Methyl 2-phenylethenyl carbonate | 1448441-24-4

• 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 2-phenylethenyl carbonate
• CAS: 1448441-24-4
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: OBHGHWZEROPLSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  Methyl 2-phenylethenyl carbonate 在 二(氰基苯)二氯化钯 、 silver(I) nitrite 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 copper(II) choride dihydrate 、 氧气 、 (±)-MonoPhos 作用下， 以 四氢呋喃 、 硝基甲烷 、 叔丁醇 为溶剂， 20.0~500.0 ℃ 、101.33 kPa 条件下， 反应 20.0h， 生成 (R)-3-phenyl-3-(2-methylphenoxy)propanal
  参考文献：
  名称：

  催化剂控制的瓦克型氧化：轻松获得功能化醛

  摘要：

  在烯丙基和高烯丙基位置带有不同氧基团的烯烃的醛选择性氧化是通过亚硝酸盐改性的瓦克氧化完成的。容易获得的含氧烯烃以高达 88% 的醛收率和高达 97% 的醛选择性被氧化。醛选择性氧化能够快速、对映选择性地合成一种重要的药剂托莫西汀。最后，探讨了近端官能团对这种反马尔科夫尼科夫反应的影响，提供了重要的初步机制见解。

  DOI：

  10.1021/ja411749k
• 作为产物：
  描述：

  cinnamic alcohol 、 碳酸二甲酯 在 manganese(II)carbonate 作用下， 反应 15.0h， 以91%的产率得到Methyl 2-phenylethenyl carbonate
  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

• Ruthenium-catalyzed Ortho-selective Aromatic C–H Alkenylation with Alkenyl Carbonates
  作者：Yohei Ogiwara、Takuya Kochi、Fumitoshi Kakiuchi

  DOI：10.1246/cl.140006

  日期：2014.5.5

  Ortho-selective aromatic C–H alkenylation with alkenyl carbonates proceeds in the presence of a catalytic amount of [Ru(cod)(cot)]. Arylpyridines and an aryloxazoline were regioselectively alkenylated without adding external bases. Aromatic C–H alkylation also occurs depending on the reaction conditions.

  在催化剂[Ru(cod)(cot)]的存在下，选择性地对芳香C–H进行烯烃化，使用烯烃碳酸酯。芳基吡啶和芳基噁唑啉在不添加外部碱的情况下进行了区域选择性的烯烃化。芳香C–H烷基化也会根据反应条件发生。
• Catalyst-Controlled Wacker-Type Oxidation: Facile Access to Functionalized Aldehydes
  作者：Zachary K. Wickens、Kacper Skakuj、Bill Morandi、Robert H. Grubbs

  DOI：10.1021/ja411749k

  日期：2014.1.22

  The aldehyde-selective oxidation of alkenes bearing diverse oxygen groups in the allylic and homoallylic position was accomplished with a nitrite-modified Wacker oxidation. Readily available oxygenated alkenes were oxidized in up to 88% aldehyde yield and as high as 97% aldehyde selectivity. The aldehyde-selective oxidation enabled the rapid, enantioselective synthesis of an important pharmaceutical

  在烯丙基和高烯丙基位置带有不同氧基团的烯烃的醛选择性氧化是通过亚硝酸盐改性的瓦克氧化完成的。容易获得的含氧烯烃以高达 88% 的醛收率和高达 97% 的醛选择性被氧化。醛选择性氧化能够快速、对映选择性地合成一种重要的药剂托莫西汀。最后，探讨了近端官能团对这种反马尔科夫尼科夫反应的影响，提供了重要的初步机制见解。
• MnCO3-Catalyzed Transesterification of Alcohols with Dimethyl Carbonate Under Mild Conditions
  作者：Xiuru Bi、Nan Yao、Xu Meng、Mingxia Gou、Peiqing Zhao

  DOI：10.1007/s10562-020-03310-z

  日期：2021.2

  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].