benzoic acid (R)-(ethoxycarbonyl)(phenyl)methyl ester | 210548-89-3

• 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: benzoic acid (R)-(ethoxycarbonyl)(phenyl)methyl ester
• 英文别名: (R)-benzoyloxy-phenyl-acetic acid ethyl ester；(R)-Benzoyloxy-phenyl-essigsaeure-aethylester；[(1R)-2-ethoxy-2-oxo-1-phenylethyl] benzoate
• CAS: 210548-89-3
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: BRHKCCHBDGKOPK-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-benzoyl-4-benzylidene-1,4-dihydro-pyridine 以 乙醚 、 二氯甲烷 为溶剂， 反应 16.33h， 生成 benzoic acid (R)-(ethoxycarbonyl)(phenyl)methyl ester
  参考文献：
  名称：

  N-Acylpyridinium Trifluoromethanesulfonates and Tetrafluoroborates: Shuttle Reagents for the Acylation of Enantiopure Secondary Alcohols

  摘要：

  DOI：

  10.1055/s-1998-2074

文献信息

• Asymmetric Catalytic Insertion of α-Diazo Carbonyl Compounds into O–H Bonds of Carboxylic Acids
  作者：Fei Tan、Xiaohua Liu、Xiaoyu Hao、Yu Tang、Lili Lin、Xiaoming Feng

  DOI：10.1021/acscatal.6b02184

  日期：2016.10.7

  An efficient enantioselective insertion of α-diazoesters and α-diazoketones into O–H bonds of carboxylic acids was realized by the use of Rh2(OAc)4 and a chiral guanidine. Optically active α-acyloxy carbonyl compounds were generated under mild reaction conditions in high yields (up to 99%) and good enantioselectivities (up to 97.5:2.5 er).

  通过使用Rh 2（OAc）4和手性胍，可以有效地将α-二重氮酸酯和α-二重氮酮插入羧酸的O-H键中。在温和的反应条件下以高收率（最高99％）和良好的对映选择性（最高97.5：2.5 er）生成旋光性α-酰氧基羰基化合物。
• Cu(II)−Aza(bisoxazoline)-Catalyzed Asymmetric Benzoylations
  作者：Anja Gissibl、M. G. Finn、Oliver Reiser

  DOI：10.1021/ol0505252

  日期：2005.6.1

  Racemic 1,2-diols and a-hydroxy carbonyl compounds can be asymmetrically benzoylated in a kinetic resolution in the presence of various Cu(II)-aza(bisoxazoline) catalysts. A novel bisbenzyl-substituted aza(bisoxazoline) ligand proved to be especially effective when immobilized on MeOPEG(5000), giving from 91 to >= 99% ee in 37-49% yield for each of five sequential reactions.
• Central and peripheral glucocorticoid receptor function in abdominal obesity
  作者：T. Ljung、M. Ottosson、A. C. Ahlberg、S. Edén、B. Odén、S. Okret、M. Brönnegård、P. Stierna、P. Björntorp

  DOI：10.1007/bf03343995

  日期：2002.3

  Abdominal obesity seems to be associated with a moderately deranged feedback regulation of the hypothalamic-pituitary-ad renal (HPA) axis where central glucocorticoid receptors (GR) are involved. Therefore, functions of central and peripheral GR were compared in this study. Furthermore, since trinucleotide repeats in early exons of steroid hormone receptor genes influence transcription, and therefore may influence receptor density, this was also studied. Ten middle-aged men, 5 with abdominal obesity and 5 controls, were studied. The suppression of dexamethasone (dex) on serum cortisol was used in dose-response tests to assess the function of central GR. Abdominal adipose tissue biopsies were incubated and exposed to cortisol in different concentrations, and the function of the peripheral GR assayed as induction of lipoprotein lipase (LPL) activity. Aberrant expansion of exonic trinucleotide repeats in the first coding exon of the GR gene was studied by sequencing of genomic DNA. Results showed that men with abdominal obesity showed less inhibition of serum cortisol by dex, particularly at lower concentrations, while in the controls cortisol secretion was inhibited in an apparent dose-response manner. LPL activity in adipose tissue was lower in abdominal obese men than in controls. However, the sensitivity to cortisol was not different between the groups. There was no evidence for expansion of trinucleotide repeats. These results suggest that the central GR and the peripheral GR in adipose tissue exhibit functional differences in abdominal obesity.