(E)-3-methoxy-4-trifluoromethylsulfonyloxycinnamaldehyde | 1030842-36-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: (E)-3-methoxy-4-trifluoromethylsulfonyloxycinnamaldehyde
• 英文别名: (E)-3-methoxy-4-trifluoromethylsulfonyloxy-cinnamaldehyde；[2-methoxy-4-[(E)-3-oxoprop-1-enyl]phenyl] trifluoromethanesulfonate
• CAS: 1030842-36-4
• 化学式: C₁₁H₉F₃O₅S
• 分子量: 310.251
• InChiKey: PNCQZPBXCSZWCP-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (E)-3-methoxy-4-trifluoromethylsulfonyloxycinnamaldehyde 、 亚硝基苯 在 potassium tert-butylate 、 1,3-双(2,6-二异丙基苯基)氯化咪唑鎓 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 2-methoxy-4-(5-oxo-2-phenylisoxazolidin-3-yl)phenyl trifluoromethanesulfonate
  参考文献：
  名称：

  Organocatalytic Synthesis of N-Phenylisoxazolidin-5-ones and a One-Pot Synthesis of β-Amino Acid Esters

  摘要：

  A novel N-heterocyclic carbene (NHC)-catalyzed C-N bond formation by the reaction of alpha,beta-unsaturated aldehydes and nitrosobenzene to N-phenylisoxazolidin-5-ones, followed by an acid-catalyzed esterification and Bamberger-like rearrangement in a mild one-pot protocol leads to N-p-methoxyphenyl (N-PMP) protected beta-amino acid esters.

  DOI：

  10.1021/ol800003n
• 作为产物：
  描述：

  三氟甲磺酸酐 、 Coniferaldehyde 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-3-methoxy-4-trifluoromethylsulfonyloxycinnamaldehyde
  参考文献：
  名称：

  [EN] N-HETEROCYCLIC CARBENE CATALYZED SYNTHESIS OF N-PHENYLISOXAZOLIDIN-5-ONE DERIVATIVE AND SYNTHESIS OF ß -AMINO ACID ESTER DERIVATIVE
  [FR] SYNTHÈSE DE CARBÈNE N-HÉTÉROCYCLIQUE CATALYSÉ D'UN DÉRIVÉ DE N-PHÉNYLISOXAZOLIDINE-5-ONE ET SYNTHÈSE D'UN DÉRIVÉ D'ESTER DE ß-ACIDE AMINÉ

  摘要：

  公开号：

  WO2008115149A9

文献信息

• N-HETEROCYCLIC CARBENE CATALYZED SYNTHESIS OF N-PHENYLISOXAZOLIDIN-5-ONE DERIVATIVE AND SYNTHESIS OF β-AMINO ACID ESTER DERIVATIVE
  申请人：Zhang Yugen

  公开号：US20100099886A1

  公开（公告）日：2010-04-22

  A process for preparing a N-phenylisoxazolidin-5-one derivative is provided. The process for preparing the N-phenylisoxazolidin-5-one derivative comprises reacting an α,β-unsaturated aldehyde with nitrosobenzene in the presence of a N-heterocyclic carbene (NHC) catalyst. A process for preparing an N-alkoxyphenyl protected β-amino acid ester derivative is further provided. The process for preparing the N-alkoxyphenyl protected β-amino acid ester derivative comprises reacting an α,β-unsaturated aldehyde with nitrosobenzene in the presence of a N-heterocyclic carbene (NHC) catalyst to form a N-phenylisoxazolidin-5-one derivative, and then treating the N-phenylisoxazolidin-5-one derivative with an alcohol in the presence of an acid catalyst. A process for preparing an N-alkoxyphenyl protected β-amino acid ester derivative, comprising treating a N-phenylisoxazolidin-5-one derivative with an alcohol in the presence of an acid catalyst, is also provided.

  提供一种制备N-苯基异噁唑烷-5-酮衍生物的方法。制备N-苯基异噁唑烷-5-酮衍生物的方法包括在N-杂环卡宾（NHC）催化剂的存在下，将α，β-不饱和醛与亚硝基苯反应。进一步提供一种制备N-烷氧基苯基保护的β-氨基酸酯衍生物的方法。制备N-烷氧基苯基保护的β-氨基酸酯衍生物的方法包括在N-杂环卡宾（NHC）催化剂的存在下，将α，β-不饱和醛与亚硝基苯反应以形成N-苯基异噁唑烷-5-酮衍生物，然后在酸催化剂的存在下用醇处理N-苯基异噁唑烷-5-酮衍生物。还提供了一种制备N-烷氧基苯基保护的β-氨基酸酯衍生物的方法，包括在酸催化剂的存在下用醇处理N-苯基异噁唑烷-5-酮衍生物。
• N-HETEROCYCLIC CARBENE (NHC) CATALYZED SYNTHESIS OF HYDROXAMIC ACIDS
  申请人：Zhang Yugen

  公开号：US20100105921A1

  公开（公告）日：2010-04-29

  A process for preparing hydroxamic acids is provided. The process comprises reacting an aldehyde with a nitroso compound in the presence of a N-heterocyclic carbene (NHC) catalyst.

  提供了一种制备羟肟酸的过程。该过程包括在N-杂环卡宾（NHC）催化剂的存在下将醛与亚硝基化合物反应。
• Synthesis, crystal structures, spectroscopic characterization and in vitro evaluation of the 4-sulfono-3-methoxycinnamaldehydes as potential α-glucosidase and/or α-amylase inhibitors
  作者：Terrinne P. Mokoena、Marole M. Maluleka、Richard M. Mampa、Malose J. Mphahlele、Bernice A. Monchusi

  DOI：10.1016/j.molstruc.2022.134119

  日期：2023.1

  crystal lattices of these compounds. Their potential to inhibit α-glucosidase and/or α-amylase activities were evaluated through enzymatic assays in vitro complemented with molecular docking studies. 4-(Methoxyphenyl)sulfono-3-methoxycinnamaldehyde (2d) exhibited increased inhibitory effect against α-glucosidase (IC50 = 0.68 ± 1.36 µM) and α-amylase (IC50 = 22.99 ± 0.45 µM) compared to substrate 1 (IC50 = 1

  4-sulfono-3-methoxycinnamaldehyde 衍生物2a - e由 4-hydroxy-3-methoxycinnamaldehyde 1与烷基或苯基磺酰氯磺化合成。单晶 X 射线衍射 (XRD) 和1 H NMR 光谱技术都提供了这些分子结构的 α,β-不饱和羰基臂的反式立体化学的证据。XRD方法证实反式异构体仅以固态存在。另一方面，NOESY 实验证实了在溶液相中还存在具有顺式烯基部分和反式的构象异构体醛基的取向。这一观察得到了密度泛函理论研究的证实，该研究预测了气相中顺式和反式异构体的共存。Hirshfeld 表面和 2D 指纹图用于了解导致这些化合物晶格中分子堆积的分子间相互作用。它们抑制α-葡萄糖苷酶和/或α-淀粉酶活性的潜力通过体外酶测定和分子对接研究进行了评估。4-(Methoxyphenyl)sulfono-3-methoxycinnamaldehyde
• N-Heterocyclic Carbene (NHC)-Catalyzed Direct Amidation of Aldehydes with Nitroso Compounds
  作者：Fong Tian Wong、Pranab K. Patra、Jayasree Seayad、Yugen Zhang、Jackie Y. Ying

  DOI：10.1021/ol8004276

  日期：2008.6.1

  NHC-catalyzed direct amidation of aldehydes with nitroso compounds is a powerful method for the synthesis of N-arylhydroxamic acids. A variety of aryl, alkyl, alkenyl, and heterocyclic aldehydes were found to give excellent yields of the corresponding N-arylhydroxamic acids. This chemistry was also extended to the synthesis of chiral N-arylhydroxamic acids by kinetic resolution of a-branched aldehydes, a domino amidation-redox amination reaction of acrolein, and a three-component reaction for the synthesis of N-arylaziridines.
• WO2008/115153
  申请人：——

  公开号：——

  公开（公告）日：——