3-hydroxybenzenemethanol benzoate | 106262-12-8

• 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-hydroxybenzenemethanol benzoate
• 英文别名: Benzoic acid 3-hydroxybenzyl ester；(3-hydroxyphenyl)methyl benzoate
• CAS: 106262-12-8
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: RNXDSUVYRWSRJD-UHFFFAOYSA-N

物化性质

• 熔点：
  72-72.5 °C
• 沸点：
  388.5±17.0 °C(Predicted)
• 密度：
  1.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxybenzenemethanol benzoate 、 9-chloromethyl-10-decylanthracene 在 18-冠醚-6 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以97%的产率得到3-[(10-decylanthracen-9-yl)methoxy]benzyl benzoate
  参考文献：
  名称：

  Synthesis and characterization of anthracene-clustering dendrimers: observation of fluorescence resonance energy transfer in the multichromophoric system

  摘要：

  A series of anthracene-clustering dendrimers bearing various aliphatic substituents at the terminal positions were synthesized using a direct coupling strategy. A remarkable effect of the side chains was imparted to chemical properties of the dendrimers such as drastically increased solubility. Although the multibranched anthracene arrays in the dendritic architectures exhibited no cooperativity in terms of the absorption feature and behaved as single chromophoric systems, investigations focusing on fluorescence properties revealed that a type of cooperativity was present as expressed in the reduced quantum yields of fluorescence. An alternative approach utilizing time-resolved fluorescence decay measurements clearly demonstrated that the most reasonable mechanism of the cooperative action should involve two discernible channels of intramolecular fluorescence resonance energy transfer (FRET) occurring from one chromophore to the others within and across junctions of the branching units. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.096
• 作为产物：
  描述：

  3-hydroxybenzenemethanol dibenzoate 在 正丁胺 作用下， 以 苯 为溶剂， 反应 3.5h， 以91%的产率得到3-hydroxybenzenemethanol benzoate
  参考文献：
  名称：

  Bell, Kevin H., Australian Journal of Chemistry, 1987, vol. 40, # 10, p. 1723 - 1735

  摘要：

  DOI：

文献信息

• A microwave-assisted highly practical chemoselective esterification and amidation of carboxylic acids
  作者：Gunindra Pathak、Diparjun Das、Samuel Lalthazuala Rokhum

  DOI：10.1039/c6ra22558f

  日期：——

  The ubiquitousness of esters and amide functionalities makes their coupling reaction one of the most sought-after organic transformations. Herein, we have described an efficient microwave-assisted synthesis of esters and amides. Soluble triphenylphosphine, in conjugation with molecular iodine, gave the desired products without the requirement for a base/catalyst. In addition, a solid-phase synthetic

  酯和酰胺官能团无处不在，使它们的偶联反应成为最受欢迎的有机转化之一。在此，我们已经描述了酯和酰胺的有效微波辅助合成。可溶性三苯基膦与分子碘结合，可得到所需的产物，而无需碱/催化剂。另外，为所述转化引入了固相合成路线，其与溶液相路线相比具有更多的优点，例如低湿度敏感性，易于处理，通过简单过滤分离产物和可重复使用性。简而言之，我们的方法本质上是简单，温和，绿色和高度化学选择性的。
• Organocatalytic selective benzoylation of alcohols with trichloromethyl phenyl ketone: inverse selectivity in benzoylation of alcohols containing phenol or aromatic amine functionality
  作者：Ram N. Ram、Vineet Kumar Soni、Dharmendra Kumar Gupta

  DOI：10.1016/j.tet.2012.08.051

  日期：2012.11

  organocatalyst at room temperature in high yields and excellent selectivity. It also shows the potential to selectively benzoylate primary alcoholic groups of aminoarylalkanols and primary-secondary diols as well as primary amino group of alkyl amines in the presence of aryl amines under similar conditions. A rationale for the selectivity and efficiency of the reaction has been provided.

  在室温下，当2-10 mol％的PMDETA有机催化剂存在时，三氯甲基苯基酮苯甲酸酯化还含有酚基的化合物中的伯和仲脂肪醇基团，具有很高的收率和优异的选择性。它也显示了在类似条件下在芳基胺存在下选择性地苯甲酰化氨基芳基链烷醇和伯-仲二醇的伯醇基以及烷基胺的伯氨基的潜力。已经提供了反应的选择性和效率的原理。
• Understanding in Vivo Benzenoid Metabolism in Petunia Petal Tissue
  作者：Jennifer Boatright、Florence Negre、Xinlu Chen、Christine M. Kish、Barbara Wood、Greg Peel、Irina Orlova、David Gang、David Rhodes、Natalia Dudareva

  DOI：10.1104/pp.104.045468

  日期：2004.8.1

  In vivo stable isotope labeling and computer-assisted metabolic flux analysis were used to investigate the metabolic pathways in petunia (Petunia hybrida) cv Mitchell leading from Phe to benzenoid compounds, a process that requires the shortening of the side chain by a C2 unit. Deuterium-labeled Phe (2H5-Phe) was supplied to excised petunia petals. The intracellular pools of benzenoid/phenylpropanoid-related compounds (intermediates and end products) as well as volatile end products within the floral bouquet were analyzed for pool sizes and labeling kinetics by gas chromatography-mass spectrometry and liquid chromatography-mass spectrometry. Modeling of the benzenoid network revealed that both the CoA-dependent, β-oxidative and CoA-independent, non-β-oxidative pathways contribute to the formation of benzenoid compounds in petunia flowers. The flux through the CoA-independent, non-β-oxidative pathway with benzaldehyde as a key intermediate was estimated to be about 2 times higher than the flux through the CoA-dependent, β-oxidative pathway. Modeling of 2H5-Phe labeling data predicted that in addition to benzaldehyde, benzylbenzoate is an intermediate between l-Phe and benzoic acid. Benzylbenzoate is the result of benzoylation of benzyl alcohol, for which activity was detected in petunia petals. A cDNA encoding a benzoyl-CoA:benzyl alcohol/phenylethanol benzoyltransferase was isolated from petunia cv Mitchell using a functional genomic approach. Biochemical characterization of a purified recombinant benzoyl-CoA:benzyl alcohol/phenylethanol benzoyltransferase protein showed that it can produce benzylbenzoate and phenylethyl benzoate, both present in petunia corollas, with similar catalytic efficiencies.

  采用体内稳定同位素标记和计算机辅助代谢通量分析，研究了从苯丙氨酸到苯环化合物的代谢途径，这个过程需要将侧链缩短一个C2单元的方式。氘标记的苯丙氨酸（2H5-Phe）被提供给切除的矮牵牛（Petunia hybrida）Mitchell品种的花瓣。通过气相色谱-质谱和液相色谱-质谱分析花香中的苯环/苯丙素相关化合物（中间产物和终产物）以及挥发性终产物的细胞内库大小和标记动力学。苯环网络的建模表明，CoA依赖性β氧化和CoA非依赖性非β氧化途径都对矮牵牛花中苯环化合物的形成做出了贡献。以苯甲醛为关键中间体的CoA非依赖性非β氧化途径通量估计约为CoA依赖性β氧化途径通量的2倍。2H5-Phe标记数据的建模预测，除了苯甲醛外，苄基苯甲酸酯是L-苯丙氨酸和苯甲酸之间的中间体。苄基苯甲酸酯是苄基醇苯甲酰化的产物，在矮牵牛花瓣中检测到了其活性。利用功能基因组学方法，从矮牵牛Mitchell品种中分离了编码苯丙醇/苄醇苯甲酰转移酶的苯乙酰-CoA：苄醇/苯乙醇苯甲酰转移酶的cDNA。对纯化重组苯乙酰-CoA：苄醇/苯乙醇苯甲酰转移酶蛋白的生化特性进行了表征，表明它可以产生苄基苯甲酸酯和苯乙基苯甲酸酯，两者在矮牵牛花冠中具有类似的催化效率。

• Facile selective aminolysis of phenolic benzoates with 1-butanamine in benzene
  作者：Kevin H. Bell

  DOI：10.1016/s0040-4039(00)84503-7

  日期：——
• BELL K. H., TETRAHEDRON LETT., 27,(1986) N 20, 2263-2264
  作者：BELL K. H.

  DOI：——

  日期：——