ethyl 2-methylene-3-(phenylamino)butanoate | 1392285-91-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: ethyl 2-methylene-3-(phenylamino)butanoate
• 英文别名: Ethyl 3-anilino-2-methylidenebutanoate；ethyl 3-anilino-2-methylidenebutanoate
• CAS: 1392285-91-4
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: TVAHMMHZLCBVFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  惕各酸乙酯 、 苯基羟胺 在 iron(II) chloride tetrahydrate 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以75%的产率得到ethyl 2-methylene-3-(phenylamino)butanoate
  参考文献：
  名称：

  Direct Synthesis of β-Alkyl N-Aryl Aza Baylis–Hillman Adducts via Nitroso-Ene Reaction

  摘要：

  A new approach for the direct Fe-catalyzed synthesis of beta-alkyl N-aryl aza Baylis-Hillman (ABH) adducts is reported. This approach involves the formation of a C-N bond via a nitroso-ene reaction. This is a simple, fast, and best alternate method to overcome the substrate scope limitations of the ABH reaction, which converts allyl esters and carbonyl compounds to novel ABH adducts. A variety of arylhydroxylamines reacted with esters, aldehydes, ketone, and nitriles to yield the corresponding products in moderate to excellent yields.

  DOI：

  10.1021/jo301266f

文献信息

• [EN] METHOD OF PRODUCING CHIRAL N-SUBSTITUTED ALLYLIC AMINE COMPOUNDS<br/>[FR] PROCÉDÉ DE PRODUCTION DE COMPOSÉS CHIRAUX D'AMINES ALLYLIQUES N-SUBSTITUÉES
  申请人：UNIV LOUISIANA AT LAFAYETTE

  公开号：WO2014025927A1

  公开（公告）日：2014-02-13

  The method relates to the field of asymmetric allylic amination and comprises preparing a chiral N-substituted allylic amine compound from the corresponding allylic substrates and substituted hydroxylamines, in the presence of a catalyst, said catalyst comprising copper compounds and a chiral ligand. Examples of chiral amine compounds which can be made using the method include Vigabatrin, Ezetimibe Terbinafme, Naftifme 3-methylmorphine, Sertraline, Cinacalcet, Mefloquine hydrochloride, and Rivastigmine. There are over 20,000 known bioactive molecules with chiral N-substituted allylic amine substructure. The method may also be used to produce non-natural chiral B-aminoacid esters, a sub-class of chiral N-substituted allylic amine compounds. Examples of B-aminoacid ester which can be produced by the disclosed method, include, but are not limited to, N-(2-methylpent-l-en-3-yl)benzenamine and Ethyl 2-methylene-3-(phenylamino)butanoate. Further, the products of the method described herein can be used to produce chiral heterocycles and bioactive molecules or materials.

  该方法涉及不对称烯丙基胺化领域，包括在催化剂的存在下，从相应的烯丙基底物和取代的羟胺制备手性N-取代烯丙基胺化合物，所述催化剂包括铜化合物和手性配体。使用该方法可以制备的手性胺化合物的示例包括维加巴林、依泽替米贝、特比那芬、那非那芬、3-甲基吗啡、舍曲林、西那卡塞、盐酸美氟喹和利伐司特。已知具有手性N-取代烯丙基胺亚结构的生物活性分子超过20,000种。该方法还可用于生产非天然手性B-氨基酸酯，这是手性N-取代烯丙基胺化合物的一个亚类。通过所披露的方法可以生产的B-氨基酸酯的示例包括N-(2-甲基戊-1-烯-3-基)苯胺和乙酸乙酯2-亚甲基-3-(苯氨基)丁酸酯。此外，所述方法的产物可用于生产手性杂环化合物和生物活性分子或材料。
• COMPOSITION OF MATTER
  申请人：University of Louisiana at Lafayette

  公开号：US20160304538A1

  公开（公告）日：2016-10-20

  The method relates to the field of asymmetric allylic amination and comprises preparing a chiral N-substituted allylic amine compound from the corresponding allylic substrates and substituted hydroxylamines, in the presence of a catalyst, said catalyst comprising copper compounds and a chiral ligand. Examples of chiral amine compounds which can be made using the method include Vigabatrin, Ezetimibe Terbinafine, Naftifine 3-methylmorphine, Sertraline, Cinacalcet, Mefloquine hydrochloride, and Rivastigmine. There are over 20,000 known bioactive molecules with chiral N-substituted allylic amine substructure. The method may also be used to produce non-natural chiral β-aminoacid esters, a sub-class of chiral N-substituted allylic amine compounds. Examples of β-aminoacid ester which can be produced by the disclosed method, include, but are not limited to, N-(2-methylpent-1-en-3-yl)benzenamine and Ethyl 2-methylene-3-(phenylamino)butanoate. Further, the products of the method described herein can be used to produce chiral heterocycles and bioactive molecules or materials. A novel chiral copper-BINAM nitrosoarene complex is also set forth.

  该方法涉及不对称联烯胺化领域，包括在催化剂的存在下，从相应的联烯底物和取代羟胺制备手性N-取代联烯胺化合物，所述催化剂包括铜化合物和手性配体。使用该方法可以制备的手性胺化合物的示例包括Vigabatrin、Ezetimibe Terbinafine、Naftifine 3-methylmorphine、Sertraline、Cinacalcet、Mefloquine hydrochloride和Rivastigmine。已知具有手性N-取代联烯胺亚结构的生物活性分子超过20,000种。该方法还可用于生产非天然手性β-氨基酸酯，是手性N-取代联烯胺化合物的一个子类。公开方法可以生产的β-氨基酸酯的示例包括但不限于N-(2-甲基戊-1-烯-3-基)苯胺和乙酸乙酯2-亚甲基-3-(苯胺基)丁酸酯。此外，所述方法的产物可用于生产手性杂环和生物活性分子或材料。还提出了一种新型手性铜-BINAM硝基芳烃配合物。
• Chiral N-substituted allylic amine compounds
  申请人：University of Louisiana at Lafayette

  公开号：US10179330B2

  公开（公告）日：2019-01-15

  The method relates to the field of asymmetric allylic amination and comprises preparing a chiral N-substituted allylic amine compound from the corresponding allylic substrates and substituted hydroxylamines, in the presence of a catalyst, said catalyst comprising copper compounds and a chiral ligand. Examples of chiral amine compounds which can be made using the method include Vigabatrin, Ezetimibe Terbinafine, Naftifine 3-methylmorphine, Sertraline, Cinacalcet, Mefloquine hydrochloride, and Rivastigmine. There are over 20,000 known bioactive molecules with chiral N-substituted allylic amine substructure. The method may also be used to produce non-natural chiral β-aminoacid esters, a sub-class of chiral N-substituted allylic amine compounds. Examples of β-aminoacid ester which can be produced by the disclosed method, include, but are not limited to, N-(2-methylpent-1-en-3-yl)benzenamine and Ethyl 2-methylene-3-(phenylamino)butanoate. Further, the products of the method described herein can be used to produce chiral heterocycles and bioactive molecules or materials. A novel chiral copper-ligand nitrosoarene complex is also set forth.

  该方法涉及不对称烯丙基胺化领域，包括在催化剂存在下，由相应的烯丙基底物和取代的羟胺制备手性 N-取代烯丙基胺化合物，所述催化剂包括铜化合物和手性配体。使用该方法可制备的手性胺化合物包括维加巴曲林、依泽替米贝-特比萘芬、萘替芬-3-甲基吗啡、舍曲林、西那考酮、盐酸甲氟喹和利伐斯的明。目前已知的具有手性 N-取代烯丙基胺亚基结构的生物活性分子超过 20,000 种。该方法还可用于生产非天然手性 β-氨基酸酯，这是手性 N-取代烯丙基胺化合物的一个亚类。可通过所公开的方法生产的 β-氨基酸酯的例子包括但不限于 N-(2-甲基戊-1-烯-3-基)苯胺和 2-亚甲基-3-(苯基氨基)丁酸乙酯。此外，本文所述方法的产物可用于生产手性杂环和生物活性分子或材料。还提出了一种新型手性铜配体亚硝基炔络合物。
• METHOD OF PRODUCING CHIRAL N-SUBSTITUTED ALLYLIC AMINE COMPOUNDS
  申请人：UNIVERSITY OF LOUISIANA AT LAFAYETTE

  公开号：US20150259276A1

  公开（公告）日：2015-09-17

  The method relates to the field of asymmetric allylic amination and comprises preparing a chiral N-substituted allylic amine compound from the corresponding allylic substrates and substituted hydroxylamines, in the presence of a catalyst, said catalyst comprising copper compounds and a chiral ligand. Examples of chiral amine compounds which can be made using the method include Vigabatrin, Ezetimibe Terbinafine, Naftifine 3-methylmorphine, Sertraline, Cinacalcet, Mefloquine hydrochloride, and Rivastigmine. There are over 20,000 known bioactive molecules with chiral N-substituted allylic amine substructure. The method may also be used to produce non-natural chiral β-aminoacid esters, a sub-class of chiral N-substituted allylic amine compounds. Examples of β-aminoacid ester which can be produced by the disclosed method, include, but are not limited to, N-(2-methylpent-1-en-3-yl)benzenamine and Ethyl 2-methylene-3-(phenylamino)butanoate. Further, the products of the method described herein can be used to produce chiral heterocycles and bioactive molecules or materials.
• CHIRAL N-SUBSTITUTED ALLYLIC AMINE COMPOUNDS
  申请人：University of Louisiana at Lafayette

  公开号：US20210238200A1

  公开（公告）日：2021-08-05

  The method relates to the field of asymmetric allylic amination and comprises preparing a chiral N-substituted allylic amine compound from the corresponding allylic substrates and substituted hydroxylamines, in the presence of a catalyst, said catalyst comprising copper compounds and a chiral ligand. Examples of chiral amine compounds which can be made using the method include Vigabatrin, Ezetimibe Terbinafine, Naftifine 3-methylmorphine, Sertraline, Cinacalcet, Mefloquine hydrochloride, and Rivastigmine. There are over 20,000 known bioactive molecules with chiral N-substituted allylic amine substructure. The method may also be used to produce non-natural chiral β-aminoacid esters, a sub-class of chiral N-substituted allylic amine compounds. Examples of β-aminoacid ester which can be produced by the disclosed method, include, but are not limited to, N-(2-methylpent-1-en-3-yl)benzenamine and Ethyl 2-methylene-3-(phenylamino)butanoate. Further, the products of the method described herein can be used to produce chiral heterocycles and bioactive molecules or materials. A novel chiral copper-BINAM nitrosoarene complex is also set forth.