1-羟基-4,4-二甲基戊-1-烯-3-酮 | 39245-06-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-羟基-4,4-二甲基戊-1-烯-3-酮
• 英文名称: 4,4-dimethyl-3-oxo-pentanal 1-enol tautomer
• 英文别名: 1-hydroxy-4,4-dimethyl-pent-1-en-3-one；1-Hydroxy-4,4-dimethyl-pent-1-en-3-on；2.2-Dimethyl-penten-(4)-ol-(5)-on-(3)；Oxymethylenpinakolin；1-Hydroxy-4,4-dimethylpent-1-en-3-one
• CAS: 39245-06-2
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: WIAGNCOGJRYSJF-UHFFFAOYSA-N

物化性质

• 沸点：
  53-56 °C(Press: 25 Torr)
• 密度：
  0.968±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  1-羟基-4,4-二甲基戊-1-烯-3-酮 在 硫酸 作用下， 以 四氢呋喃 、 乙醚 、 氨 为溶剂， 生成 (Z)-3-tert-butyl-pent-2-en-4-ynal
  参考文献：
  名称：

  Dehydroannulenes. III. Synthesis and Properties of 1,5,10,14-Tetra-tert-butyl-6,8,15,17-tetrakisdehydro[18]annulene

  摘要：

  为了找出在不显著影响富烯环电子相互作用的条件下，能够为四脱氢[18]富烯体系提供稳定性和溶解性的取代基团，从3-叔丁基-2-戊烯-4-炔醛（III）出发，进行了1,5,10,14-四叔丁基-6,8,15,17-四脱氢[18]富烯（VIII）的合成。研究发现，四叔丁基衍生物（VIII）具有强烈的抗磁环流性质，比四甲基、二甲基、二苯基和四苯基类似物更稳定且溶解度更高。四叔丁基衍生物（VIII）的电子光谱与四甲基四脱氢[18]富烯的光谱密切相关，这表明叔丁基对富烯环的电子扰动较小。

  DOI：

  10.1246/bcsj.49.302
• 作为产物：
  描述：

  频哪酮 在 乙醚 、 sodium amide 作用下， 生成 1-羟基-4,4-二甲基戊-1-烯-3-酮
  参考文献：
  名称：

  The Acylation of Ketones with Esters to Form β-Diketones by the Sodium Amide Method¹

  摘要：

  DOI：

  10.1021/ja01225a034

文献信息

• Improved preparation and new reactions of β -(1-phenylthio) cyclopropyl enones
  作者：Jeffrey H. Byers、Thomas A. Spencer

  DOI：10.1016/s0040-4039(00)89117-0

  日期：1985.1

  β-(1-Phenylthio)cyclopropyl enones can be conveniently prepared via reaction of the lithium salts of α-hydroxymethylene ketones with 1-lithio-1-phenylthiocyclopropane and are converted efficiently by treatment with aqueous acid to γ-keto cyclobutanones and less successfully by thermolysis to -γ-keto phenylthiocyclopentenes.

  β-（1-苯硫基）环丙基烯酮可通过α-羟基亚甲基酮的锂盐与1-lithio-1-苯基硫代环丙烷的反应方便地制备，并通过用含水酸处理有效地转化为γ-酮基环丁酮，但成功率较低。热分解为-γ-酮基苯硫基环戊烯。
• Process for the preparation of 5-acylpyrimidines
  申请人：Bayer Aktiengesellschaft

  公开号：US04713456A1

  公开（公告）日：1987-12-15

  A process for the preparation of a 5-acylpyrimidine of the formula ##STR1## in which R is an organic radical comprising reacting a methyl ketone of the formula R--CO--CH.sub.3 in a first stage with a formylating reagent in the presence of a base to form an enolketone of the formula R--CO--CH.dbd.CH--OR.sup.10 in which R.sup.10 represents hydrogen or a base radical, thereafter reacting the enolketone in 2nd and 3rd stages with formamidine or a formamidine salt, and with an amino-formylating agent, and, in a 4th stage heating to cyclize the compound formed. The end products, some of which are new, are intermediates for making herbicides.

  制备式为 ##STR1## 的5-酰基嘧啶的过程，其中R为有机基团，包括以下步骤：第一阶段，在碱存在下，用甲基酮R-CO-CH.sub.3与甲酰化试剂反应，形成烯酮R-CO-CH.dbd.CH-OR.sup.10，其中R.sup.10代表氢或碱基团；第二和第三阶段，将烯酮与甲酰胺或甲酰胺盐以及氨基甲酰化试剂反应；第四阶段，在加热条件下环化所形成的化合物。其中一些最终产物是制造除草剂的中间体，其中一些是新的。
• Basicity of C-substituted pyrazoles in the gas phase: an experimental (ICR) and theoretical study
  作者：J. L. M. Abboud、P. Cabildo、T. Canada、J. Catalan、R. M. Claramunt、J. L. G. De Paz、J. Elguero、H. Homan、R. Notario

  DOI：10.1021/jo00040a040

  日期：1992.7

  The experimental gas-phase proton affinities (PAs) of 32 N-H and N-methyl pyrazoles have been determined by means of Fourier transform ion cyclotron resonance spectroscopy (FTICR). Together with the previously reported PAs for 12 C-methyl-substituted pyrazoles, they provide a set of 57 data (counting each tautomer separately). The remarkably large spread of PAs, ca. 55 kcal.mol-1, makes this set most suitable for structural analyses. In a few cases, ab initio 6-31G//6-31G protonation energies were calculated and found to be linearly related to the experimental PAs to a very high degree of precision. A simple additive model of substituent effects on PAs (including substitutions at positions 3, 4, and 5) was found to hold, even for very crowded derivatives such as 1,4-dimethyl-3,5-di-tert-butylpyrazole (27). The only significant interaction appears between phenyl groups at positions 3 and 5. The statistically averaged substituent effects on PAs were successfully analyzed in terms of polarizability and field and resonance contributions, according to the Taft-Topsom model. Both positions 3 and 5 behave in a way similar to that of position 2 in the pyridines. From this interesting result it follows that, with the exception of 3-aminopyrazole, the tautomerism of pyrazoles is not very dependent of the nature of the 3(5)-substituent.
• Escale,R. et al., Bulletin de la Societe Chimique de France, 1974, p. 725 - 733
  作者：Escale,R. et al.

  DOI：——

  日期：——
• Improved preparation of .gamma.-ketocyclobutanones
  作者：Janet A. Kaydos、Jeffrey H. Byers、Thomas A. Spencer

  DOI：10.1021/jo00280a048

  日期：1989.9