methyl 4-benzoyloxymethylbenzoate | 24318-47-6

• 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: methyl 4-benzoyloxymethylbenzoate
• 英文别名: (4-methyloxycarbonyl)benzyl benzoate；Benzoesaeure-p-methoxycarbonyl-benzylester；Methyl 4-[(benzoyloxy)methyl]benzoate；methyl 4-(benzoyloxymethyl)benzoate
• CAS: 24318-47-6
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: AIKNWQVBSFMVRC-UHFFFAOYSA-N

物化性质

• 沸点：
  402.4±28.0 °C(predicted)
• 密度：
  1.196±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  对甲基苯甲酸甲酯 、 苯甲醛 在 叔丁基过氧化氢 、 四丁基碘化铵 作用下， 反应 17.0h， 以52%的产率得到methyl 4-benzoyloxymethylbenzoate
  参考文献：
  名称：

  Bu4NI-catalyzed benzylic acyloxylation of alkylarenes with aromatic aldehydes

  摘要：

  已经开发了一种nBu4NI催化的苄位C-H酰氧基化反应，该反应使用易得芳香醛与烷基芳烃进行，在温和且干净的反应条件下进行，采用叔丁基过氧化氢作为绿色终端氧化剂。

  DOI：

  10.1039/c2cc35450k

文献信息

• Esterification of carboxylic acids with alkyl halides using imidazolium based dicationic ionic liquids containing bis-trifluoromethane sulfonimide anions at room temperature
  作者：Arvind H. Jadhav、Kyuyoung Lee、Sangho Koo、Jeong Gil Seo

  DOI：10.1039/c5ra00802f

  日期：——

  Task-specific RTILs of symmetrical N-methylimidazolium rings linked to an oligo (ethylene glycol) chain (cationic part) and bis-trifluoromethane sulfonimide (anionic part) were synthesized, and the physicochemical properties with catalytic activity were determined.

  将对称的N-甲基咪唑环与寡聚（乙二醇）链（阳离子部分）和双三氟甲磺酰亚胺（阴离子部分）相连的特定任务离子液体（Task-specific RTILs）合成，并确定其物理化学性质和催化活性。
• Systematic Evaluation of Sulfoxides as Catalysts in Nucleophilic Substitutions of Alcohols
  作者：Sebastian Motsch、Christian Schütz、Peter H. Huy

  DOI：10.1002/ejoc.201800907

  日期：2018.9.9

  Out of an in‐depth study of a range of sulfinyl compounds in the transformation of alcohols into chloro alkanes emerged (2‐methoxyphenyl)methyl sulfoxide as optimal Lewis base catalyst. While this catalyst allowed the synthesis of benzylic chlorides in turn‐over numbers up to 50, aliphatic alcohols are non‐suitable substrates due to competing Pummerer rearrangement.

  在深入研究一系列亚砜基化合物将醇转化为氯代烷烃的过程中，出现了（2-甲氧基苯基）甲基亚砜作为最佳的路易斯碱催化剂。尽管该催化剂可以合成多达50个转换量的苄基氯，但由于竞争的Pummerer重排，脂肪族醇不适合作为底物。
• Acyl Transfer as a Problematic Side Reaction in Polymer-Supported Oligosaccharide Synthesis
  作者：Tomoo Nukada、Attila Berces、Dennis M. Whitfield

  DOI：10.1021/jo990712b

  日期：1999.12.1

  Under a wide variety of glycosylation conditions acyl transfer to the polymer support competed with glycoside formation, including the pivaloyl protecting group. As well as acyl transfer, many glycosylations also led to the formation of polymer-bound beta-1,2-linked oligomers of the donor. Using ethyl 2,6-di-O-pivaloyl-3,w4-O-isopropylidene-beta-D-galactothiopyranoside as donor under promotion of N-iodosuccinimide/silver trifluoromethanesulfonate in the presence of 2-methyl-2-butene, an 82% yield of glycoside was obtained along with pivaloylated polymer. Subsequent work showed that increasing the steric bulk about the alcoholic acceptor in conjunction with this 2-O-pivaloyl-protected glycosyl donor completely suppresses this side reaction, giving a nearly quantitative yield of glycoside. This contraintuitive approach of decreasing the reactivity of both the donor and the acceptor to minimize a side reaction is rationalized by assuming that the barrier to acyl transfer is more sensitive to the protecting groups than that of glycosylation. These developments led to a polymer-supported synthesis of the branch point trisaccharide of the group B type 1A Streptococcus capsular polysaccharide.
• Bu4NI-catalyzed benzylic acyloxylation of alkylarenes with aromatic aldehydes
  作者：Juan Huang、Lan-Tao Li、Hong-Ying Li、Ezizjan Husan、Peng Wang、Bin Wang

  DOI：10.1039/c2cc35450k

  日期：——

  An nBu4NI-catalyzed benzylic C–H acyloxylation of alkylarenes with readily available aromatic aldehydes has been developed. These reactions occur under mild and clean reaction conditions using tert-butyl hydroperoxide as the green terminal oxidant.

  已经开发了一种nBu4NI催化的苄位C-H酰氧基化反应，该反应使用易得芳香醛与烷基芳烃进行，在温和且干净的反应条件下进行，采用叔丁基过氧化氢作为绿色终端氧化剂。