4-hydroxy-4-(pyridin-2-yl)butan-2-one | 6337-41-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-hydroxy-4-(pyridin-2-yl)butan-2-one
• 英文别名: 4-hydroxy-4-(2'-pyridyl)butan-2-one；1-hydroxy-1-(2-pyridyl)-3-butanone；4-hydroxy-4-pyridin-2-yl-butan-2-one；4-hydroxy-4-[2]pyridyl-butan-2-one；4-Hydroxy-4-[2]pyridyl-butan-2-on；4-Hydroxy-4--butanon-(2)；4-hydroxy-4-pyridin-2-ylbutan-2-one
• CAS: 6337-41-3
• 化学式: C₉H₁₁NO₂
• mdl: MFCD00634459
• 分子量: 165.192
• InChiKey: NYKHQRHPWDLZTL-UHFFFAOYSA-N

物化性质

• 熔点：
  75.5-76 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  98-100 °C(Press: 0.4 Torr)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxy-4-(pyridin-2-yl)butan-2-one 以68%的产率得到
  参考文献：
  名称：

  KUCHKOVA, K. I.;POPA, D. P., IZV. AN MSSR. CEP. BIOL. I XIM. N., 1986, N 1, 77-78

  摘要：

  DOI：
• 作为产物：
  描述：

  1-pyridin-2-yl-butane-1,3-dione 在 水 、 溶剂黄146 、 锌 作用下， 生成 4-hydroxy-4-(pyridin-2-yl)butan-2-one
  参考文献：
  名称：

  Micko, Monatshefte fur Chemie, 1896, vol. 17, p. 451

  摘要：

  DOI：

文献信息

• Direct aldol and tandem Mannich reactions in room temperature ammonia solutions
  作者：Lichun Feng、Lijin Xu、Kimhung Lam、Zhongyuan Zhou、C.W. Yip、Albert S.C. Chan

  DOI：10.1016/j.tetlet.2005.10.050

  日期：2005.12

  An economical, simple, and efficient direct aldol reaction via the double activation of both aldehydes and ketones by ammonia has been developed. An unprecedented tandem Mannich reaction was observed when hydroxybenzaldehydes, pyrrole-2-carboxyaldehyde, and indole-3-carboxyaldehyde were employed to afford 2,2-dimethyl-6-aryl-4-pyrilidinones in moderate to good yields.

  已经开发了通过氨对醛和酮的双重活化而进行的经济，简单和有效的直接羟醛反应。当使用羟基苯甲醛，吡咯-2-羧基醛和吲哚-3-羧基醛以中等到良好的收率得到2,2-二甲基-6-芳基-4-吡咯烷酮时，观察到了前所未有的串联曼尼希反应。
• Tandem Catalysis by Lipase in a Vinyl Acetate-Mediated Cross-Aldol Reaction
  作者：Manjeet Kumar、Bhahwal A. Shah、Subhash C. Taneja

  DOI：10.1002/adsc.201000980

  日期：2011.5

  The lipase Novozym435 (0.6% w/w) was used in tandem with organocatalysts in a first vinyl/isopropenyl acetate‐mediated aldol reaction. The reaction was facilitated through the lipase‐catalyzed in situ generation of acetaldehyde/acetone. The important features of the present methodology include the mild and facile reaction conditions, regenerability of the lipase, comparatively high yields and minimal

  脂肪酶Novozym435（0.6％w / w）与乙酸乙烯酯/异丙烯基乙酸酯介导的醛醇缩合反应中的有机催化剂一起使用。该反应通过脂肪酶催化的乙醛/丙酮原位生成而得以促进。本方法的重要特征包括温和且容易的反应条件，脂肪酶的可再生性，相对高的收率和最小的副产物形成。
• Electron deficiency of aldehydes controls the pyrrolidine catalyzed direct cross-aldol reaction of aromatic/heterocyclic aldehydes and ketones in water
  作者：Swapandeep Singh Chimni、Dinesh Mahajan

  DOI：10.1016/j.tet.2005.03.045

  日期：2005.5

  A synthetically useful pyrrolidine catalyzed direct cross-aldol reaction of aromatic/heterocyclic aldehydes with ketones in water affords the aldol addition product in up to 93% yield. Electrophilicity of the aldehydes controls the course of the reaction.

  在水中，芳族/杂环醛与酮的合成上有用的吡咯烷催化的直接羟醛缩合反应以高达93％的产率提供了羟醛加成产物。醛的亲电性控制反应过程。
• A Novel DNA-Catalyzed Aldol Reaction
  作者：Zhiyong Wang、Yingfu Li、Gaojun Sun、Jinmin Fan

  DOI：10.1055/s-2008-1078058

  日期：——

  A novel DNA-catalyzed aldol reaction in water has been developed. This approach will be helpful in learning the role of DNA as a catalyst in the early stage during the development of life on earth.

  开发了一种在水中进行的新型DNA催化的醇缩反应。这一方法将有助于了解DNA作为催化剂在地球生命早期发展阶段的作用。
• Chitosan hydrogel: A green and recyclable biopolymer catalyst for aldol and Knoevenagel reactions
  作者：K. Rajender Reddy、K. Rajgopal、C. Uma Maheswari、M. Lakshmi Kantam

  DOI：10.1039/b610355c

  日期：——

  Chitosan hydrogel is efficiently utilized as an organocatalyst for aldol and Knoevenagel reactions, providing the products in high yields with a high chemoselectivity under biphasic conditions. The catalyst was recovered by simple filtration and reused several times without significant loss of activity.

  壳聚糖水凝胶可作为有机催化剂有效地用于醛醇反应和克诺文纳格尔反应，在双相条件下可提供高产率和高化学选择性的产物。通过简单过滤即可回收催化剂，并可多次重复使用而不会明显丧失活性。