2-(p-Chlor-benzylidenamino)-p-kresol | 20219-08-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(p-Chlor-benzylidenamino)-p-kresol
• 英文别名: 2-[(4-Chlorophenyl)methylideneamino]-4-methylphenol
• CAS: 20219-08-3
• 化学式: C₁₄H₁₂ClNO
• 分子量: 245.708
• InChiKey: SUEXOJATEBGKAO-UHFFFAOYSA-N

物化性质

• 沸点：
  425.9±45.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(p-Chlor-benzylidenamino)-p-kresol 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 2-[(4-chlorophenyl)methyl]amino-4-methylphenol
  参考文献：
  名称：

  Design, Synthesis, and Biological Activity of New N-(Phenylmethyl)-benzoxazol-2-thiones as Macrophage Migration Inhibitory Factor (MIF) Antagonists: Efficacies in Experimental Pulmonary Hypertension

  摘要：

  Macrophage migration inhibitory factor (MIF) is a key pleiotropic mediator and a promising therapeutic target in cancer as well as in several inflammatory and cardiovascular diseases including pulmonary arterial hypertension (PAH). Here, a novel series of N-(phenylmethyl)-benzoxazol-2-thiones 5-32 designed to target the MIF tautomerase active site was synthesized and evaluated for its effects on cell survival. Investigation of structure-activity relationship (SAR) particularly at the 5-position of the benzoxazole core led to the identification of 31 that potently inhibits cell survival in DU-145 prostate cancer cells and pulmonary endothelial cells derived from patients with idiopathic PAH (iPAH-ECs), two cell lines for which survival is MIF-dependent. Molecular docking studies helped to interpret initial SAR related to MIF tautomerase inhibition and propose preferred binding mode for 31 within the MIF tautomerase active site. Interestingly, daily treatment with 31 started 2 weeks after a subcutaneous monocrotaline injection regressed established pulmonary hypertension in rats.

  DOI：

  10.1021/acs.jmedchem.7b01312
• 作为产物：
  描述：

  2-硝基-4-甲苯酚 、 DL-对氯苯甘氨酸 在 potassium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 20.0h， 生成 2-(p-Chlor-benzylidenamino)-p-kresol
  参考文献：
  名称：

  水性介质中苯甘氨酸与2-硝基苯酚的意外脱羧引发的邻羟基控制的氧化还原缩合

  摘要：

  据报道，采用脱羧触发和邻羟基控制的氢转移策略，可以从容易获得的氨基酸和2-硝基酚一锅法合成苯并恶唑。在这种自动氧化还原反应的基础上，可以在水性介质中在无过渡金属的条件下有效构建CN键，以中等至良好的产率获得所需的产物。

  DOI：

  10.1002/adsc.201800586

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。
• Synthesis of 2-arylbenzoxazoles via DDQ promoted oxidative cyclization of phenolic Schiff bases—a solution-phase strategy for library synthesis
  作者：Junbiao Chang、Kang Zhao、Shifeng Pan

  DOI：10.1016/s0040-4039(01)02302-4

  日期：2002.2

  The Schiff base derived from the condensation of o-aminophenol with benzaldehydes was induced to undergo oxidative cyclization in the presence of DDQ. The resulting 2-arylbenzoxazoles were separated from the reduced DDQ byproduct by treatment of reaction mixture with a strongly basic ion-exchange resin. The applicability of this chemistry to spatially separate library synthesis is demonstrated by the

  在DDQ存在下，诱导衍生自邻氨基苯酚与苯甲醛缩合的席夫碱进行氧化环化反应。通过用强碱性离子交换树脂处理反应混合物，从还原的DDQ副产物中分离出所得的2-芳基苯并恶唑。通过制备352个成员的文库，证明了该化学方法在空间上分离文库合成的适用性。
• Design, Synthesis, and Biological Activity of New <i>N</i>-(Phenylmethyl)-benzoxazol-2-thiones as Macrophage Migration Inhibitory Factor (MIF) Antagonists: Efficacies in Experimental Pulmonary Hypertension
  作者：Morane Le Hiress、Bernardin Akagah、Guillaume Bernadat、Ly Tu、Raphaël Thuillet、Alice Huertas、Carole Phan、Elie Fadel、Gérald Simonneau、Marc Humbert、Gaël Jalce、Christophe Guignabert

  DOI：10.1021/acs.jmedchem.7b01312

  日期：2018.4.12

  Macrophage migration inhibitory factor (MIF) is a key pleiotropic mediator and a promising therapeutic target in cancer as well as in several inflammatory and cardiovascular diseases including pulmonary arterial hypertension (PAH). Here, a novel series of N-(phenylmethyl)-benzoxazol-2-thiones 5-32 designed to target the MIF tautomerase active site was synthesized and evaluated for its effects on cell survival. Investigation of structure-activity relationship (SAR) particularly at the 5-position of the benzoxazole core led to the identification of 31 that potently inhibits cell survival in DU-145 prostate cancer cells and pulmonary endothelial cells derived from patients with idiopathic PAH (iPAH-ECs), two cell lines for which survival is MIF-dependent. Molecular docking studies helped to interpret initial SAR related to MIF tautomerase inhibition and propose preferred binding mode for 31 within the MIF tautomerase active site. Interestingly, daily treatment with 31 started 2 weeks after a subcutaneous monocrotaline injection regressed established pulmonary hypertension in rats.
• Unexpected Decarboxylation-Triggered <i>o</i> -Hydroxyl-Controlled Redox Condensation of Phenylglycines with 2-Nitrophenols in Aqueous Media
  作者：Lin Tang、Zhen Yang、Tian Sun、Di Zhang、Xiantao Ma、Weihao Rao、Yuqiang Zhou

  DOI：10.1002/adsc.201800586

  日期：2018.8.17

  o‐hydroxyl‐controlled hydrogen‐transfer strategy for the one‐pot synthesis of benzoxazoles from readily available amino acids and 2‐nitrophenols is reported. On the basis of this autoredox reaction, the C−N bond can be efficiently constructed to afford the desired products in moderate to good yields under transition‐metal‐free conditions in aqueous media.

  据报道，采用脱羧触发和邻羟基控制的氢转移策略，可以从容易获得的氨基酸和2-硝基酚一锅法合成苯并恶唑。在这种自动氧化还原反应的基础上，可以在水性介质中在无过渡金属的条件下有效构建CN键，以中等至良好的产率获得所需的产物。