2,2-dimethyl-6-hydroxy-3-heptanone | 139367-18-3

• 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: 2,2-dimethyl-6-hydroxy-3-heptanone
• 英文别名: 6-Hydroxy-2,2-dimethylheptan-3-one
• CAS: 139367-18-3
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: NBIXRMIFERWQGF-UHFFFAOYSA-N

物化性质

• 沸点：
  243.0±23.0 °C(Predicted)
• 密度：
  0.919±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  2,2-dimethyl-6-hydroxy-3-heptanone 在 三乙烯二胺 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 N-[5-(1,1-dimethyl-1-ethyl)-5-hexen-2-oxy]-4-(p-chlorophenyl)thiazole-2(3H)thione
  参考文献：
  名称：

  On the 6-endo Selectivity in 4-Penten-1-oxyl Radical Cyclizations

  摘要：

  Regioselectivities in cyclizations of 4-substituted 4-penten-1-oxyl radicals have been investigated in a combined experimental and computational study (density functional theory). The progressive increase of the 6-endo-trig selectivity along the series of 4-substituents H < CH3 < C(CH3)(3) < C6H5 has been interpreted to originate from a balance between strain and FMO interactions. Torsional strain, which is associated with geometrical changes upon an approach of the reacting entities, is relevant for the 6-endo-trig but not for the 5-exo-trig reactions, as seen, for instance, in selective tetrahydrofuran formation from the 4-penten-1-oxyl radical and its 4-methyl derivative. The preference for tetrahydropyran formation in cyclizations of the 4-tert-butyl and the 4-phenyl-4-penten-1-oxyl radical has been attributed to FMO interactions between the terminal carbon atom of the pi bond and the O-radical center thus favoring the 6-endo-trig reaction on the basis of lower transition state energies.

  DOI：

  10.1021/ja049010g
• 作为产物：
  描述：

  频哪酮 、 methyloxirane 在 lithium perchlorate 、 lithium hexamethyldisilazane 作用下， 生成 2,2-dimethyl-6-hydroxy-3-heptanone
  参考文献：
  名称：

  LiClO 4催化烯酸锂向1,2-环氧化合物的加成反应合成γ-羟基酮

  摘要：

  描述了一种简单，有效，抗立体选择性，高度区域选择性的方法，该方法用于在LiClO 4存在下，通过在无水THF中用衍生自简单酮的烯醇锂直接打开1,2-环氧化物来合成γ-羟基酮。

  DOI：

  10.1016/0040-4039(91)80540-m

文献信息

• Yttrium triflate-catalyzed addition of lithium enolates to 1,2-epoxides. Efficient synthesis of γ-hydroxy ketones
  作者：Paolo Crotti、Valeria Di Bussolo、Lucilla Favero、Franco Macchia、Mauro Pineschi

  DOI：10.1016/s0040-4039(00)78266-9

  日期：1994.8

  A simple, efficient method is described for the synthesis of γ-hydroxy ketones by the direct opening of 1,2-epoxides with lithium enolates derived from simple ketones in anhydrous toluene, in the presence of Y(OTf)3.

  描述了一种简单有效的方法，在Y（OTf）3存在下，通过在无水甲苯中直接衍生自简单酮的烯醇锂与1,2-环氧化物直接合成1,2-环氧化物来合成γ-羟基酮。
• Alkylation of carbonyl compounds in the TiCl4-promoted reaction of trimethylsilyl enol ethers with epoxides
  作者：Gojko Lalić、Željko Petrovski、Danica Galonić、Radomir Matović、Radomir N Saičić

  DOI：10.1016/s0040-4020(00)01028-0

  日期：2001.1

  Titanium tetrachloride promoted reaction of trimethylsilyl enol ethers with ethylene oxide affords homoaldol type products in moderate/good yields. Monosubstituted epoxides react regioselectively: the nucleophilic attack of the enolate occurs at the more substituted position of propene oxide whereas epichlorohydrin reacts at the less substituted end.

  四氯化钛促进的三甲基甲硅烷基烯醇醚与环氧乙烷的反应以中等/良好的收率提供了均醛醇型产物。单取代的环氧化物可进行区域选择性反应：烯醇盐的亲核攻击发生在环氧丙烷取代度较高的位置，而环氧氯丙烷则在取代度较低的末端发生反应。
• 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.
• On the 6-<i>e</i><i>ndo</i> Selectivity in 4-Penten-1-oxyl Radical Cyclizations
  作者：Jens Hartung、Rainer Kneuer、Christian Rummey、Gerhard Bringmann

  DOI：10.1021/ja049010g

  日期：2004.9.1

  Regioselectivities in cyclizations of 4-substituted 4-penten-1-oxyl radicals have been investigated in a combined experimental and computational study (density functional theory). The progressive increase of the 6-endo-trig selectivity along the series of 4-substituents H < CH3 < C(CH3)(3) < C6H5 has been interpreted to originate from a balance between strain and FMO interactions. Torsional strain, which is associated with geometrical changes upon an approach of the reacting entities, is relevant for the 6-endo-trig but not for the 5-exo-trig reactions, as seen, for instance, in selective tetrahydrofuran formation from the 4-penten-1-oxyl radical and its 4-methyl derivative. The preference for tetrahydropyran formation in cyclizations of the 4-tert-butyl and the 4-phenyl-4-penten-1-oxyl radical has been attributed to FMO interactions between the terminal carbon atom of the pi bond and the O-radical center thus favoring the 6-endo-trig reaction on the basis of lower transition state energies.
• Synthesis of γ-hydroxy ketones by LiClO4-catalyzed addition of lithium enolates to 1,2-Epoxides
  作者：Marco Chini、Paolo Crotti、Lucilla Favero、Mauro Pineschi

  DOI：10.1016/0040-4039(91)80540-m

  日期：1991.12

  A simple, efficient, anti-stereoselective, highly regioselective method is described for the synthesis of γ-hydroxy ketones by the direct opening of 1,2-epoxides with lithium enolates derived from simple ketones in anhydrous THF, in the presence of LiClO4.

  描述了一种简单，有效，抗立体选择性，高度区域选择性的方法，该方法用于在LiClO 4存在下，通过在无水THF中用衍生自简单酮的烯醇锂直接打开1,2-环氧化物来合成γ-羟基酮。