二苯甲基甲基碳酸酯 | 85926-25-6

• 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: 二苯甲基甲基碳酸酯
• 英文名称: diphenylmethyl methyl carbonate
• 英文别名: benzhydryl methyl carbonate；Diphenyl dimethyl carbonate
• CAS: 85926-25-6
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: RASSFDIDKRUSGL-UHFFFAOYSA-N

物化性质

• 沸点：
  343.4±31.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-联苯硼酸 、 二苯甲基甲基碳酸酯 在 bis(η3-allyl-μ-chloropalladium(II)) 、 1,5-双(二苯基膦)戊烷 、 potassium carbonate 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 48.0h， 以77%的产率得到2-(diphenylmethyl)biphenyl
  参考文献：
  名称：

  Suzuki-Miyaura Coupling of Diarylmethyl Carbonates with Arylboronic Acids:  A New Access to Triarylmethanes

  摘要：

  Suzuki-Miyaura coupling of diarylmethyl carbonates with arylboronic acids proceeded in the presence of [Pd(eta(3)-C3H5)Cl](2)-DPPPent (1,5-bis(diphenylphosphino)pentane) catalyst, yielding a variety of triarylmethanes.

  DOI：

  10.1021/ol800078j
• 作为产物：
  描述：

  二苯甲醇 、 碳酸二甲酯 在 manganese(II)carbonate 作用下， 反应 15.0h， 以50%的产率得到二苯甲基甲基碳酸酯
  参考文献：
  名称：

  MnCO3-Catalyzed Transesterification of Alcohols with Dimethyl Carbonate Under Mild Conditions

  摘要：

  Dimethyl carbonate (DMC) is a valuable green reagent with versatile and tunable chemical reactivity and can be used as a raw material for transesterification of alcohols. Herein, MnCO3 was found to be an efficient heterogeneous catalyst for transesterification of various alcohols with DMC and gave desired products under mild conditions. The MnCO3 catalysts were fully characterized by XRD, BET, SEM, TEM, FT-IR and NH3-TPD. The analysis results indicated that MnCO3 calcined at 300 degrees C has significantly enhanced surface area and abundant weak acid sites, which contributed to the superior catalytic performance in the transesterification. Furthermore, deactivation of catalyst resulted from the change of crystal structure and the decrease of weak acid sites. This research expands the potential application for DMC in green chemistry.[GRAPHICS].

  DOI：

  10.1007/s10562-020-03310-z

文献信息

• Visible‐Light‐Enabled Carboxylation of Benzyl Alcohol Derivatives with CO ₂ Using a Palladium/Iridium Dual Catalyst
  作者：Yushu Jin、Naoyuki Toriumi、Nobuharu Iwasawa

  DOI：10.1002/cssc.202102095

  日期：2022.2.8

  Double trouble: A highly efficient visible-light-enabled carboxylation of benzyl alcohol derivatives using CO2 is achieved with a Pd/Ir dual catalyst. A variety of benzyl carboxylic acids and esters can be prepared from the corresponding benzyl alcohol derivatives with high efficiency. By changing the Pd catalyst, switchable site-selective carboxylation between benzylic C−O and aryl C−Cl moieties is

  双重麻烦：使用Pd/Ir 双催化剂实现了使用 CO 2对苯甲醇衍生物进行高效可见光羧化。由相应的苄醇衍生物可以高效地制备多种苄基羧酸和酯。通过改变 Pd 催化剂，可以在苄基 C-O 和芳基 C-Cl 部分之间进行可切换的位点选择性羧化。
• Cleavage of C-C and C-O Bonds to Form C-C Bonds: Direct Cross-Coupling between Acetylenic Alcohols and Benzylic Carbonates
  作者：Zhiyuan Mi、Jiahao Tang、Zhipeng Guan、Wei Shi、Hao Chen

  DOI：10.1002/ejoc.201800861

  日期：2018.8.31

  A palladium‐catalyzed cross‐coupling reaction between C(sp) and C(sp3) centers was achieved in excellent yields via C–C bond cleavage and C–O bond cleavage. The method uses benzylic carbonates and also avoids the involvement of benzyl halides, making it more practical in organic synthesis.

  C（sp）和C（sp 3）中心之间的钯催化交叉偶联反应通过C–C键断裂和C–O键断裂以优异的产率实现。该方法使用碳酸苄基酯，并且避免了苄基卤化物的参与，使其在有机合成中更加实用。
• One-pot carbonyl reduction and carbonate formation using sodium borohydride in dialkyl carbonate solvents
  作者：Abdulakeem Osumah、Jakob Magolan、Kristopher V. Waynant

  DOI：10.1016/j.tetlet.2019.151203

  日期：2019.10

  Preparation of mixed carbonates proceeded in one step from ketones and aldehydes via treatment with NaBH4 in dimethyl or diethyl carbonate solvent at elevated temperatures. This is an efficient and convenient alternative to the traditional two-step sequence of carbonyl reduction to alcohol and subsequent carbonate formation by treatment with an alkyl chloroformate. 25 examples are presented from 49-92% yield

  通过在碳酸二甲酯或二乙基溶剂中用NaBH4处理，从酮和醛中一步制备混合碳酸盐。这是对羰基还原为醇和随后通过用氯甲酸烷基酯处理的随后碳酸盐形成的传统两步序列的有效且方便的替代方法。从49-92％的收率提供了25个实例，突出了该反应的多功能性。
• Palladium-catalyzed Nucleophilic Substitution of Diarylmethyl Carbonates with Malonate Carbanions
  作者：Ryoichi Kuwano、Hiroki Kusano

  DOI：10.1246/cl.2007.528

  日期：2007.4.5

  The nucleophilic substitution of diarylmethyl carbonates with malonate carbanions proceeded in the presence of [Pd(π-C3H5)(cod)]BF4–Cy-Xantphos, giving the desired (diarylmethyl)malonates in up to ...

  在 [Pd(π-C3H5)(cod)]BF4–Cy-Xantphos 存在下，二芳基甲基碳酸酯与丙二酸碳负离子的亲核取代进行，得到所需的（二芳基甲基）丙二酸酯
• Divergent Synthesis of Isonitriles and Nitriles by Palladium-Catalyzed Benzylic Substitution with TMSCN
  作者：Kento Asai、Koji Hirano、Masahiro Miura

  DOI：10.1021/acs.joc.0c01861

  日期：2020.10.2

  Ligand-controlled palladium-catalyzed divergent synthesis of isonitriles and nitriles from benzylic carbonates and TMSCN has been developed. The BINAP- or DPEphos-ligated palladium catalyst selectively provides the corresponding benzylic isonitriles, whereas their regioisomers, benzylic nitriles, are formed exclusively under phosphine ligand-free conditions. Mechanistic studies reveal that isonitrile

  已经开发了由碳酸苄基酯和TMSCN进行配体控制的钯催化的异腈和腈的发散合成。BINAP或DPEphos连接的钯催化剂选择性地提供相应的苄基异腈，而它们的区域异构体苄基腈仅在无膦配体的条件下形成。机理研究表明，在两种条件下，异腈都是主要产物，但在没有辅助膦配体的情况下，它会异构化为腈。