prop-2-yn-1-yl 2-bromobenzoate | 108521-37-5

• 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: prop-2-yn-1-yl 2-bromobenzoate
• 英文别名: 2-bromo-benzoic acid, 2-propynyl ester；2-Bromobenzoic acid, propargyl ester；prop-2-ynyl 2-bromobenzoate
• CAS: 108521-37-5
• 化学式: C₁₀H₇BrO₂
• 分子量: 239.068
• InChiKey: TUQFVKRULQSDLD-UHFFFAOYSA-N

物化性质

• 沸点：
  312.6±22.0 °C(Predicted)
• 密度：
  1.491±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  prop-2-yn-1-yl 2-bromobenzoate 在 toluene dioxygenase from E_. coli JM₁₀₉ (pDTG₆₀₁A) 作用下， 反应 3.0h， 生成 propargyl (5S,6R)-5,6-dihydroxy-2-bromocyclohexa-1,3-dienecarboxylate
  参考文献：
  名称：

  Processing of o-Halobenzoates by Toluene Dioxygenase. The Role of the Alkoxy Functionality in the Regioselectivity of the Enzymatic Dihydroxylation Reaction

  摘要：

  In order to investigate the relationship between the size of a substituent on the aromatic substrate and its directing effect on the dihydroxylation, a series of 2-halobenzoates was synthesized and subjected to metabolism by toluene dioxygenase in preparative-scale fermentation cultures of Escherichia coli JM109 (pDTG601A). Larger ester substituents were shown to have a greater directing effect on the dihydroxylation reaction. Furthermore, significant increases in regioselectivity were observed using propargyl substituents, relative to the use of any other ester substituent. The selectivity and the product ratios are reported for o-fluoro-, o-chloro-, o-bromo-, and o-iodobenzoate esters (methyl, ethyl, n-propyl, allyl, and propargyl). Experimental and spectral data, as well as absolute stereochemistry, are provided for all new compounds.

  DOI：

  10.1021/op400343c
• 作为产物：
  描述：

  2-丙炔-1-醇 、 2-溴苯甲酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 0.5h， 以86%的产率得到prop-2-yn-1-yl 2-bromobenzoate
  参考文献：
  名称：

  邻羰基辅助的丙炔基羧酸盐的氧乙酰氧基化在无金属条件下保持手性

  摘要：

  提出了保留手性的伯，仲和叔炔丙基羧酸的无金属氧乙酰氧基化方法。该反应通过烷基炔酮中间体上相邻羰基的分子内亲核攻击而进行。该方法是一般的，具有广泛的底物范围，并且适用于包括从天然产物获得的那些炔丙基羧酸酯。通过同位素标记（使用H 2 O 18和D 2 O）洞察机械途径，并确认了对照实验。

  DOI：

  10.1002/adsc.201900314

文献信息

• 2-Phenyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethanol as an Efficient and Versatile Auxiliary Ligand in Copper(II)-Catalyzed Buchwald–Hartwig and Sharpless–Meldal C–N Bond-Forming Reactions
  作者：Hashem Sharghi、Pezhman Shiri

  DOI：10.1055/s-0034-1379951

  日期：——

  A highly active, air-stable, and versatile procedure for Buchwald-Hartwig and Sharpless-Meldal C-N bond formation is reported. Under nearly solvent-free conditions using copper(II) acetate and 2-phenyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethanol, a variety of N-heterocycles and various cyclic and noncyclic secondary amines were arylated to form N-aryl compounds in moderate to excellent yields. This methodology also provides rapid access to diverse 1,4-disubstituted 1,2,3-triazoles in good to excellent yields. All reactions are performed in short times under air.
• Investigation of the antimicrobial activity of a series of novel derivatives of 1,2,3-triazoles
  作者：Kh. Yuldasheva、A. D. Dzhuraev、A. G. Makhsumov、N. Amanov

  DOI：10.1007/bf00773202

  日期：1992.1
• Synthesis and antimicrobial activity of 3,3′-bis-(propyn-1,1′-benzoato)dimethylsilanes
  作者：Kh. Yuldasheva、A. D. Dzhuraev、A. G. Makhsumov、N. Amanov

  DOI：10.1007/bf00772941

  日期：1992.3
• Neighboring Carbonyl Group Assisted Oxyacetoxylation of Propargylic Carboxylates with Retention of Chirality under Metal Free Condition
  作者：Tapas R. Pradhan、Debendra K. Mohapatra

  DOI：10.1002/adsc.201900314

  日期：2019.8.5

  reaction proceeds through the intramolecular nucleophilic attack of the neighboring carbonyl group on an alkynyliodonium intermediate. The process is general with broad substrate scope and is amenable for application to a variety of propargyl carboxylates including those obtained from natural products. Insight into the mechanistic pathway by isotopic labelling (using H2O18 and D2O) and controlled experiments

  提出了保留手性的伯，仲和叔炔丙基羧酸的无金属氧乙酰氧基化方法。该反应通过烷基炔酮中间体上相邻羰基的分子内亲核攻击而进行。该方法是一般的，具有广泛的底物范围，并且适用于包括从天然产物获得的那些炔丙基羧酸酯。通过同位素标记（使用H 2 O 18和D 2 O）洞察机械途径，并确认了对照实验。
• Processing of <i>o</i>-Halobenzoates by Toluene Dioxygenase. The Role of the Alkoxy Functionality in the Regioselectivity of the Enzymatic Dihydroxylation Reaction
  作者：Jordan Froese、Mary Ann A. Endoma-Arias、Tomas Hudlicky

  DOI：10.1021/op400343c

  日期：2014.6.20

  In order to investigate the relationship between the size of a substituent on the aromatic substrate and its directing effect on the dihydroxylation, a series of 2-halobenzoates was synthesized and subjected to metabolism by toluene dioxygenase in preparative-scale fermentation cultures of Escherichia coli JM109 (pDTG601A). Larger ester substituents were shown to have a greater directing effect on the dihydroxylation reaction. Furthermore, significant increases in regioselectivity were observed using propargyl substituents, relative to the use of any other ester substituent. The selectivity and the product ratios are reported for o-fluoro-, o-chloro-, o-bromo-, and o-iodobenzoate esters (methyl, ethyl, n-propyl, allyl, and propargyl). Experimental and spectral data, as well as absolute stereochemistry, are provided for all new compounds.