2-Butenoic acid, 4-methylphenyl ester, (E)- | 138123-48-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2-Butenoic acid, 4-methylphenyl ester, (E)-
• 英文别名: (4-methylphenyl) but-2-enoate
• CAS: 138123-48-5
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: FGJQFRNEXKYBQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenyl-1H-pyrrolo[2,3-b]pyridine 、 2-Butenoic acid, 4-methylphenyl ester, (E)- 在 tris(acetonitrile)pentamethylcyclopentadienylrhodium(III) hexafluoroantimonate 、 copper(II) acetate monohydrate 、 溶剂黄146 作用下， 以 乙二醇二甲醚 为溶剂， 反应 80.0h， 以70%的产率得到p-tolyl 2-(6-methyl-6H-pyrido[3',2':4,5]pyrrolo[1,2-a]indol-6-yl)acetate
  参考文献：
  名称：

  铑催化串联成环通过双C与缺电子的烯烃7氮杂吲哚的反应？H激活

  摘要：

  铑通过烯化反应和随后的分子内C-Michael型环化反应进行串联环化反应是直接构建CC键的有效方法。简单而原子经济的策略可从7-氮杂吲哚和烯烃中生成具有季碳中心的7-氮杂吲哚的各种烷基化衍生物。

  DOI：

  10.1002/adsc.201600112
• 作为产物：
  描述：

  对甲酚 、 巴豆酰氯 在 sodium hydride 作用下， 生成 2-Butenoic acid, 4-methylphenyl ester, (E)-
  参考文献：
  名称：

  TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes: A novel method for the solid-phase synthesis of dihydrocoumarins and coumarins

  摘要：

  TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes was performed using polystyrene-supported succinimidyl selenide as the selenium source. This catalytic process provides an efficient method for the regioselective synthesis of dihydrocoumarins possessing a seleno-functionality, followed by traceless cleavage of selenium linker to provide dihydrocoumarins and coumarins in good yields and purities. (C) 2012 E Tang. Published by Elsevier B.V on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2012.03.022

文献信息

• Michael Addition of Active Methylene Compounds to α,β-Unsaturated Carbonyl Compounds under the Influence of Molecular Sieves in Dimethyl Sulfoxide
  作者：Tomoko Kakinuma、Ryoichi Chiba、Takeshi Oriyama

  DOI：10.1246/cl.2008.1204

  日期：2008.12.5

  The Michael addition of active methylene compounds to α,β-unsaturated carbonyl compounds in the presence of MS 4A in dimethyl sulfoxide proceeds smoothly to afford the corresponding 1,4-addition pr...

  在MS 4A的存在下，活性亚甲基化合物与α,β-不饱和羰基化合物在二甲亚砜中的迈克尔加成反应顺利进行，得到相应的1,4-加成反应...
• Asymmetric Sulfa-Michael Addition of α,β-Unsaturated Esters/Amides Using a Chiral N-Heterocyclic Carbene as a Noncovalent Organocatalyst
  作者：Jiean Chen、Yong Huang、Pengfei Yuan、Sixuan Meng

  DOI：10.1055/s-0035-1561843

  日期：——

  We report an asymmetric sulfa-Michael reaction of α,β-unsaturated amides and esters using a chiral N-heterocyclic carbene as the HOMO-raising organocatalyst. We discovered an interesting correlation between 13C NMR shifts of substrates and ee of their products. More electron-deficient Michael acceptors afforded higher enantioselectivity.

  我们报告了使用手性 N-杂环卡宾作为 HOMO 提升有机催化剂的 α,β-不饱和酰胺和酯的不对称磺胺-迈克尔反应。我们发现底物的 13C NMR 位移与其产物的 ee 之间存在有趣的相关性。更多缺电子迈克尔受体提供更高的对映选择性。
• Rhodium-Catalyzed Tandem Annulation Reactions of 7-Azaindoles with Electron-Deficient Olefins<i>via</i>Double CH Activation
  作者：Shuai-Shuai Li、Hui Lin、Chen-Fei Liu、Ying-Qi Xia、Xiao-Mei Zhang、Lin Dong

  DOI：10.1002/adsc.201600112

  日期：2016.5.19

  Rhodium‐catalyzed tandem annulation reactions via olefination and subsequent intramolecular C‐Michael‐type cyclization represent an efficient approach for the direct construction of CC bonds. The simple and atom‐economic strategy produces various alkylation derivatives of 7‐azaindole with a quaternary carbon center from 7‐azaindoles and olefins.

  铑通过烯化反应和随后的分子内C-Michael型环化反应进行串联环化反应是直接构建CC键的有效方法。简单而原子经济的策略可从7-氮杂吲哚和烯烃中生成具有季碳中心的7-氮杂吲哚的各种烷基化衍生物。
• Direct Dehydrogenative Access to Unsymmetrical Phenones
  作者：Congjun Yu、Raolin Huang、Frederic W. Patureau

  DOI：10.1002/anie.202201142

  日期：2022.5.9

  The Friedel–Crafts reaction is an emblematic method for constructing C−C bonds at aromatic positions. Rendering this reaction dehydrogenative on a broad scope of substrates under simple reaction conditions constitutes an important milestone for synthetic chemistry.

  弗里德尔-克来福特反应是在芳香位置构建 C−C 键的标志性方法。在简单的反应条件下使该反应在广泛的底物上发生脱氢，是合成化学的一个重要里程碑。
• TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes: A novel method for the solid-phase synthesis of dihydrocoumarins and coumarins
  作者：E Tang、Wen Li、Zhang Yong Gao、Xi Gu

  DOI：10.1016/j.cclet.2012.03.022

  日期：2012.6

  TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes was performed using polystyrene-supported succinimidyl selenide as the selenium source. This catalytic process provides an efficient method for the regioselective synthesis of dihydrocoumarins possessing a seleno-functionality, followed by traceless cleavage of selenium linker to provide dihydrocoumarins and coumarins in good yields and purities. (C) 2012 E Tang. Published by Elsevier B.V on behalf of Chinese Chemical Society. All rights reserved.