双(4-氰基苯基)碳酸酯 | 86031-12-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 双(4-氰基苯基)碳酸酯
• 英文名称: bis(4-cyanophenyl) carbonate
• 英文别名: bis(4-cyanophenyl)carbonate
• CAS: 86031-12-1
• 化学式: C₁₅H₈N₂O₃
• 分子量: 264.24
• InChiKey: POSZYPCJRYUXEU-UHFFFAOYSA-N

物化性质

• 熔点：
  107-120 °C
• 沸点：
  450.5±30.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  双(4-氰基苯基)碳酸酯 在 一水合肼 、 sodium sulfate 、 三氟乙酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 76.0h， 生成 p-tolyl p-cyanophenyl phenyl orthoformate
  参考文献：
  名称：

  Diarylo×ycarbenes from o×adiazolines

  摘要：

  Symmetric and unsymmetric 2,2-diaryloxy-5,5-dimethyl-Delta (3)-1,3,4-oxadiazolines were synthesized by oxidative cyclization of aryloxycarbonyl hydrazones of acetone with lead tetraacetate and subsequent treatment of the product mixture with a phenol in acidic solution. Thermolysis of the oxadiazolines in benzene solution at 110 degreesC afforded carbonyl ylide intermediates that cyclize, in part, to the corresponding 2,2-diaryloxyoxirane intermediates. The oxiranes, which were not observed, are required to account for the 1,1-diaryloxy-2-methylpropenes (ketene acetals) that were isolated. Most of the carbonyl ylides fragment to acetone and diaryloxycarbenes. The latter form dimers (tetraaryloxyethenes) or they can be trapped with phenols to form orthoformates. Diphenoxycarbene was also trapped with dimethyl acetylenedicarboxylate (DMAD). The method appears to be the first for generating the parent diphenoxycarbene under relatively mild conditions in solution, and the only one to date for generating unsymmetrically substituted diaryloxycarbenes. Minor competing fragmentations of the oxadiazolines to 2-diazopropane and the appropriate diaryl carbonates, were also observed.

  DOI：

  10.1139/cjc-79-3-319
• 作为产物：
  描述：

  氯仿 、 4-羟基苯甲腈 在 吡啶 、 氧气 作用下， 反应 1.0h， 以62%的产率得到双(4-氰基苯基)碳酸酯
  参考文献：
  名称：

  与氯仿的按需光碱催化光气化反应：芳基碳酸酯和卤代碳酸酯的合成

  摘要：

  碳酸酯在有机合成中用作 C1 结构单元的溶剂和试剂。该研究报告了一种新型的光按需原位合成碳酸酯与 CHCl 3溶液，其中CHCl 3溶液包含具有相对较高酸度的芳香族或卤代烷基醇和有机碱的混合物。我们发现，CHCl 3溶液中醇和碱的酸碱相互作用在光化学反应中起着关键作用。该反应允许实际合成碳酸二苯酯衍生物、卤代烷基碳酸酯和聚碳酸酯，它们是工业中重要的化学品和材料。

  DOI：

  10.1021/acs.joc.1c01210

文献信息

• Kinetic Study of the Phenolysis of Bis(4-nitrophenyl) Carbonate, Bis(4-nitrophenyl) Thionocarbonate, and Methyl 4-Nitrophenyl Thionocarbonate
  作者：Enrique A. Castro、Mauricio Angel、David Arellano、José G. Santos

  DOI：10.1021/jo0101252

  日期：2001.10.1

  The reactions of a homogeneous series of phenols with bis(4-nitrophenyl) carbonate (BNPC), bis(4-nitrophenyl) thionocarbonate (BNPTOC), and methyl 4-nitrophenyl thionocarbonate (MNPTOC) are subjected to a kinetic investigation in water, at 25.0 degrees C and ionic strength of 0.2 M (KCl). Under excess of phenol over the substrate, all the reactions obey pseudo-first-order kinetics and are first order

  均相系列苯酚与碳酸双（4-硝基苯酯），双（4-硝基苯基）硫代碳酸酯（BNPTOC）和4-硝基苯基硫代碳酸甲酯（MNPTOC）的反应在水中进行25.0摄氏度，离子强度为0.2 M（KCl）。在底物上过量的苯酚下，所有反应均遵循拟一级反应动力学，并且在酚盐阴离子中为一级反应。BNPC的反应显示出线性的Bönsted型图，斜率β= 0.66，与一致的机理一致（一个步骤）。相比之下，BNPTOC和MNPTOC的双相布朗斯台德图在高pK（a）时斜率分别为β= 0.30和0.44，在低pK（a）时斜率分别为β= 1.25和1.60，与逐步一致机制。对于两种硫代碳酸酯的反应，布朗斯台德图中心（pK（a）（0））的pK（a）值为7.1，它对应于4-硝基苯酚的pK（a）。这证实了硫代碳酸酯的酚类是逐步过程，形成了阴离子四面体中间体。通过比较标题反应和相似反应的动力学和机理，可以得出以下结论：（i）在阴离子四
• Process for manufacturing aryl ethers having different substituents on
  申请人：Institut Francais du Petrole

  公开号：US04596680A1

  公开（公告）日：1986-06-24

  A asymmetrical aryl ether of the formula X--Ar--O--Ar'--Y, wherein Ar and Ar' are each a divalent aromatic radical, X and Y are electron attracting atoms or groups which differ from each other or have different positions on the corresponding aromatic radicals, is produced by heating together, in the presence of a basic catalyst, equimolecular amounts of two aryl carbonates of the formulas: X--Ar--O--CO--O--Ar--X, and Y--Ar'--O--CO--O--Ar'--Y

  一个不对称的芳基醚的化学式为X--Ar--O--Ar'--Y，其中Ar和Ar'各自是二价芳香基团，X和Y是吸电子原子或基团，它们彼此不同或在相应的芳香基团上有不同位置。通过在碱性催化剂存在下加热两个芳基碳酸酯的等摩尔量，即X--Ar--O--CO--O--Ar--X和Y--Ar'--O--CO--O--Ar'--Y的化学式，可以制备这种醚。
• [EN] A NEW METHOD FOR THE PREPARATION OF SOLIFENACIN AND NEW INTERMEDIATE THEREOF<br/>[FR] NOUVEAU PROCÉDÉ DE PRÉPARATION DE LA SOLIFÉNACINE ET NOUVEL INTERMÉDIAIRE DANS SA PRÉPARATION
  申请人：MEGAFINE PHARMA P LTD

  公开号：WO2010103529A1

  公开（公告）日：2010-09-16

  A new method for the preparation of solifenacin by reacting quinuclidin-3-ol and bis (aryl) carbonate to form (3R)-l -azabicyclo[2.2.2]oct-3-yl 4-aryl carbonate of formula (IVa); and treating (3R)-I - azabicyclo[2.2.2]oct-3-yl 4-aryl carbonate of formula (IVa) with (1S)- I -phenyl- 1, 2, 3, 4- tetrahydroisoquinoline in an inert atmosphere to form a Solifenacin base which is converted into its pharmaceutically acceptable salts. The invention also provide new compound, (3R)-1 - azabicyclo[2.2.2]oct-3-yl 4-aryl carbonate, which is used as an intermediate for the preparation of Solifenacin base and a process for the preparation thereof.

  一种通过将quinuclidin-3-ol和双(芳基)碳酸酯反应以形成式(IVa)的(3R)-1-azabicyclo[2.2.2]辛-3-基4-芳基碳酸酯来制备索利那新的方法；并在惰性气氛中处理式(IVa)的(3R)-1-azabicyclo[2.2.2]辛-3-基4-芳基碳酸酯，与(1S)-1-苯基-1,2,3,4-四氢异喹啉反应，形成转化为其药用可接受盐的索利那新碱。该发明还提供了新化合物(3R)-1-azabicyclo[2.2.2]辛-3-基4-芳基碳酸酯，用作制备索利那新碱的中间体及其制备方法。
• METHOD FOR THE PREPARATION OF SOLIFENACIN AND INTERMEDIATE THEREOF
  申请人：Mathad Vijayvitthal Thippannachar

  公开号：US20110319621A1

  公开（公告）日：2011-12-29

  A method for the preparation of solifenacin by reacting quinuclidin-3-ol and bis(aryl) carbonate to form (3R)-1-azabicyclo[2.2.2]oct-3-yl 4-aryl carbonate of formula (IVa); and treating (3R)-1-azabicyclo[2.2.2]oct-3-yl 4-aryl carbonate of formula (IVa) with (1S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline of formula (V) in an inert atmosphere to form a Solifenacin base, which is converted into its pharmaceutically acceptable salts. The invention also provides a compound, (3R)-1-azabicyclo[2.2.2]oct-3-yl 4-aryl carbonate of formula (IVa), which is used as an intermediate for the preparation of Solifenacin base and a process for the preparation thereof.

  一种制备索利那新的方法，通过反应三氢喹啉醇和双(芳基)碳酸酯生成公式(IVa)的(3R)-1-氮杂双环[2.2.2]辛-3-基4-芳基碳酸酯; 并在惰性气氛下处理公式(IVa)的(3R)-1-氮杂双环[2.2.2]辛-3-基4-芳基碳酸酯和公式(V)的(1S)-1-苯基-1,2,3,4-四氢异喹啉，形成索利那新碱，再转化为其药学上可接受的盐。本发明还提供一种化合物，公式为(IVa)的(3R)-1-氮杂双环[2.2.2]辛-3-基4-芳基碳酸酯，用作制备索利那新碱的中间体以及其制备方法。
• POLYCARBONATE-BASE POLYMER, PRODUCTION PROCESS, RESIN COATING FLUID PREPARED THEREFROM, AND ELECTROPHOTOGRAPHIC PHOTORECEPTOR PREPARED THEREFROM
  申请人：IDEMITSU KOSAN COMPANY LIMITED

  公开号：EP0837085A1

  公开（公告）日：1998-04-22

  A polymer comprising mainly repeating units (1) and/or repeating units (2), containing optionally terminal groups (3) and/or repeating units (4), and having a reduced viscosity [ηsp/c] of 0.2 to 10.0 dl/g as measured in a 0.5 g/dl solution thereof in methylene chloride at 20°C; a resin coating fluid containing the polymer, a charge-transfer substance and a solvent; and an electrophotographic photoreceptor containing the polymer as a binder resin in a photosensitive layer, wherein Rf1 represents a group that is composed of at least carbon atoms and fluorine atoms and bonded directly to the two oxygen atoms of the carbonate linkage in the general formula (1) without any intervening arylene group; and Rf2 represents a group that is composed of at least carbon atoms and fluorine atoms and bonded directly to one of the oxygen atoms of the carbonate linkage in the general formula (3) without any intervening arylene group.

  一种主要由重复单元（1）和/或重复单元（2）组成的聚合物，含有任选的末端基团（3）和/或重复单元（4），在 0.其中 Rf1 代表至少由碳原子和氟原子组成并直接与通式（1）中碳酸酯连接的两个氧原子键合的基团，而没有任何芳基介入；Rf2 代表一个至少由碳原子和氟原子组成的基团，直接与通式（3）中碳酸酯链节的一个氧原子键合，中间不含任何芳烯基。