3-[(Z)-2-chloro-2,2-difluoro-1-(4-methoxyanilino)ethylidene]tetrahydro-2-furanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-[(Z)-2-chloro-2,2-difluoro-1-(4-methoxyanilino)ethylidene]tetrahydro-2-furanone
• 英文别名: (3Z)-3-[2-chloro-2,2-difluoro-1-(4-methoxyanilino)ethylidene]oxolan-2-one
• 化学式: C₁₃H₁₂ClF₂NO₃
• 分子量: 303.693
• InChiKey: DQIHTPJIGYNKOY-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  γ-丁内酯 、 Ethanimidoyl chloride, 2-chloro-2,2-difluoro-N-(4-methoxyphenyl)-, (1Z)- 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到3-[(Z)-2-chloro-2,2-difluoro-1-(4-methoxyanilino)ethylidene]tetrahydro-2-furanone
  参考文献：
  名称：

  N取代的β-烯氨基酸衍生物：氟化β-烯氨基酸酯的新方法

  摘要：

  氟化亚氨基氯化物1与酯烯醇锂2的反应以良好的至优异的产率得到N-取代的γ-氟化的β-烯氨基和/或β-亚氨基酯4。β-烯氨基酯仅作为Z异构体获得。©1997由Elsevier Science Ltd发布。

  DOI：

  10.1016/s0040-4039(97)01549-9

文献信息

• N-Substituted β-Enamino Acid Derivatives: A New Approach to Fluorinated β-Enamino Esters
  作者：Santos Fustero、Belén Pina、Antonio Simón-Fuentes

  DOI：10.1016/s0040-4039(97)01549-9

  日期：1997.9

  Reaction of fluorinated imidoyl chlorides 1 with lithium ester enolates 2 gave N-substituted γ-fluorinated β-enamino and/or β-imino esters 4 in good to excellent yields. β-Enamino esters were obtained exclusively as Z isomers. © 1997 Published by Elsevier Science Ltd.

  氟化亚氨基氯化物1与酯烯醇锂2的反应以良好的至优异的产率得到N-取代的γ-氟化的β-烯氨基和/或β-亚氨基酯4。β-烯氨基酯仅作为Z异构体获得。©1997由Elsevier Science Ltd发布。
• New Strategy for the Stereoselective Synthesis of Fluorinated β-Amino Acids
  作者：Santos Fustero、Belén Pina、Esther Salavert、Antonio Navarro、M. Carmen Ramírez de Arellano、Antonio Simón Fuentes

  DOI：10.1021/jo025621k

  日期：2002.7.1

  Racemic and chiral nonracemic alpha-substituted and alpha-unsubstituted beta-fluoroalkyl beta-amino acid derivatives 6 and 9 have been synthesized in two steps starting from fluorinated imidoyl chlorides 1 and ester enolates. This approach is based on the chemical reduction of previously obtained gamma-fluorinated beta-enamino esters 4 by using ZnI2/NaBH4 in a nonchelated aprotic medium (dry CH2Cl2) as the reducing agent. A metal-chelated six-membered model has been suggested to explain the stereochemical outcome of the reduction reaction. The process takes place with high yields and with moderate to good diastereoselectivity. The best results related to diastereoselective reduction of chiral beta-enamino esters 4 were provided by the use of (-)-8-phenylmenthol as a chiral auxiliary.