates react highly regioselective to yield α-products. The influence of solvents is discussed.

  δ-溴酮、-酯和-硝基化合物与二氯化铬和酮发生巴比耶型反应，生成具有一个或两个新的四元中心的动力学交叉醛醇产物。该反应不需要对试剂进行特殊活化，在室温下进行，适合微量制备。巴豆酸盐反应具有高度的区域选择性，可生成 δ 产物。讨论了溶剂的影响。