3-(Trifluoromethyl)benzyl acetate

• 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: 3-(Trifluoromethyl)benzyl acetate
• 英文别名: 3-(Trifluoromethyl) benzyl alcohol, acetate；[3-(trifluoromethyl)phenyl]methyl acetate
• 化学式: C₁₀H₉F₃O₂
• 分子量: 218.175
• InChiKey: WXMPHCXJKNKNBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  3
• 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：
  5

反应信息

• 作为反应物：
  描述：

  3-(Trifluoromethyl)benzyl acetate 生成 1-乙基-3-(三氟甲基)苯
  参考文献：
  名称：

  Pincock J.A., Wedge P.J., J. Org. Chem., 59 (1994) N 19, 5587-5595

  摘要：

  DOI：
• 作为产物：
  描述：

  3-三氟甲基苯甲醇 、 乙酰氯 在 吡啶 作用下， 以 苯 为溶剂， 生成 3-(Trifluoromethyl)benzyl acetate
  参考文献：
  名称：

  The Photochemistry of Methoxy-Substituted Benzyl Acetates and Benzyl Pivalates: Homolytic vs Heterolytic Cleavage

  摘要：

  The multiple methoxy-substituted benzyl acetates (3g-i) and benzyl pivalates (4g-i) have been photolyzed in methanol solution. The products of these reactions are derived from two critical intermediates; the benzyl radical/acyloxy radical pair and the benzyl cation/carboxylate anion pair. As predicted by the meta effect, the yield of ion-derived product, the methyl ether in this case, was enhanced by the presence of the m-methoxy groups. The yield of ether, for the acetate esters, varied from 2% for the 4-methoxy-substituted ester to 66% for the 3,4,5-trimethoxy-substituted ester. In contrast, the yield of ether, for the pivalate esters, varied from <1% for the 4-methoxy-substituted ester to 20% for the 3,4,5-trimethoxy-substituted one. The meta effect does not explain these differences; electron transfer converting the radical pair to the ion pair is still an important pathway in the mechanism for ion formation. A quantitative analysis of the yield of the ethers was done in order to obtain the electron-transfer rate constants. This analysis revealed that the yield of the ethers was higher than expected based on previous results for other substituted benzyl acetates. A possible explanation for this discrepancy is that internal return of the radical pair to starting material for the acetate esters is more efficient than for the pivalate esters. Also, the esters 3k and 3l, were prepared to study the effect of electron-withdrawing groups in the meta position. For these esters, the benzylic cleavage reactions were inefficient and an isomerization reaction, the benzvalene rearrangement, was competitive.

  DOI：

  10.1021/jo00098a016

文献信息

• Cyanothiophene derivatives, compositions containing such compounds and methods of use
  申请人：——

  公开号：US20040097557A1

  公开（公告）日：2004-05-20

  The present invention addresses substituted cyanothiophene derivatives of the formula I: 1 as well as compositions containing such compounds and methods of treatment. The compounds in the present invention are glucagon antagonists. The compounds block the action of glucagon at its receptor and thereby decrease the levels of plasma glucose providing a treatment of diabetes.

  本发明涉及式I的取代氰基噻吩衍生物，如1所示，以及含有这种化合物的组合物和治疗方法。本发明中的化合物是胰高血糖素拮抗剂。这些化合物阻断了胰高血糖素在其受体上的作用，从而降低血浆葡萄糖水平，提供糖尿病的治疗。
• Boryl Radical-Promoted Deoxygenative Alkylation of Benzyl Acetates
  作者：Feng-Lian Zhang、Yi-Feng Wang、Nan-Nan Liu、Xuan-Chen Wan、Li-Wen Hui

  DOI：10.1055/s-0042-1751463

  日期：2024.6

  Deoxygenative alkylation of benzyl alcohols was realized by using acetate as the alcohol activation group. The C–O bond homolysis is achieved by a boryl radical-promoted β-scission process. The strategy is amenable to a variety of benzyl alcohols, including primary, secondary, and more challenging tertiary alcohols. The synthetic practicability was demonstrated by a gram-scale one-pot reaction.

  以乙酸酯为醇活化基团，实现了苯甲醇的脱氧烷基化。C-O键均裂是通过硼基自由基促进的β-断裂过程实现的。该策略适用于各种苯甲醇，包括伯醇、仲醇和更具挑战性的叔醇。通过克级一锅反应证明了合成的实用性。
• Photoredox-Neutral Deoxygenative Carboxylation of Acylated Alcohols with Tetrabutylammonium Oxalate
  作者：Chen-Wei Xu、Si-Yi Yan、Hui Xu、Sai Wang、Li-Qun Gu、Pei Xu、Long Yin、Xu Zhu

  DOI：10.1021/acscatal.4c03396

  日期：2024.8.16

  Herein, a photoredox-neutral strategy for carboxylation of acylated alcohols via C(sp3)–O bond activation and cleavage with tetrabutylammonium oxalate (TBAO) as the carbonyl source and reductant as well as the promoter is described. Neither a pre-established CO2 atmosphere nor external electron donors are required as the TBAO is crucial for the transformation. Various primary, secondary, and tertiary

  本文描述了一种光氧化还原中性策略，以草酸四丁基铵 (TBAO) 作为羰基源和还原剂以及促进剂，通过 C(sp 3 )-O 键活化和裂解来羧化酰化醇。既不需要预先建立的CO 2气氛，也不需要外部电子供体，因为TBAO对于转变至关重要。各种伯醇、仲醇和叔醇可以顺利转化为相应的芳基乙酸，这是多种药物的核心结构。
• BACIOCCHI, ENRICO;GIACCO, TIZIANA DEL;ROL, CESARE;SEBASTIANI, GIOVANNI VI+, TETRAHEDRON LETT., 30,(1989) N7, C. 3573-3576
  作者：BACIOCCHI, ENRICO、GIACCO, TIZIANA DEL、ROL, CESARE、SEBASTIANI, GIOVANNI VI+

  DOI：——

  日期：——
• DIPEPTIDYL PEPTIDASE INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES
  申请人：Merck & Co., Inc.

  公开号：EP1385508B1

  公开（公告）日：2008-05-21