1-phenyl-2-propen-1-yl 4-methoxybenzoate | 27888-36-4

• 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: 1-phenyl-2-propen-1-yl 4-methoxybenzoate
• 英文别名: 1-phenylallyl4-methoxybenzoate；p-Methoxybenzoesaeure-phenyl-1-propen-2-yl-1-ester；1-phenylprop-2-enyl 4-methoxybenzoate
• CAS: 27888-36-4
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: FQMIONABLBSDKN-UHFFFAOYSA-N

物化性质

• 沸点：
  392.9±27.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-phenyl-2-propen-1-yl 4-methoxybenzoate 在 bis(1,5-cyclooctadiene)nickel (0) 、 potassium acetate 、 (2S,4S)-(-)-2,4-双(二苯基磷)戊烷 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 、 二乙二醇二甲醚 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Ni催化氧化膦的不对称烯丙基化

  摘要：

  以高对映选择性实现了用于合成叔氧化膦 (TPO) 的镍催化的仲氧化膦 (SPO) 的不对称烯丙基化。SPO 的动态动力学拆分是在镍配合物的存在下完成的。通过阐明反应的 SPO 起始材料和 TPO 产物的绝对构型，我们确认烯丙基化反应通过 P-立体保留过程进行。该协议代表了通过烯丙基化反应合成 P-立体氧化膦的第一个例子。

  DOI：

  10.1021/jacs.9b08734
• 作为产物：
  描述：

  1-苯基-2-丙烯-1-醇 、 对甲氧基苯甲酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以87%的产率得到1-phenyl-2-propen-1-yl 4-methoxybenzoate
  参考文献：
  名称：

  Kinetic Resolution by Enantioselective Dihydroxylation of Secondary Allylic 4-Methoxybenzoate Esters Using a Mechanistically Designed Cinchona Alkaloid Catalyst

  摘要：

  The OsO4-cinchona alkaloid catalyzed asymmetric dihydroxylation process has been applied successfully to the kinetic resolution of 1-substituted allylic alcohols by the use of the 4-methoxybenzoyl derivatives in conjunction with the specifically designed DHQD-PYDZ(S)-anthryl catalyst (5 . OsO4). Thus, (+/-)-3-buten-2-yl 4-methoxybenzoate (4a) and (+/-)-1-phenyl-2-propen-1-yl 4-methoxybenzoate (4b) have been kinetically resolved with relative rate constants of 20 and 79, respectively. These values are among the best reported for the kinetic resolution of racemic compounds using non-enzymatic catalyst systems. The design of this resolution process was accomplished under mechanistic guidance using the transition state model proposed recently for the asymmetric dihydroxylation process. The specially selected ligand 5 possesses a deep U-shaped binding pocket with both the methoxyquinoline and the 1-anthryl walls projecting rearward of the pyridazine linker group at the floor. This catalyst not only recognizes the 4-methoxybenzoyl group of these substrates, which extends into the distant binding pocket of the catalyst, but also provides an open space adjacent to one of the allylic alpha-substituents of the substrate which allows for enantiomeric selection in the dihydroxylation. The magnitude of the kinetic resolution and the absolute stereopreference for the dihydroxylation reaction provide strong evidence for the guiding mechanistic model. The utility of this process is clearly demonstrated by the selective dihydroxylation of 1,4-pentadien-3-yl 4-methoxybenzoate (10) to give diol 11 in 70% isolated yield with >98% ee and >96% de.

  DOI：

  10.1021/ja00149a004

文献信息

• Pseudo‐Stereodivergent Synthesis of Enantioenriched Tetrasubstituted Alkenes by Cascade 1,3‐Oxo‐Allylation/Cope Rearrangement
  作者：Peng Chen、Yue Li、Zhi‐Chao Chen、Wei Du、Ying‐Chun Chen

  DOI：10.1002/anie.202000044

  日期：2020.4.27

  of highly enantioenriched tetrasubstituted alkene architectures from isatin-based Morita-Baylis-Hillman carbonates and allylic derivatives, under the cooperative catalysis of a tertiary amine and a chiral iridium complex. The success of the switchable construction of the tetrasubstituted alkene motif relies on the diastereodivergent 1,3-oxo-allylation reaction between N-allylic ylides and chiral π-allyliridium

  具有两个或多个立体生成中心的立体异构体的催化非对映异构构型已得到广泛研究。相比之下，尚未认识到将另一种立体成因元素，即涉及多取代的烯烃基团的Z / E构型，可转换地引入光学活性立体异构体中。在此公开的是在叔胺和手性铱配合物的协同催化下，由基于Isatin的Morita-Baylis-Hillman碳酸盐和烯丙基衍生物合成的高度对映体富集的四取代烯烃构筑物的拟立体立体异构体。四取代烯烃基序可转换结构的成功取决于非对映异构体1，
• Meyer,G. et al., Bulletin de la Societe Chimique de France, 1970, p. 730 - 737
  作者：Meyer,G. et al.

  DOI：——

  日期：——
• Kinetic Resolution by Enantioselective Dihydroxylation of Secondary Allylic 4-Methoxybenzoate Esters Using a Mechanistically Designed Cinchona Alkaloid Catalyst
  作者：E. J. Corey、Mark C. Noe、Angel Guzman-Perez

  DOI：10.1021/ja00149a004

  日期：1995.11

  The OsO4-cinchona alkaloid catalyzed asymmetric dihydroxylation process has been applied successfully to the kinetic resolution of 1-substituted allylic alcohols by the use of the 4-methoxybenzoyl derivatives in conjunction with the specifically designed DHQD-PYDZ(S)-anthryl catalyst (5 . OsO4). Thus, (+/-)-3-buten-2-yl 4-methoxybenzoate (4a) and (+/-)-1-phenyl-2-propen-1-yl 4-methoxybenzoate (4b) have been kinetically resolved with relative rate constants of 20 and 79, respectively. These values are among the best reported for the kinetic resolution of racemic compounds using non-enzymatic catalyst systems. The design of this resolution process was accomplished under mechanistic guidance using the transition state model proposed recently for the asymmetric dihydroxylation process. The specially selected ligand 5 possesses a deep U-shaped binding pocket with both the methoxyquinoline and the 1-anthryl walls projecting rearward of the pyridazine linker group at the floor. This catalyst not only recognizes the 4-methoxybenzoyl group of these substrates, which extends into the distant binding pocket of the catalyst, but also provides an open space adjacent to one of the allylic alpha-substituents of the substrate which allows for enantiomeric selection in the dihydroxylation. The magnitude of the kinetic resolution and the absolute stereopreference for the dihydroxylation reaction provide strong evidence for the guiding mechanistic model. The utility of this process is clearly demonstrated by the selective dihydroxylation of 1,4-pentadien-3-yl 4-methoxybenzoate (10) to give diol 11 in 70% isolated yield with >98% ee and >96% de.
• Ni-Catalyzed Asymmetric Allylation of Secondary Phosphine Oxides
  作者：Xu-Teng Liu、Ya-Qian Zhang、Xue-Yu Han、Shi-Ping Sun、Qing-Wei Zhang

  DOI：10.1021/jacs.9b08734

  日期：2019.10.23

  A nickel catalyzed asymmetric allylation of secondary phosphine oxides (SPO) for the synthesis of tertiary phosphine oxides (TPO) was realized with high enantioselectivity. The dynamic kinetic resolution of SPO was accomplished in the presence of nickel complex. By elucidating the absolute configurations of the reacted SPO starting material and the TPO product, we confirmed that the allylation reaction

  以高对映选择性实现了用于合成叔氧化膦 (TPO) 的镍催化的仲氧化膦 (SPO) 的不对称烯丙基化。SPO 的动态动力学拆分是在镍配合物的存在下完成的。通过阐明反应的 SPO 起始材料和 TPO 产物的绝对构型，我们确认烯丙基化反应通过 P-立体保留过程进行。该协议代表了通过烯丙基化反应合成 P-立体氧化膦的第一个例子。