ethyl benzoylacetate-d2 | 73738-40-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl benzoylacetate-d2
• 英文别名: 2,2-dideuterio-3-oxo-3-phenyl-propionic acid ethyl ester；Ethyl 2,2-dideuterio-3-oxo-3-phenylpropanoate
• CAS: 73738-40-6
• 化学式: C₁₁H₁₂O₃
• 分子量: 194.199
• InChiKey: GKKZMYDNDDMXSE-MGVXTIMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  ethyl benzoylacetate-d2 在 四氯化碳 、 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 三苯基膦 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 87.0h， 生成 α,α-dideutero-β-chloropropiophenone
  参考文献：
  名称：

  The mode of bakers' yeast transformation of 3-chloropropiophenone and related ketones. Synthesis of (2S)-[2-2H]propiophenone, (R)-fluoxetine, and (R)- and (S)-fenfluramine

  摘要：

  Yeast treatment of 3-chloropropiophenone (2) affords the expected (1S)-3-chloro-1-phenylpropan-1-ol (3) as well as ca. 30% of propiophenone (5). The conversion of 2 into 5 is accompanied by formal elimination of hydrochloric acid, followed by yeast saturation of the double bond of the intermediate phenyl vinyl ketone (4). Monodeuteriopropiophenone formed via yeast treatment from alpha,alpha-dideuterio-3-chloropropiophenone (8) was shown to possess the 2S configuration 10 by conversion into [2-H-2]-(1R,2S)-1-phenylpropan-1-ol (13), whose stereochemistry was assigned by comparison of its NMR properties with those of the [2-H-2]-(1S,2S) diastereoisomer 19 synthesized from yeast-generated (1R,2S)-1-phenylpropane-1,2-diol (15). Whereas product 3 is converted into (R)-fluoxetine (31), 2S alcohol 24, obtained in the yeast reduction of the ketone 22 is transformed into (R)-fenfluramine (29) and into its enantiomer (26).

  DOI：

  10.1021/jo00021a011
• 作为产物：
  描述：

  苯甲酰乙酸乙酯 在 重水 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 ethyl benzoylacetate-d2
  参考文献：
  名称：

  The mode of bakers' yeast transformation of 3-chloropropiophenone and related ketones. Synthesis of (2S)-[2-2H]propiophenone, (R)-fluoxetine, and (R)- and (S)-fenfluramine

  摘要：

  Yeast treatment of 3-chloropropiophenone (2) affords the expected (1S)-3-chloro-1-phenylpropan-1-ol (3) as well as ca. 30% of propiophenone (5). The conversion of 2 into 5 is accompanied by formal elimination of hydrochloric acid, followed by yeast saturation of the double bond of the intermediate phenyl vinyl ketone (4). Monodeuteriopropiophenone formed via yeast treatment from alpha,alpha-dideuterio-3-chloropropiophenone (8) was shown to possess the 2S configuration 10 by conversion into [2-H-2]-(1R,2S)-1-phenylpropan-1-ol (13), whose stereochemistry was assigned by comparison of its NMR properties with those of the [2-H-2]-(1S,2S) diastereoisomer 19 synthesized from yeast-generated (1R,2S)-1-phenylpropane-1,2-diol (15). Whereas product 3 is converted into (R)-fluoxetine (31), 2S alcohol 24, obtained in the yeast reduction of the ketone 22 is transformed into (R)-fenfluramine (29) and into its enantiomer (26).

  DOI：

  10.1021/jo00021a011

文献信息

• Visible-light-induced α-oxyamination of 1,3-dicarbonyls with TEMPO <i>via</i> a photo(electro)catalytic process applying a DSSC anode or in a DSSC system
  作者：Ming Gong、Jung Keun Kim、Xiuli Zhao、Yabo Li、Jianye Zhang、Mengmeng Huang、Yangjie Wu

  DOI：10.1039/c9gc01154d

  日期：——

  enviromentally friendly photoelectrocatalytic one-pot method was developed for the α-oxyamination between 1,3-dicarbonyls and TEMPO via a photo(electro)catalytic process using visible light as the energy source. The recovered DSSC anode (photocatalyst) could be used more than 8 times, at the same time, the α-oxyamination reaction proceeding in the DSSC device might be involved in the photoelectrocatalysis

  开发了一种绿色环保的光电催化一锅法，以可见光为能源，通过光电催化过程在1,3-二羰基和TEMPO之间进行α-氧化。回收的DSSC阳极（光催化剂）可以使用8次以上，同时，DSSC装置中进行的α-氧胺化反应可能参与光电催化过程。机理研究表明，该反应可能同时经历可见光诱导的自由基和离子反应过程。
• Dioxane promoted photochemical O-alkylation of 1,3-dicarbonyl compounds beyond carbene insertion into C–H and C–C bonds
  作者：Xinlong Zhou、Jingjing Jiang、Min Zhang、Qingqing Wu、Keyong Zhu、Dongjie Shi、Sensen Hou、Jingjing Zhao、Pan Li

  DOI：10.1039/d4cc00778f

  日期：——

  A photochemical synthesis of enol ethers and furan-3(2H)-ones from 1,3-dicarbonyl compounds and aryl diazoacetates has been developed. Significantly, 1,4-dioxane promoted O-alkylation of various 1,3-dicarbonyl compounds beyond previous carbene insertion into C–H and C–C bonds has been disclosed.

  已经开发出由1,3-二羰基化合物和重氮乙酸芳基酯光化学合成烯醇醚和呋喃-3( 2H )-酮的方法。值得注意的是，1,4-二恶烷促进了各种1,3-二羰基化合物的O-烷基化，超越了之前卡宾插入C-H和C-C键的作用。
• Potent mechanism-based inhibition of the TEM-1 .beta.-lactamase by novel N-sulfonyloxy .beta.-lactams
  作者：Alexey Bulychev、Michael E. O'Brien、Irina Massova、Min Teng、Tracy A. Gibson、Marvin J. Miller、Shahriar Mobashery

  DOI：10.1021/ja00127a005

  日期：1995.6

  A novel class of N-sulfonyloxy beta-lactam molecules are described as potent mechanism-based inactivators for the bacterial TEM-1 beta-lactamase, a prototypic class A enzyme. These molecules inactivate the enzyme with k(inact)/K-i values in the range of 1-7 x 10(4) M(-1) s(-1) and partition ratios (i.e., k(cat)/k(inact)) of 2-7. The mechanism of action of these inactivators was investigated. These molecules acylate the active-site serine of the TEM-1 beta-lactamase, a process that results in the release of the sulfonate attached to the lactam nitrogen, giving rise to a proposed beta-amino cinnamoyl derivative as the inhibitory species. This species undergoes gradual hydrolysis with concomitant recovery of activity, the rate constants for which were evaluated.
• SCHAAL C.; RICARD M., J. LABELLED COMPOUNDS AND RADIOPHARM., 1979, 16 NO 5 727-733
  作者：SCHAAL C.、 RICARD M.

  DOI：——

  日期：——