4-methoxybenzyl trifluoroacetimidate | 212051-17-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-methoxybenzyl trifluoroacetimidate
• 英文别名: Ethanimidic acid, 2,2,2-trifluoro-, (4-methoxyphenyl)methyl ester；(4-methoxyphenyl)methyl 2,2,2-trifluoroethanimidate
• CAS: 212051-17-7
• 化学式: C₁₀H₁₀F₃NO₂
• 分子量: 233.19
• InChiKey: JVYROYVBWZNSOY-UHFFFAOYSA-N

物化性质

• 沸点：
  217.8±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  42.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-methoxybenzyl trifluoroacetimidate 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 132.0h， 生成 (-)-1-[3-(4-methoxybenzyloxy)-1-penten-4-yloxycarbonyl]prop-2-yl 5-hydroxy-4-[(2-methoxyethoxy)methoxy]-2-hexenoate
  参考文献：
  名称：

  基于闭环复分解的全合成大分子化合物a和B的新策略。

  摘要：

  [反应：见正文]描述了使用闭环复分解（RCM）作为大环化步骤的新的大环内酯A和B的全合成。RCM的底物可以由容易获得的手性材料，（S）-（+）-3-羟基丁酸甲酯和（S）-（-）-乳酸甲酯合成。RCM在Grubbs的Ru-络合物存在下进行，为这些天然产物提供了一条新的有效合成途径。

  DOI：

  10.1021/ol0350689
• 作为产物：
  描述：

  三氟乙腈 、 4-甲氧基苄醇 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 10.25h， 以200 mg的产率得到4-methoxybenzyl trifluoroacetimidate
  参考文献：
  名称：

  Activated dimethyl sulfoxide dehydration of amide and its application to one-pot preparation of benzyl-type perfluoroimidates

  摘要：

  Various types of primary amides were treated under an activated dimethyl sulfoxide (DMSO) species, (COCl)(2)-DMSO and Et3N, as a dehydrating agent to obtain nitriles in excellent yield. This dehydration system was extended to a one-pot preparation of perfluoroimidates via volatile perfluoronitriles from perfluoroamides. Fifteen benzyl-type perfluoroimidates can be prepared in 70-90% yield as more stable imidates than the trichloro analogue. MPM- and DMPM-perfluoroimidates can be used to protect alcohols in place of the trichloroacetimidate with excellent chemical properties and in comparable yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00304-6

文献信息

• Insecticidal Benzenedicarboxamide Derivative
  申请人：Wada Katsuaki

  公开号：US20110184188A1

  公开（公告）日：2011-07-28

  The present invention relates to a novel benzenedicarboxamide derivative and the use thereof as an insecticide having the formula (I) wherein the chemical groups W 1 to W 9 , and R 1 to R 3 are as defined here-in.

  本发明涉及一种新型苯二甲酰胺衍生物及其作为杀虫剂的用途，其化学式为(I)，其中化学基团W1至W9，以及R1至R3如本文所定义。
• Synthesis of the C1 – C16 fragment of bryostatin for incorporation into 20,20-fluorinated analogues
  作者：Paul R. Mears、Eric J. Thomas

  DOI：10.1016/j.tet.2020.131743

  日期：2021.1

  The stereoselective synthesis of a carboxylic acid ester corresponding to the C1–C16 fragment of bryostatin, with 4-methoxybenzyl (PMB) protection for the 7-hydroxyl group, is reported. The key steps included a Horner-Wadsworth-Emmons reaction between (5R)-3-[(E)-2-tri-isopropylsilyloxyethylidene]-6-(4-methoxybenzyloxy)-5-triethylsilyloxyhexanal and dimethyl (4S,6R,8S)-10-hydroxy-6,8-di-O-isopropy

  据报道，立体选择性合成了与抑霉菌素C1-C16片段相对应的羧酸酯，其中4-羟基甲氧基苄基（PMB）保护7-羟基。关键步骤包括（5 R）-3-[（E）-2-三异丙基甲硅烷氧基乙叉基] -6-（4-甲氧基苄氧基）-5-三乙基甲硅烷氧基己醛与二甲基（4 S，6 R之间的Horner-Wadsworth-Emmons反应，8 S）-10-羟基-6,8-二-O-异亚丙基-4-（4-甲氧基苄氧基）-3,3-二甲基-2-氧杂癸-1-基膦酸酯，得到相应的（E）-烯烃，然后选择性裂解三乙基甲硅烷基醚并环化，得到所需的2,6-顺式-二取代的4-[（Z）-三异丙基甲硅烷氧基乙氧基]四氢吡喃。伯醇的氧化得到相应的羧酸，将其转化为所需的烯丙基酯。
• Preparation and reaction of 4-methoxybenzyl (MPM) and 3,4-dimethoxybenzyl (DMPM) perfluoroimidates
  作者：Noriyuki Nakajima、Miho Saito、Makoto Ubukata

  DOI：10.1016/s0040-4039(98)01121-6

  日期：1998.7

  We have succeeded in one-pot preparation of perfluoroimidates at -78 degrees C by employing the dehydration of perfluoroamide under the "activated" dimethyl sulfoxide (DMSO) species followed by in situ nitrile trapping with alcohols. MPM and DMPM perfluoroimidates can be used to protect alcohols in place of the trichloroacetimidate with excellent chemical properties and in comparable yields. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Formation of Highly Substituted Tetrahydropyranones: Application to the Total Synthesis of Cyanolide A
  作者：Gidget C. Tay、Michael R. Gesinski、Scott D. Rychnovsky

  DOI：10.1021/ol402095g

  日期：2013.9.6

  A new tetrahydropyranone synthesis has been developed that leads to cis-2,6-disubstituted 3,3-dimethyltetrahydropyran-4-one rings by condensation of an aldehyde and a hydroxy silyl enol ether. The reaction works with a variety of aldehydes to produce the tetrahydropyranone products in moderate to high yields. This new method was applied to the enantioselective synthesis of cyanolide A and its aglycone.
• Total Synthesis of Macrosphelides A, B, and E:  First Application of Ring-Closing Metathesis for Macrosphelide Synthesis
  作者：Takanori Kawaguchi、Nobutaka Funamori、Yuji Matsuya、Hideo Nemoto

  DOI：10.1021/jo035435u

  日期：2004.1.1

  A new synthetic route for macrosphelides A, B, and E based on ring-closing metathesis (RCM) was established. The substrates for RCM could be synthesized starting from commercially available chiral materials, methyl (S)-lactate and methyl (S)- or (R)-3-hydroxybutyrate, in good overall yields. In the investigation of the key RCM step, it was found that the steric factor around the reaction site significantly affected the reaction rate of macrocyclization. A detailed account regarding this synthetic study is described herein.