1-hydroxybut-3-en-2-one pivalate | 1092971-97-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-hydroxybut-3-en-2-one pivalate
• 英文别名: pivaloyloxymethyl vinyl ketone；2-Oxobut-3-enyl 2,2-dimethylpropanoate
• CAS: 1092971-97-5
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: VTHFSWCEFAMSNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-hydroxybut-3-en-2-one pivalate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 正丁基锂 、 triphenylmethylium hexachloroantimonate(V) 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 4.33h， 生成 C₁₆H₂₂O₃
  参考文献：
  名称：

  An Enantioselective Total Synthetic Approach to (+)-Heptemerone G and (+)-Guanacastepene A from 2-Furyl Methyl Carbinol

  摘要：

  An enantioselective synthesis of the key bicyclic building block for (+)-heptemerone G and (+)-guanacastepene A construction has been accomplished. 2-Furyl methyl carbinol was used as the starting material and (S)-4-hydroxy-2-methylcyclopent-2-en-1-one as the primal optically active intermediate.

  DOI：

  10.1055/s-0033-1338857
• 作为产物：
  描述：

  2-hydroxybut-3-enyl 2,2-dimethyl propanoate 在 Jones reagent 作用下， 生成 1-hydroxybut-3-en-2-one pivalate
  参考文献：
  名称：

  鸟粪和庚烯官能化的水合腈核心的合成方法

  摘要：

  已经从2-甲基环戊-2-en-1-one有效地合成了官能化的水az烯衍生物，该研究的方向是具有生物学意义的二萜类化合物，鸟苷和庚酮的全合成。

  DOI：

  10.1016/j.tetlet.2008.09.082

文献信息

• A convenient preparation of (S)-(−)-4-hydroxy-2-methylcyclopent-2-en-1-one and its application as a chiral synthetic equivalent of 2-methylcyclopent-2-en-1-one in the terpenoid synthesis
  作者：Karol Michalak、Jerzy Wicha

  DOI：10.1016/j.tet.2014.06.006

  日期：2014.8

  from 1-(2-furyl)ethanol using modified Piancatelli rearrangement and enzymatic kinetic resolution of the racemate was developed. An application of O-protected derivatives of 4-hydroxy-2-methylcyclopent-2-en-1-one to terpenoid synthesis through tandem conjugate addition of allyl-metal reagents, enolate trapping, and consecutive Mukaiyama–Michael addition was studied. An optically active azulene derivative

  开发了一种通过修饰的Piancatelli重排和消旋体的酶促动力学拆分从1-（2-呋喃基）乙醇制备（S）-4-羟基-2-甲基环戊-2-烯-1-酮的方法。通过串联共轭添加烯丙基金属试剂，烯醇盐捕集和连续Mukaiyama-Michael加成反应，研究了O-保护的4-羟基-2-甲基环戊-2-烯-1-酮在萜类化合物合成中的应用。有效地合成了可用于类萜合成的旋光性z青烯衍生物。
• A synthetic approach to the functionalized hydroazulene core of guanacastepenes and heptemerenes
  作者：Karol Michalak、Michał Michalak、Jerzy Wicha

  DOI：10.1016/j.tetlet.2008.09.082

  日期：2008.11

  A functionalized hydroazulene derivative has been synthesized efficiently from 2-methylcyclopent-2-en-1-one as a part of a study oriented toward the total synthesis of diterpenoids of biological significance, guanacastepenes, and heptemerones.

  已经从2-甲基环戊-2-en-1-one有效地合成了官能化的水az烯衍生物，该研究的方向是具有生物学意义的二萜类化合物，鸟苷和庚酮的全合成。
• Construction of the Tricyclic 5−7−6 Scaffold of Fungi-Derived Diterpenoids. Total Synthesis of (±)-Heptemerone G and an Approach to Danishefsky’s Intermediate for Guanacastepene A Synthesis
  作者：Karol Michalak、Michał Michalak、Jerzy Wicha

  DOI：10.1021/jo101758t

  日期：2010.12.17

  An efficient and operationally simple synthesis of the neodolestane diterpenoids (±)-heptemerone G and (±)-guanacastepene A is reported. The common tricyclic scaffold (±)-4 was prepared from 2-methylcyclopent-2-en-1-one via 23 isolated intermediates in 5.1% yield. The key features include a novel annulation sequence combining tandem conjugate addition, methylenation, and metathesis reaction and completely

  报道了一种新的高雌烷二萜类化合物（±）-庚二酮G和（±）-胍庚二烯A的有效且操作简单的合成方法。普通的三环支架（±）-4由2-甲基环戊-2-烯-1-酮经23种分离的中间体以5.1％的收率制备。关键特征包括结合串联共轭加成，亚甲基化和易位反应的新型环空序列，以及将偶氮衍生物23完全非对映选择性转化为AB环构件32。饱和反式-azulene烯醇化物38及其α，β-不饱和对应物48的烷基化立体化学被检查了。令人惊讶的是，记录了不同的面部选择性。修改或开发了几种合成方法，包括沃顿型重排的替代方法，温和条件下可差向异构化酮的缩酮化，以及酮通过其动力学烯醇化物的有效烷基化。
• An Enantioselective Total Synthetic Approach to (+)-Heptemerone G and (+)-Guanacastepene A from 2-Furyl Methyl Carbinol
  作者：Jerzy Wicha、Karol Michalak

  DOI：10.1055/s-0033-1338857

  日期：——

  An enantioselective synthesis of the key bicyclic building block for (+)-heptemerone G and (+)-guanacastepene A construction has been accomplished. 2-Furyl methyl carbinol was used as the starting material and (S)-4-hydroxy-2-methylcyclopent-2-en-1-one as the primal optically active intermediate.