4-methoxyphenyl phenyl carbonate | 17145-95-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-methoxyphenyl phenyl carbonate
• 英文别名: p-methoxyphenyl phenyl carbonate；p-Methoxyphenyl-phenylcarbonat；Carbonic acid, p-methoxyphenyl phenyl ester；(4-methoxyphenyl) phenyl carbonate
• CAS: 17145-95-8
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: CDYRJVLCQQLYLL-UHFFFAOYSA-N

物化性质

• 沸点：
  348.8±25.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2920909090

反应信息

• 作为产物：
  描述：

  在 水 作用下， 以 二氯甲烷 为溶剂， 反应 10.25h， 生成 4-methoxyphenyl phenyl carbonate
  参考文献：
  名称：

  Copeland, Christopher; Stick, Robert V., Australian Journal of Chemistry, 1984, vol. 37, # 7, p. 1483 - 1487

  摘要：

  DOI：

文献信息

• Kinetic investigation of the phenolysis of phenyl 4-nitrophenyl and phenyl 2,4-dinitrophenyl carbonates
  作者：Enrique A. Castro、Mauricio Angel、Paulina Pavez、José G. Santos

  DOI：10.1039/b103397m

  日期：2001.11.29

  The reactions of phenyl 4-nitrophenyl carbonate (PNPC) and phenyl 2,4-dinitrophenyl carbonate (PDNPC) with a homogeneous series of phenoxide anions are subjected to a kinetic investigation in water at 25.0 °C, ionic strength 0.2 mol dm−3 (KCl). Under phenoxide or total phenol excess over the substrate all these reactions obey pseudo first-order kinetics and are first order in phenoxide. The Brønsted-type plots for the nucleophilic rate constants are linear with slopes 0.61 and 0.49 for the phenolysis of PNPC and PDNPC, respectively. The magnitude of these slopes and the absence of curvature in the Brønsted plot at pKa = 7.1 for the PNPC reactions are consistent with concerted mechanisms (one step) for both reaction series. PDNPC is more reactive than PNPC toward phenoxide nucleophiles; this can be explained by the presence of a second nitro group in PDNPC, which (i) leaves its carbonyl carbon more positively charged than that of PNPC, making the former a better electrophile, and (ii) makes 2,4-dinitrophenoxide a better leaving group than 4-nitrophenoxide. The larger nucleophilic rate coefficients found in this work relative to those obtained in the concerted phenolysis of 4-nitrophenyl and 2,4-dinitrophenyl methyl carbonates is explained by a stronger electron withdrawal from PhO compared to MeO. Comparison of the concerted phenolysis of PNPC with the stepwise reactions of quinuclidines with the same substrate indicates that substitution of a quinuclidino group in a zwitterionic tetrahedral intermediate by a phenoxy group greatly destabilises the intermediate.

  苯基 4-硝基苯酯 (PNPC) 和苯基 2,4-二硝基苯酯 (PDNPC) 与一系列均相酚盐阴离子的反应在水中的动力学研究在 25.0 °C，离子强度 0.2 mol dm−3（KCl）的条件下进行。在酚盐或总酚过量的情况下，这些反应均遵循拟一级动力学，并对酚盐呈现一级反应。亲核速率常数的布仑斯惕线性图的斜率分别为 0.61 和 0.49，对应于 PNPC 和 PDNPC 的酚解反应。这些斜率的值以及在 pKa = 7.1 时 PNPC 反应在布仑斯惕图中无曲率，与这两种反应系列协同机制（一步）一致。PDNPC 相对于 PNPC 对酚盐亲核试剂具有更高的反应性；这可以由 PDNPC 中的第二个硝基解释，(i)使得羰基碳比 PNPC 具有更多正电荷，从而成为更好的亲电试剂，以及 (ii) 使得 2,4-二硝基苯氧基比 4-硝基苯氧基成为更好的离去基团。本文发现的大于协同酚解反应中的 4-硝基苯甲酸酯和 2,4-二硝基苯甲酸酯甲酯的亲核速率常数，可由PhO相比MeO更强的电子抽取效应解释。将 PNPC 的协同酚解与相同底物的奎宁环的逐步反应进行比较，表明在偶极四面体中间体中用苯氧基取代奎宁环基团会极大地破坏中间体的稳定性。
• Alkyl and Aryl 4,5-Dichloro-6-oxopyridazin-1(6H)-carboxylates: A Practical Alternative to Chloroformates for the Synthesis of Symmetric and Asymmetric Carbonates
  作者：Yong-Jin Yoon、Hyo Yoon、Hyun Moon、Gi Sung

  DOI：10.1055/s-0035-1561411

  日期：——

  Symmetric and asymmetric carbonates were synthesized by using alkyl or aryl 4,5-dichloro-6-oxopyridazin-1(6 H )-carboxylates. Five aryl 4,5-dichloro-6-oxopyridazin-1(6 H )-carboxylates were converted into the corresponding diaryl carbonates in good to excellent yields by treatment with potassium carbonate in refluxing THF. When the 4,5-dichloro-6-oxopyridazin-1(6 H )-carboxylates were treated with

  通过使用烷基或芳基 4,5-dichloro-6-oxopyridazin-1(6 H)-carboxylates 合成对称和不对称碳酸酯。通过在回流的四氢呋喃中用碳酸钾处理，五种芳基 4,5-二氯-6-氧代哒嗪-1(6 H)-羧酸酯以良好到极好的产率转化为相应的碳酸二芳基酯。当 4,5-二氯-6-氧代哒嗪-1(6 H )-羧酸酯在叔丁醇钾的存在下在甲苯中在室温下用脂肪族或芳香族醇处理时，它们得到相应的对称或不对称碳酸酯。以优异的产量。因此，烷基和芳基 4,5-二氯-6-氧代哒嗪-1(6 H )-羧酸酯是氯甲酸酯的高效、稳定且环保的替代品。
• Mechanism of ipso aromatic substitution by reaction of aryloxy(methoxy)carbenes and diaryloxycarbenes with DMAD
  作者：Xiaosong Lu、John Warkentin

  DOI：10.1139/v01-029

  日期：2001.4.1

  Some aryloxy(methoxy)carbenes and diaryloxycarbenes attack dimethyl acetylenedicarboxylate (DMAD) with aryl group transfer to an alkyne carbon of DMAD. In this study diaryloxycarbenes with different aryl groups that could be transferred competitively, were generated in the presence of DMAD to probe for the mechanism of that ipso aromatic substitution. It was found that a para electron-withdrawing substituent, relative to an electron-donating substituent, facilitated migration of an aryl group. Mechanisms in accord with these findings involve initial nucleophilic attack by the carbene at an alkyne carbon of DMAD. That step is followed by either nucleophilic, ipso attack on the aromatic ring or by electron transfer, from the side chain of the aromatic ring into the ring itself.Key words: aromatic substitution, diaryloxycarbene, DMAD, ipso, nucleophilic.

  一些芳氧基（甲氧基）卡宾和二芳氧基卡宾会攻击二甲基乙炔二羧酸酯（DMAD），将芳基转移到DMAD的炔烃碳上。在这项研究中，生成了具有不同芳基的二芳氧基卡宾，这些芳基可以竞争性地转移，在DMAD存在的情况下探究那种偶极芳基取代的机制。发现对于电子给予取代基而言，相对于电子吸引取代基，对芳基的迁移起到促进作用。与这些发现一致的机制涉及卡宾在DMAD的炔烃碳上的最初亲核攻击。该步骤之后要么是对芳环的亲核偶极攻击，要么是从芳环的侧链向环本身的电子转移。关键词：芳基取代，二芳氧基卡宾，DMAD，偶极，亲核。
• Synthesis of Organic Carbonates with Alkyl/aryl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylates and ROH/AlCl₃under Ambient Condition
  作者：Gi Hyeon Sung、Bo Ram Kim、Ki Eun Ryu、Jeum-Jong Kim、Yong-Jin Yoon

  DOI：10.5012/bkcs.2014.35.9.2758

  日期：2014.9.20

  demonstrated the synthesis of organic carbonates using alkyl/aryl 4,5-dichloro-6-oxopyridazine-1(6H)carboxylates and alcohol in the presence of aluminum chloride. Alkyl/aryl 4,5-dichloro-6-oxopyridazine1(6H)-carboxylates were reacted with alcohol in the presence of AlCl3 in toluene at room temperature to afford the corresponding unsymmetric and symmetric organic carbonates in good to excellent yields. These

  我们展示了在氯化铝存在下使用烷基/芳基 4,5-二氯-6-氧代哒嗪-1(6H) 羧酸盐和醇合成有机碳酸酯。烷基/芳基 4,5-二氯-6-氧代哒嗪1(6H)-羧酸盐与醇在 AlCl3 存在下于甲苯中在室温下反应，以良好至优异的收率得到相应的不对称和对称有机碳酸酯。这些都是高效和方便的过程。烷基/芳基 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylates 是固体、稳定和无毒的 CO2/CO2R(Ar) 源。值得注意的是，该反应是在环境和酸性条件下进行的，起始原料易于制备和易得，可定量分离出可重复使用的4,5-二氯哒嗪-3(2H)-one。
• TWO-STEP AND ONE-POT PROCESSES FOR PREPARATION OF ALIPHATIC DIISOCYANATES
  申请人：Great Eastern Resins Industrial Co., Ltd.

  公开号：US20170015621A1

  公开（公告）日：2017-01-19

  The present invention relates to using a two-step (thermolysis) or one-pot process to prepare aliphatic diisocyanates from aliphatic diamines and diaryl carbonates. Polyisocyanates can also be prepared from polyamines and diaryl carbonates. The present synthetic processes do not apply phosgene or highly toxic reagents and chloro-solvents during the entire procedure.

  本发明涉及使用两步（热解）或一锅法过程从脂肪族二胺和二苯基碳酸酯制备脂肪族二异氰酸酯。也可以从多胺和二苯基碳酸酯制备多异氰酸酯。本合成过程在整个过程中不使用光气或高毒性试剂和氯溶剂。