(3-phenyloxiran-2-yl)(thiophen-2-yl)methanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-phenyloxiran-2-yl)(thiophen-2-yl)methanone
• 英文别名: 2-Phenyl-3-(thiophene-2-carbonyl)oxirane；(3-phenyloxiran-2-yl)-thiophen-2-ylmethanone
• 化学式: C₁₃H₁₀O₂S
• mdl: MFCD01788229
• 分子量: 230.287
• InChiKey: MHMVFBXEHDEXIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  57.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3-phenyloxiran-2-yl)(thiophen-2-yl)methanone 在 sodium dithionite 、 sodium carbonate 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 6.0h， 以86%的产率得到1-(2-thienyl)-3-hydroxy-3-phenylpropan-1-one
  参考文献：
  名称：

  磁性纳米Fe 3 O 4负载的1-苄基-1,4-二氢烟碱酰胺（BNAH）：合成及其在α，β-环氧酮的催化还原中的应用

  摘要：

  以二氧化硅包覆的磁性纳米粒子为载体，成功构建了新型的磁性可回收有机氢化物。制备的磁性有机氢化物化合物BNAH（1-苄基-1,4-二氢烟酰胺）在催化还原α，β-环氧酮中显示出有效的活性。反应后，可以通过简单的磁性分离来分离磁性纳米粒子负载的BNAH，这使得产物的分离更容易。

  DOI：

  10.1021/ol203423u
• 作为产物：
  描述：

  3-phenyl-1-thiophen-2-yl-propenone 在 双氧水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (3-phenyloxiran-2-yl)(thiophen-2-yl)methanone
  参考文献：
  名称：

  Biomimetic hydrogenation: a reusable NADH co-enzyme model for hydrogenation of α,β-epoxy ketones and 1,2-diketones

  摘要：

  A biomimetic method has been developed to transform alpha,beta-epoxy ketones or 1,2-diketones into corresponding beta-hydroxy ketones or alpha-hydroxy ketones using a catalytic amount of BNAH or BNA(+)Br(-). The regeneration of BNAH or BNA(+)Br(-) is achieved by a mixture of HCOOH/Et3N. A radical mechanism is proposed to explain these observations. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.047

文献信息

• Kinetic resolution of 2,3-epoxy 3-aryl ketones via catalytic asymmetric ring-opening with pyrazole derivatives
  作者：Tianyu Huang、Lili Lin、Xiaolei Hu、Jianfeng Zheng、Xiaohua Liu、Xiaoming Feng

  DOI：10.1039/c5cc02179k

  日期：——

  A highly efficient catalytic kinetic resolution of 2,3-epoxy 3-aryl ketones via asymmetric ring-opening with pyrazole derivatives has been achieved by using a chiral N,N′-dioxide–Sc(iii) complex as the catalyst.

  一种高效的催化动力学拆分2,3-环氧基3-芳基酮，通过使用手性N,N′-二氧化物-Sc(iii)复合物作为催化剂，通过与吡唑衍生物的不对称环开启实现。
• PAA-supported Hantzsch 1,4-dihydropyridine ester: an efficient catalyst for the hydrogenation of α,β-epoxy ketones
  作者：Xin-Feng Zhou、Peng-Fei Wang、Ye Geng、Hua-Jian Xu

  DOI：10.1016/j.tetlet.2013.07.112

  日期：2013.9

  A new type of water-soluble polymer-supported NADH co-enzyme model-FAA (polyacrylic acid)-supported Hantzsch 1,4-dihydropyridine ester (PM-HEH) was designed and synthesized. Catalytic amount of the supported reagent was used in the hydrogenation of alpha,beta-epoxy ketones to the corresponding beta-hydroxy ketones and showed great catalytic efficiency in the reduction reaction. This PAA-HEH was an optimal potential for recycling use. (C) 2013 Elsevier Ltd. All rights reserved.
• Catalytic Hydrogenation of α,β-Epoxy Ketones to Form β-Hydroxy Ketones Mediated by an NADH Coenzyme Model
  作者：Hua-Jian Xu、You-Cheng Liu、Yao Fu、Yun-Dong Wu

  DOI：10.1021/ol0610892

  日期：2006.8.1

  The hydrogenation of alpha,beta-epoxy ketones can be mediated by a catalytic amount of BNAH or BNA(+) Br- to form corresponding,beta-hydroxy ketones in high yield. Na2S2O4 is used as the reducing agent to convert BNA(+) Br- to BNAH. A radical mechanism has been proposed to understand many observations of this catalytic reaction.
• GHONEIM, K. M.;BADRAN, M. M.;SHAABAN, M. A.;EL-MELIGIE, S., EGYPT. J. PHARM. SCI., 29,(1988) N-4, C. 563-570
  作者：GHONEIM, K. M.、BADRAN, M. M.、SHAABAN, M. A.、EL-MELIGIE, S.

  DOI：——

  日期：——