5-hydroxy-4,5-dimethyl-hexan-3-one | 59357-20-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-hydroxy-4,5-dimethyl-hexan-3-one
• 英文别名: 5-Hydroxy-4,5-dimethylhexan-3-one
• CAS: 59357-20-9
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: FZISCUNFSMYDMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  5-hydroxy-4,5-dimethyl-hexan-3-one 在 sodium hydroxide 、 双氧水 、 lithium hydride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 36.67h， 生成 (3R*,4S*)-2,3-Dimethylhexan-2,4-diol
  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：

  丙酮 、 3-戊酮 生成 5-hydroxy-4,5-dimethyl-hexan-3-one
  参考文献：
  名称：

  Gaudemar,M., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1974, vol. 278, p. 533 - 535

  摘要：

  DOI：

文献信息

• 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
• A Convenient Preparation and Utilization of Lithium Dialkylamides
  作者：F. Gaudemar-Bardone、M. Gaudemar

  DOI：10.1055/s-1979-28721

  日期：——
• Etude en RMN d'une serie de β-diols diastereoisomeres et des dioxannes-1,3 correspondants
  作者：MM.J.P. Maffrand、P. Maroni

  DOI：10.1016/s0040-4039(01)88654-8

  日期：1969.1
• GAUDEMAR-BARDONE F.; GANDEMAR M., SYNTHESIS, 1979, NO 6, 463-465
  作者：GAUDEMAR-BARDONE F.、 GANDEMAR M.

  DOI：——

  日期：——
• POSITIVE PHOTOSENSITIVE RESIN COMPOSITION AND METHOD FOR FORMING PATTERNS BY USING THE SAME
  申请人：LIU Chi-Ming

  公开号：US20120328799A1

  公开（公告）日：2012-12-27

  A photosensitive resin composition and a method for forming patterns by using the same are disclosed. The photosensitive resin composition comprises a novolac resin (A), an ortho-naphthoquinone diazide sulfonic acid ester (B) and a ketol solvent (C). The novolac resin (A) includes a high-ortho novolac resin (A-1) that has ortho-ortho methylene bonding to all methylene bonding in a ratio of 18% to 25%, and a weight ratio (A-1)/(C) of the high-ortho novolac resin (A-1) to the ketol solvent (C) is 0.1 to 2.0, thereby exhibiting excellent temporal stability and further forming patterns with superior film to thickness uniformity and high resolution.