N-<2-Fluor-benzyliden>-2-hydroxy-anilin | 2805-76-7

• 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: N-<2-Fluor-benzyliden>-2-hydroxy-anilin
• 英文别名: GRI 378898；2-(2-fluoro-benzylidenamino)-phenol；2-(2-Fluor-benzylidenamino)-phenol；2-(2-Fluorobenzylideneamino)Phenol；2-[(2-fluorophenyl)methylideneamino]phenol
• CAS: 2805-76-7
• 化学式: C₁₃H₁₀FNO
• mdl: MFCD00768853
• 分子量: 215.227
• InChiKey: SDHKTTFTBJGDQX-UHFFFAOYSA-N

物化性质

• 沸点：
  374.3±27.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-<2-Fluor-benzyliden>-2-hydroxy-anilin 在 palladium diacetate 作用下， 反应 8.0h， 以72.2%的产率得到2-(2-氟苯基)苯并[d]恶唑
  参考文献：
  名称：

  Pd(OAc)2 catalyzed synthesis of 2-aryl- and 2-heteroaryl-benzoxazoles and benzothiazoles in imidazolium ionic liquids (ILs) without additives and with recycling/reuse of the IL

  摘要：

  A facile, high yielding, method for the synthesis of a library of 2-aryl- and 2-heteroaryl-benzoxazoles and benzothiazoles from readily available Schiff bases is reported employing catalytic amounts of Pd(OAc)(2) in imidazolium ionic liquids (bmim)BF4 and (bmim)PF6 without ligands and/or additives. Simple product isolation and recycling/re-use of the IL are additional advantages of this method. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.155
• 作为产物：
  描述：

  2-氟苯甲醛 、 2-氨基苯酚 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-<2-Fluor-benzyliden>-2-hydroxy-anilin
  参考文献：
  名称：

  微波辅助合成取代的二苯并[b，f] [1,4]噻氮平，二苯并[b，f] [1,4]氧杂氮平，苯并噻唑和苯并咪唑

  摘要：

  利用高效的微波辅助一锅法合成（取代的）二苯并[ b，f ] [1,4]噻氮平[1]和二苯并[ b ]，描述了一种具有两个杂原子的7元环的高效合成方法。通过邻氨基硫酚或邻氨基苯酚与邻卤代苯甲醛，邻氟苯乙酮和邻氟二苯甲酮的环缩合，高产率（高达99％）的f ] [1,4]氧杂氮杂[2] 。在没有碱的情况下，邻氨基苯硫酚与邻卤代苯甲醛反应生成苯并噻唑。

  DOI：

  10.1002/jhet.2003

文献信息

• Enantioselective Strecker and Allylation Reactions with Aldimines Catalyzed by Chiral Oxazaborolidinium Ions
  作者：Ki-Tae Kang、Sang Hyun Park、Do Hyun Ryu

  DOI：10.1021/acs.orglett.9b02280

  日期：2019.9.6

  Chiral oxazaborolidinium ion (COBI)-catalyzed enantioselective nucleophilic addition reactions of aldimines using tributyltin cyanide and allyltributylstannane have been developed. Various α-aminonitriles and homoallylic amines were synthesized in high yield (up to 98%) with high to excellent enantioselectivity (up to 99% ee). A rational mechanistic model for the complex of COBI and aldimine is provided

  已经开发了使用氰化三丁基锡和烯丙基三丁基锡烷的手性恶唑硼烷鎓离子（COBI）催化的醛亚胺的对映选择性亲核加成反应。以高产率（高达98％）和高至极好的对映选择性（高达99％ee）合成了各种α-氨基腈和均烯丙基胺。提供了用于COBI和醛亚胺复合物的合理机理模型来解释这些对映选择性反应。
• Preparation of β-Lactams by Mannich-Type Addition of Ethyl(trimethyl­silyl)acetate (ETSA) to N-(2-Hydroxyphenyl)aldimine Sodium Salts
  作者：Sylvain Oudeyer、Vincent Levacher、Vincent Gembus、Thomas Poisson、Francis Marsais

  DOI：10.1055/s-0029-1217729

  日期：2009.9

  The synthesis of highly substituted β-lactams was achieved by addition of air-stable ethyl(trimethylsilyl)acetate derivatives to N-(2-hydroxyphenyl)aldimine sodium salts in a THF-EtCN mixture. This reaction proceeds with moderate to good yields and diastereomeric ratio of up to 78:22. The reactivity of the N-(2-hydroxyphenyl)aldimine can be modified by simply changing the co-solvent from EtCN to MeCN to afford the cyanomethylated addition product.

  通过将空气稳定的乙基（三级甲基硅基）醋酸酯衍生物添加到N-(2-羟基苯基)醛肟钠盐中，成功合成了高度取代的β-内酯。这一反应以中等到良好的产率进行，二聚异构体比率高达78:22。通过简单地将共溶剂从乙腈（EtCN）更改为甲腈（MeCN），可以调节N-(2-羟基苯基)醛肟的反应性，从而获得氰甲基化的加成产物。
• Neighboring phenolic group-activated <i>gem</i>-difluoroallylboration of imines for the catalyst-free synthesis of <i>gem</i>-difluorohomoallylamines
  作者：Xing Yang、Feng Zhang、Yang Zhou、Yi-Yong Huang

  DOI：10.1039/c8ob00541a

  日期：——

  We herein report an unprecedented addition reaction of pinacol gem-difluoroallylborates and imines enabled by a neighboring phenolic group in an N-protecting group under catalyst-free conditions, thus facilitating the construction of a wide range of racemic gem-difluorohomoallylamine derivatives. Based on the control experiments, a plausible transition state via the Zimmerman–Traxler model was proposed

  我们在本文中报道了在无催化剂的条件下，N-保护基团中邻酚酚基的频哪醇宝石-二氟烯丙基硼酸酯和亚胺的空前加成反应，从而促进了广泛的外消旋宝石-二氟同烯丙基胺衍生物的构建。在对照实验的基础上，通过Zimmerman-Traxler模型提出了一个合理的过渡态，以阐明相邻酚基的重要性以及硼酸盐试剂的γ选择性。
• Divergent synthesis of chiral heterocycles via sequencing of enantioselective three-component reactions and one-pot subsequent cyclization reactions
  作者：Min Tang、Dong Xing、Haoxi Huang、Wenhao Hu

  DOI：10.1039/c5cc01979f

  日期：——

  A highly efficient sequencing of enantioselective three-component reactions with a variety of one-pot subsequent cyclization reactions was developed.

  利用一种高效的三组分选择性合成顺序，开发了一系列一锅法后续环化反应。
• Intramolecular Hydrogen Bonding. II. The Determination of Hammett Sigma Constants by Intramolecular Hydrogen Bonding in Schiff's Bases
  作者：A. W. Baker、A. T. Shulgin

  DOI：10.1021/ja01516a001

  日期：1959.4