Ethyl (R)-2-chloro-2-phenylethanoate | 116836-53-4

• 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: Ethyl (R)-2-chloro-2-phenylethanoate
• 英文别名: ethyl 2-chloro-2-phenylacetate；(R)-chloro-phenyl-acetic acid ethyl ester；(R)-Chlor-phenyl-essigsaeure-aethylester；ethyl (2R)-2-chloro-2-phenylacetate
• CAS: 116836-53-4
• 化学式: C₁₀H₁₁ClO₂
• mdl: MFCD00013675
• 分子量: 198.649
• InChiKey: XXRLJXZVZZXDPP-SECBINFHSA-N

物化性质

• 沸点：
  258.0±20.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (R)-chlorocarbonyloxy-phenyl-acetic acid ethyl ester 150.0 ℃ 、1.87 kPa 条件下， 生成 Ethyl (R)-2-chloro-2-phenylethanoate
  参考文献：
  名称：

  Central and peripheral glucocorticoid receptor function in abdominal obesity

  摘要：

  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.

  DOI：

  10.1007/bf03343995

文献信息

• Enantioselective α-Chlorination Reactions of in Situ Generated C1 Ammonium Enolates under Base-Free Conditions
  作者：Lotte Stockhammer、David Weinzierl、Thomas Bögl、Mario Waser

  DOI：10.1021/acs.orglett.1c02256

  日期：2021.8.6

  esters can be carried out with high levels of enantioselectivities utilizing commercially available isothiourea catalysts under base-free conditions. The reaction, which proceeds via the in situ formation of chiral C1 ammonium enolates, is best carried out under cryogenic conditions combined with a direct trapping of the activated α-chlorinated ester derivative to prevent epimerization, thus allowing

  活化芳基乙酸酯的不对称 α-氯化可以在无碱条件下使用市售的异硫脲催化剂以高水平的对映选择性进行。该反应通过原位形成手性 C1 烯醇化铵进行，最好在低温条件下进行，同时直接捕获活化的 α-氯化酯衍生物以防止差向异构化，从而实现高达 er 99 的对映选择性： 1.
• Enzymatic Hydrolysis and Selective Racemisation Reactions of α-Chloro Esters
  作者：Louise Haughton、Jonathan M. J. Williams

  DOI：10.1055/s-2001-13395

  日期：——

  The kinetic resolution of a-chloro esters was effected with good selectivity using CLEC (Cross-Linked Enzyme Crystals) enzymes. The selective racemisation of a-chloro esters in the presence of alpha -chloro acids enabled a successful dynamic kinetic resolution reaction to be performed.

  使用 CLEC（交联酶晶体）酶以良好的选择性实现α-氯酯的动力学拆分。在存在 α-氯酸的情况下，α-氯酯的选择性外消旋作用能够进行成功的动态动力学拆分反应。
• Organocatalytic Stereospecific Appel Reaction
  作者：Jan Tönjes、Lukas Kell、Thomas Werner

  DOI：10.1021/acs.orglett.3c03463

  日期：2023.12.29

  Herein we report a new method for the catalytic Appel reaction by P(III)/P(V) redox cycling at very low catalyst loadings of 1–2 mol % using low amounts of hexachloroacetone as the halogen source and phenylsilane as the terminal reductant. Twenty-six alcohols and nine epoxides containing a wide variety of functional groups were converted to the respective chlorides and dichlorides in yields of up to

  在此，我们报告了一种通过 P(III)/P(V) 氧化还原循环进行催化 Appel 反应的新方法，催化剂负载量极低（1-2 mol%），使用少量六氯丙酮作为卤素源，苯基硅烷作为末端还原剂。含有多种官能团的 26 种醇和 9 种环氧化物被转化为各自的氯化物和二氯化物，产率高达 97%，对映体特异性高达 >99%，对映体比率高达 >99:1。
• 33. Experiments on the interaction of hydroxy-compounds and phosphorus and thionyl halides in the absence and in the presence of tertiary bases. Part I. Optically active β-octanol, ethyl mandelate, and phenylmethylcarbinol
  作者：William Gerrard

  DOI：10.1039/jr9440000085

  日期：——
• LVII.—The interaction of ethyl l-mandelate and thionyl chloride in the presence of pyridine. The mechanism of the replacement of hydroxyl by chlorine by means of thionyl chloride
  作者：Joseph Kenyon、Alfred George Lipscomb、Henry Phillips

  DOI：10.1039/jr9300000415

  日期：——