ethyl 3-phenyl-3-(4-(trifluoromethyl)phenyl)propanoate | 1413859-30-9

• 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: ethyl 3-phenyl-3-(4-(trifluoromethyl)phenyl)propanoate
• 英文别名: ethyl (3R)-3-phenyl-3-[4-(trifluoromethyl)phenyl]propanoate
• CAS: 1413859-30-9
• 化学式: C₁₈H₁₇F₃O₂
• 分子量: 322.327
• InChiKey: QQAZHGDBZLZGDW-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (Z)-ethyl 3-phenyl-3-(4-(trifluoromethyl)phenyl)acrylate 在 甲基二乙氧基硅烷 、 C₂₂H₃₁N₂O₇Rh 、 盐酸 作用下， 以 甲苯 、 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 以96%的产率得到ethyl 3-phenyl-3-(4-(trifluoromethyl)phenyl)propanoate
  参考文献：
  名称：

  Enantioselective Synthesis of Optically Active 3,3-Diarylpropanoates by Conjugate Hydrosilylation with Chiral Rh-bis(oxazolinyl)phenyl Catalysts

  摘要：

  Conjugate hydrosilylation of 3,3-diarylacrylate derivatives catalyzed by chiral rhodium-bis(oxazolinyl)phenyl complexes (1 mol %) at 60 degrees C for 2 h was investigated to prepare optically active 3,3-diarylpropanoate derivatives in high yields up to 99% yield and high enantioselectivities up to 99%.

  DOI：

  10.1021/jo302357b

文献信息

• Enantioselective β-C(sp³)–H arylation of amides<i>via</i>synergistic nickel and photoredox catalysis
  作者：Wu Zhang、Xiaomin Shu、Leitao Huan、Buqing Cheng、Haohua Huo

  DOI：10.1039/d1ob01774h

  日期：——

  An enantioselective benzylic β-C(sp3)–H arylation of amides via synergistic nickel and photoredox catalysis is reported. The C–H bond is activated by a bromine-radical-mediated C–H cleavage. This mild yet straightforward protocol provides arylation products in up to 96% yield and with up to 95% ee.

  报道了通过协同镍和光氧化还原催化对酰胺的对映选择性苄基 β-C(sp 3 )-H 芳基化。C-H 键被溴自由基介导的 C-H 裂解激活。这种温和而直接的方案可提供高达 96% 的收率和高达 95% ee 的芳基化产物。
• Rh-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to 3-Arylpropenoates: Enantioselective Synthesis of (R)-Tolterodine
  作者：Valerio Zullo、Anna Iuliano

  DOI：10.1002/ejoc.201801690

  日期：2019.2.14

  Deoxycholic acid derived binaphthyl phosphites promote a highly enantioselective Rh‐catalyzed conjugate addition of arylboronic acids to 3‐arylpropenoates, giving useful chiral building blocks for the synthesis of biologically active compounds. The protocol was successfully applied to the enantioselective synthesis of the antimuscarinic drug (R)‐tolterodine.

  脱氧胆酸衍生的亚萘基亚磷酸酯可将芳基硼酸高度对映体的Rh催化的Rh催化共轭加成到3-芳基丙酸酯中，为合成生物活性化合物提供了有用的手性结构单元。该协议已成功应用于抗毒蕈碱药物（R）-托特罗定的对映选择性合成。
• Enantioselective Synthesis of Optically Active 3,3-Diarylpropanoates by Conjugate Hydrosilylation with Chiral Rh-bis(oxazolinyl)phenyl Catalysts
  作者：Kengou Itoh、Ayae Tsuruta、Jun-ichi Ito、Yoshihiko Yamamoto、Hisao Nishiyama

  DOI：10.1021/jo302357b

  日期：2012.12.7

  Conjugate hydrosilylation of 3,3-diarylacrylate derivatives catalyzed by chiral rhodium-bis(oxazolinyl)phenyl complexes (1 mol %) at 60 degrees C for 2 h was investigated to prepare optically active 3,3-diarylpropanoate derivatives in high yields up to 99% yield and high enantioselectivities up to 99%.