3-hydroxy-3-methylpent-4-en-2-one | 55795-29-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hydroxy-3-methylpent-4-en-2-one
• CAS: 55795-29-4
• 化学式: C₆H₁₀O₂
• 分子量: 114.144
• InChiKey: OSPCGCULLCLMGT-UHFFFAOYSA-N

物化性质

• 沸点：
  176.2±20.0 °C(Predicted)
• 密度：
  0.972±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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-3-methylpent-4-en-2-one 在 lithium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 5-Methyl-4-oxo-5-vinyl-4,5-dihydro-furan-2-carboxylic acid
  参考文献：
  名称：

  Analogues of Acifran:  Agonists of the High and Low Affinity Niacin Receptors, GPR109a and GPR109b

  摘要：

  Recently identified GPCRs, GPR109a and GPR109b, the high and low affinity receptors for niacin, may represent good targets for the development of HDL elevating drugs for the treatment of atherosclerosis. Acifran, an agonist of both receptors, has been tested in human subjects, yet until recently very few analogs had been reported. We describe a series of acifran analogs prepared using newly developed synthetic pathways and evaluated as agonists for GPR109a and GPR109b, resulting in identification of compounds with improved activity at these receptors.

  DOI：

  10.1021/jm070022x
• 作为产物：
  描述：

  3-甲基-1-戊烯-4-炔-3-醇 在 1,2-丙二醇 、 二氧化碳 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 120.0 ℃ 、3.0 MPa 条件下， 反应 10.0h， 以56%的产率得到3-hydroxy-3-methylpent-4-en-2-one
  参考文献：
  名称：

  通过邻二醇和炔丙醇进行热力学有利的二氧化碳转化：无金属催化方法

  摘要：

  摘要有机催化是化学固定CO2的一个有前途的领域。本文中，报道了一种简单的无金属化策略，用于从邻二醇，炔丙醇和CO2一锅制备环状碳酸酯和α-羟基酮。在DBU催化的条件下，证明范围广泛的邻二醇和炔丙醇是有效的。提出了一个合理的机制，其中包括在无金属条件下的详细主反应和副反应。

  DOI：

  10.1016/j.cclet.2019.06.030

文献信息

• Thermodynamic favorable CO2 conversion via vicinal diols and propargylic alcohols: A metal-free catalytic method
  作者：Li-Hua Han、Jing-Yuan Li、Qing-Wen Song、Kan Zhang、Qian-Xia Zhang、Xiao-Fang Sun、Ping Liu

  DOI：10.1016/j.cclet.2019.06.030

  日期：2020.2

  promising field in chemical fixation of CO2. Herein, a facile metal-free strategy was reported for the one-pot preparation of cyclic carbonates and α-hydroxy ketones from vicinal diols, propargylic alcohols and CO2. Wide scope of vicinal diols and propargylic alcohols was demonstrated to be efficient under the DBU-catalyzed conditions. A plausible mechanism was proposed, which included detailed main and side

  摘要有机催化是化学固定CO2的一个有前途的领域。本文中，报道了一种简单的无金属化策略，用于从邻二醇，炔丙醇和CO2一锅制备环状碳酸酯和α-羟基酮。在DBU催化的条件下，证明范围广泛的邻二醇和炔丙醇是有效的。提出了一个合理的机制，其中包括在无金属条件下的详细主反应和副反应。
• Synthesis of α-hydroxy ketones by copper(I)-catalyzed hydration of propargylic alcohols: CO2 as a cocatalyst under atmospheric pressure
  作者：Zhi-Hua Zhou、Xiao Zhang、Yong-Fu Huang、Kai-Hong Chen、Liang-Nian He

  DOI：10.1016/s1872-2067(19)63313-9

  日期：2019.9

  ABSTRACT Inexpensive and efficient Cu(I) catalysis is reported for the synthesis of α-hydroxy ketones from propargylic alcohols, CO2, and water via tandem carboxylative cyclization and nucleophilic addition reaction. Notably, hydration of propargylic alcohols can be carried out smoothly under atmospheric CO2 pressure, generating a series of α-hydroxy ketones efficiently and selectively. This strategy

  摘要 据报道，廉价且高效的 Cu(I) 催化可通过串联羧化环化和亲核加成反应从炔丙醇、CO2 和水合成 α-羟基酮。值得注意的是，炔丙醇的水合反应可以在大气 CO2 压力下顺利进行，高效、选择性地生成一系列 α-羟基酮。该策略显示出在温和条件下使用 CO2 作为关键助催化剂制备有价值的 α-羟基酮的巨大潜力。
• Effective Guanidine-Catalyzed Synthesis of Carbonate and Carbamate Derivatives from Propargyl Alcohols in Supercritical Carbon Dioxide
  作者：Nicola Della Ca'、Bartolo Gabriele、Giuseppe Ruffolo、Lucia Veltri、Tito Zanetta、Mirco Costa

  DOI：10.1002/adsc.201000607

  日期：2011.1.10

  The reactions of propargyl alcohols with carbon dioxide in supercritical carbon dioxide or in acetonitrile with gaseous carbon dioxide in the presence of organic bases as catalysts have been examined. Bicyclic guanidines are effective catalysts for the formation of α‐methylene cyclic carbonates under mild reaction conditions. Oxoalkyl carbonates, oxoalkyl carbamates or α‐methyleneoxazolidinones are

  在有机碱作为催化剂存在下，研究了炔丙醇与二氧化碳在超临界二氧化碳中或在乙腈与气态二氧化碳中的反应。双环胍是在温和的反应条件下形成α-亚甲基环状碳酸酯的有效催化剂。碳酸氧烷基酯，氨基甲酸氧代烷基酯或α-亚甲基恶唑烷酮可从炔丙基醇和外部亲核试剂（醇或胺）开始，一步一步获得高收率和良好的选择性，其中双环胍作为催化剂在超临界二氧化碳中使用。在相同反应条件下，丙炔二醇经过重排过程，而不是二氧化碳的插入，而在存在外部亲核试剂的情况下，形成了碳酸氧根，
• Pyrrole annulation onto aldehydes and ketones via palladium-catalyzed reactions
  作者：Barry M. Trost、Ehud Keinan

  DOI：10.1021/jo01302a001

  日期：1980.7
• Analogues of Acifran:  Agonists of the High and Low Affinity Niacin Receptors, GPR109a and GPR109b
  作者：Jae-Kyu Jung、Benjamin R. Johnson、Tracy Duong、Marc Decaire、Jane Uy、Tawfik Gharbaoui、P. Douglas Boatman、Carleton R. Sage、Ruoping Chen、Jeremy G. Richman、Daniel T. Connolly、Graeme Semple

  DOI：10.1021/jm070022x

  日期：2007.4.1

  Recently identified GPCRs, GPR109a and GPR109b, the high and low affinity receptors for niacin, may represent good targets for the development of HDL elevating drugs for the treatment of atherosclerosis. Acifran, an agonist of both receptors, has been tested in human subjects, yet until recently very few analogs had been reported. We describe a series of acifran analogs prepared using newly developed synthetic pathways and evaluated as agonists for GPR109a and GPR109b, resulting in identification of compounds with improved activity at these receptors.