2-oxa-4-oxo-1-phenylspiro<2,5>octane | 13243-58-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-oxa-4-oxo-1-phenylspiro<2,5>octane
• 英文别名: 2-phenyl-1-oxaspiro[2.5]octan-4-one；(2R,3R)-2-phenyl-1-oxaspiro[2.5]octan-4-one
• CAS: 13243-58-8；34492-12-1；63257-48-7；63257-49-8；63324-00-5；63324-01-6；63324-02-7；63324-03-8；131485-22-8
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: FWNJNJWKMWRQER-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-溴环己酮 、 苯甲醛 在 六甲基磷酰三胺 、 乙基(三丁基锡烷基)氨基甲酸甲酯 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以68%的产率得到2-oxa-4-oxo-1-phenylspiro<2,5>octane
  参考文献：
  名称：

  A Novel Darzens type reaction promoted by tributylstannylcarbamate

  摘要：

  Stannylcarbamate 1 proved to be a selective agent for generating organotin(IV) enolates from alpha-halo ketones. Thus, a Darzens reaction was achieved under mild and neutral conditions. The reaction took place without any side reactions and even with aliphatic alpha-halo ketones bearing enolizable alpha'-hydrogens. Various types of alpha,beta-epoxy ketones and esters were obtained in this one-pot reaction. The stereoselectivity of the reaction was influenced by changing the halogen substituent of the alpha-halo ketones and by additives. Moreover, the present method could be applied to gamma- and delta-halo ketones as enolate precursors, and five- and six-membered cyclic compounds were obtained.

  DOI：

  10.1021/jo00051a043

文献信息

• An efficient Darzens reaction promoted by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)
  作者：Juan Luo、Lanfang Hu、Minghao Zhang、Qiang Tang

  DOI：10.1016/j.tetlet.2019.06.034

  日期：2019.7

  efficient DBU promoted Darzens reaction utilising α-haloketones containing an enolizable α′-hydrogen is reported. This method diastereoselectively afforded the corresponding α,β-epoxy ketones good to excellent yields in an one-pot reaction without using any transition metals or additives. Furthermore, haloketones without an α′-hydrogen are also applicable in this reaction.

  据报道，利用含有可烯醇化的α'-氢的α-卤代烷，可以有效地促进DBU的Darzens反应。该方法非对映选择性地在不使用任何过渡金属或添加剂的情况下在一锅法反应中提供了优良的优良产率的相应的α，β-环氧酮。此外，没有α'-氢的卤代酮也可用于该反应中。
• SHIBATA, IKUYA;YAMASAKI, HAYAHIDE;BABA, AKIO;MATSUDA, HARUO, SYNLETT.,(1990) N, C. 490-492
  作者：SHIBATA, IKUYA、YAMASAKI, HAYAHIDE、BABA, AKIO、MATSUDA, HARUO

  DOI：——

  日期：——