(E)-N-(2-chloro-2,2-difluoroethylidene)-4-methoxyaniline | 863890-27-1

• 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: (E)-N-(2-chloro-2,2-difluoroethylidene)-4-methoxyaniline
• 英文别名: N-(2-chloro-2',2'-difluoroethylidene)-p-methoxyaniline
• CAS: 863890-27-1
• 化学式: C₉H₈ClF₂NO
• 分子量: 219.618
• InChiKey: KHNFADIZOWEIET-AWNIVKPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  21.59
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-戊烯醛 、 (E)-N-(2-chloro-2,2-difluoroethylidene)-4-methoxyaniline 在 L-脯氨酸 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 72.0h， 生成
  参考文献：
  名称：

  An Enantio- and Diastereoselective Synthesis of Fluorinated β-Aminoalkyl­oxepine Derivatives through Mannich and Ring-Closing Metathesis Reactions

  摘要：

  在受保护的氟代二氨和4-戊烯醛之间进行脯氨酸催化曼尼希反应，然后进行还原和选择性O-烯丙基化，得到γ-氨基醚，然后作为环化复分解反应（RCM）的底物，以高度立体和对应选择性方式提供氟化β-氨基烷基氧杂环庚烯。

  DOI：

  10.1055/s-2006-950345
• 作为产物：
  描述：

  Ethanimidoyl chloride, 2-chloro-2,2-difluoro-N-(4-methoxyphenyl)-, (1Z)- 在 lithium tri(t-butoxy)aluminum hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以79%的产率得到(E)-N-(2-chloro-2,2-difluoroethylidene)-4-methoxyaniline
  参考文献：
  名称：

  Facile Preparation of Polyfluoroalkylated Aldimines from Polyfluoroalkanoic Acids

  摘要：

  通过用 LTBA（三叔丁氧基氢化铝锂）还原多氟烷基亚胺酰氯，制备了多氟烷基醛亚胺。

  DOI：

  10.1055/s-2007-966055

文献信息

• The asymmetric synthesis of CF3- or –CF2-substituted tetrahydroquinolines by employing a chiral phosphoric acid as catalyst
  作者：Jin-Hong Lin、Guoqiang Zong、Ruo-Bing Du、Ji-Chang Xiao、Shubin Liu

  DOI：10.1039/c2cc18064b

  日期：——

  CF3- or –CF2-containing tetrahydroquinolines have been asymmetrically synthesized from the reaction of fluorinated N-arylimines with benzyl N-vinylcarbamate in the presence of a chiral phosphoric acid.

  含CF3或CF2的四氢喹啉已通过氟化的N-芳基亚胺与苄基N-乙烯基氨基甲酸酯在手性磷酸的存在下进行不对称合成。
• Asymmetric aza-Henry reaction of fluoromethylated imines catalyzed by cinchona-derived bifunctional thiourea
  作者：Peng Li、Dong-Wei Sun、Min Jiang、Jin-Tao Liu

  DOI：10.1016/j.tet.2018.12.055

  日期：2019.2

  The asymmetric aza-Henry reaction of fluoromethyl imines derived from 4-methoxyaniline with nitromethane was achieved under mild conditions using cinchona-derived bifunctional thiourea as catalyst. A series of chiral fluoromethylated β-nitroamines were synthesized and their transformation to optically pure 4-fluoromethyl-2-imidazolidones was illustrated.

  使用金鸡纳衍生的双官能硫脲作为催化剂，在温和条件下实现了4-甲氧基苯胺衍生的氟甲基亚胺与硝基甲烷的不对称氮杂-亨利反应。合成了一系列手性氟甲基化的β-硝基胺，并说明了它们向光学纯的4-氟甲基-2-咪唑啉酮的转化。
• Highly Enantioselective Synthesis of Fluorinated γ-Amino Alcohols through Proline-Catalyzed Cross-Mannich Reaction
  作者：Santos Fustero、Diego Jiménez、Juan F. Sanz-Cervera、María Sánchez-Roselló、Elisabet Esteban、Antonio Simón-Fuentes

  DOI：10.1021/ol050791f

  日期：2005.8.1

  A new, simple route for the synthesis of fluorinated beta-alkyl gamma-amino alcohols in optically pure form in only two steps and featuring proline catalysis from inexpensive and readily available starting materials is described. The applied strategy allows for the introduction of diversity into both the beta-fluoroalkyl and alpha-alkyl groups of these compounds. [reaction: see text]

  描述了仅两个步骤就以光学纯净形式合成氟化β-烷基γ-氨基醇的新的简单路线，其特征在于从廉价且容易获得的起始原料进行脯氨酸催化。所应用的策略允许将多样性引入到这些化合物的β-氟代烷基和α-烷基中。[反应：看文字]
• Synthesis of fluorinated allylic amines: Reaction of 2-(trimethylsilyl)ethyl sulfones and sulfoxides with fluorinated imines
  作者：Santos Fustero、Sonia Flores、Ana C. Cuñat、Diego Jiménez、Carlos del Pozo、Jorge Bueno、Juan F. Sanz-Cervera

  DOI：10.1016/j.jfluchem.2007.05.006

  日期：2007.10

  reaction of 2-(trimethylsilyl)ethyl sulfones and sulfoxides (as vinyl anion equivalents) with imines and imino esters has been described. The process includes a TBAF-mediated fragmentation of 2-(trimethylsilyl)ethyl sulfones to afford the desired allylic amines. When the reaction is performed with the corresponding sulfoxides, the fragmentation takes place under the addition conditions, affording the final

  已经描述了通过2-（三甲基甲硅烷基）乙基砜和亚砜（作为乙烯基阴离子当量）与亚胺和亚氨基酯反应的氟化烯丙基胺的新合​​成。该方法包括TBAF介导的2-（三甲基甲硅烷基）乙基砜的片段化，以提供所需的烯丙基胺。当用相应的亚砜进行反应时，在加成条件下发生裂解，一步一步得到最终产物。
• Diastereoselective Synthesis of the Nonracemic Methyl <i>syn</i>-(3-Fluoroalkyl)isoserinates
  作者：Ahmed Abouabdellah、Jean-Pierre Bégué、Danièle Bonnet-Delpon、Truong Thi Thanh Nga

  DOI：10.1021/jo971381a

  日期：1997.12.1

  Cycloaddition of the (fluoroalkyl)imines 7a-c with the ketene formed in situ from (benzyloxy)acetyl chloride and triethylamine provided stereoselectively cis-(fluoroalkyl)azetidinones 5a-c in moderate yields. The corresponding N-Boc-isoserinates 11a-c and protected synthons 12a-c have been prepared from these azetidinones 5a-c. Cycloaddition of the chiral imine 18 (R-F = CF3) with the same ketene led to the diastereoisomeric azetidinones 19 and 20 with a poor diastereoisomeric excess (10-20%). However, the two diastereoisomers could be easily separated by crystallization and provided enantiomerically pure N-Boc-isoserinates 23 (R,R) and 23 (S,S) after ring opening and debenzylation.