(4-甲氧基-苯基)-(2-硝基-苯基)-甲醇 | 100476-07-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (4-甲氧基-苯基)-(2-硝基-苯基)-甲醇
• 英文名称: (4-methoxyphenyl)(2-nitrophenyl)methanol
• 英文别名: (4-Methoxyphenyl)-(2-nitrophenyl)methanol
• CAS: 100476-07-1
• 化学式: C₁₄H₁₃NO₄
• 分子量: 259.262
• InChiKey: KMUDVOWLSJEKOD-UHFFFAOYSA-N

物化性质

• 沸点：
  459.8±40.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-甲氧基-苯基)-(2-硝基-苯基)-甲醇 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 2.17h， 以361 mg的产率得到(2-氨基苯基)(4-甲氧基苯基)甲醇
  参考文献：
  名称：

  Cascade Synthesis of 3-Quinolinecarboxylic Ester via Benzylation/ Propargylation−Cyclization

  摘要：

  Reactions of 2-amino-aryl alcohols with beta-ketoesters catalyzed by a catalytic amout of FeCl3 via tandem benzylation-cyclization produce the corresponding 3-quinolinecarboxylic esters in good to high yields. Extending this methodology to propargylation-cyclization, 2-nitrophenyl proparoyl alcohols with beta-ketoesters catalyzed by FeCl3 and SnCl, also produce the 4-alkyne-3-quitiolinecarboxylic esters. The mechanistic details of this benzylation/proparoylation and cyclization cascade process are also discussed.

  DOI：

  10.1021/jo8017654
• 作为产物：
  描述：

  (4-甲氧基苯基)(2-硝基苯基)甲酮 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 3.5h， 生成 (4-甲氧基-苯基)-(2-硝基-苯基)-甲醇
  参考文献：
  名称：

  Cascade Synthesis of 3-Quinolinecarboxylic Ester via Benzylation/ Propargylation−Cyclization

  摘要：

  Reactions of 2-amino-aryl alcohols with beta-ketoesters catalyzed by a catalytic amout of FeCl3 via tandem benzylation-cyclization produce the corresponding 3-quinolinecarboxylic esters in good to high yields. Extending this methodology to propargylation-cyclization, 2-nitrophenyl proparoyl alcohols with beta-ketoesters catalyzed by FeCl3 and SnCl, also produce the 4-alkyne-3-quitiolinecarboxylic esters. The mechanistic details of this benzylation/proparoylation and cyclization cascade process are also discussed.

  DOI：

  10.1021/jo8017654

文献信息

• The cooperative effect of Lewis pairs in the Friedel–Crafts hydroxyalkylation reaction: a simple and effective route for the synthesis of (±)-carbinoxamine
  作者：Adhikesavan Harikrishnan、Jayakumar Sanjeevi、Chinnasamy Ramaraj Ramanathan

  DOI：10.1039/c4ob02597k

  日期：——

  An efficient C–C bond formation strategy between aromatic/heteroaromatic π-nucleophiles and Lewis acid activated aldehydes is described. This aromatic electrophilic substitution reaction of arenes or heteroarenes is facilitated by Lewis acid AlBr3. Aromatic rings with electron donating substituents are excellent nucleophilic counterparts in this reaction, generating carbinols in excellent yields (61–94%)

  描述了芳族/杂芳族π-亲核试剂与路易斯酸活化醛之间有效的CC键形成策略。路易斯酸AlBr 3促进了芳烃或杂芳烃的芳族亲电取代反应。具有给电子取代基的芳香环在该反应中是极好的亲核对应物，可产生高收率的甲醇（61-94％）。在某些反应性醛和芳香族π-亲核试剂通过反应性碳正离子形成的情况下，也见证了三芳基甲烷的形成。三芳基甲烷的生成可通过以下方式更大程度地减少通过路易斯碱（例如吡啶）与烷氧基铝中间体配位的第二个π-亲核试剂加成的阻滞作用。在存在AlBr 3的情况下，各种脂肪醛也经历了Friedel-Crafts型羟烷基化反应，并以中等收率（41-53％）生成了预期的甲醇。该方案已成功地以单锅法成功用于治疗上重要的组胺H 1拮抗剂（±）-carbinoxamine的合成。
• Cyclopalladated complexes catalyzed addition of arylboronic acids to aldehydes in neat water
  作者：Ajuan Yu、Baoli Cheng、Yangjie Wu、Jingya Li、Kun Wei

  DOI：10.1016/j.tetlet.2008.07.003

  日期：2008.9

  Cyclopalladated ferrocenylimine complexes gave high yields for the addition of arylboronic acids with aldehydes in neat water using a weak acid as additive.

  使用弱酸作为添加剂，在纯净水中将芳基硼酸与醛加成后，环丙二酸二茂铁基亚胺配合物的收率很高。
• Photo-Induced N–N Coupling of <i>o</i>-Nitrobenzyl Alcohols and Indolines To Give <i>N</i>-Aryl-1-amino Indoles
  作者：Yifeng Ou、Tianbao Yang、Niu Tang、Shuang-Feng Yin、Nobuaki Kambe、Renhua Qiu

  DOI：10.1021/acs.orglett.1c02227

  日期：2021.8.20

  N-aryl-1-amino indoles was established by the photoinduced N–N coupling reaction. This protocol is by treatment of o-nitrobenzyl alcohols and indolines in the presence of TEAI and acetic acid with a 24 W ultraviolet (UV) light-emitting diode (LED) (385–405 nm) irradiation. The products bearing an aldehyde group can be further transformed to fluorescent probes based on Rhodamine 6G derivative 11, which shows

  通过光诱导N-N偶联反应建立了一种合成N-芳基-1-氨基吲哚的新方法。该协议是在 TEAI 和乙酸存在下用 24 W 紫外 (UV) 发光二极管 (LED) (385–405 nm) 照射处理邻硝基苄醇和二氢吲哚。带有醛基的产物可以进一步转化为基于罗丹明 6G 衍生物11 的荧光探针，显示出对 Fe 3+的高度特异性和灵敏度。
• Friedel–Crafts hydroxyalkylation through activation of a carbonyl group using AlBr3: an easy access to pyridyl aryl/heteroaryl carbinols
  作者：Adhikesavan Harikrishnan、Jayaraman Selvakumar、Elumalai Gnanamani、Suman Bhattacharya、Chinnasamy Ramaraj Ramanathan

  DOI：10.1039/c2nj40871f

  日期：——

  Aromatic electrophilic substitution of aromatic/electron rich heteroaromatic compounds with AlBr3 activated aldehydes/ketone to afford pyridyl aryl/heteroaryl or diaryl carbinols is described. The strong electron donating group dictates the regiochemical outcome of the product.

  描述了芳香族/电子丰富的杂芳香化合物与AlBr3激活的醛/酮进行芳香电亲核取代反应，以获得吡啶基芳香烃/杂芳烃或二芳基碳醇。强电子给体基团决定了产物的区位化学结果。
• Novel indole-ring formation by thermolysis of 2-(N-acylamino)-benzylphosphonium salts. Effective synthesis of 2-trifluoromethylindoles
  作者：Kazuyuki Miyashita、Katsunori Kondoh、Katsutoshi Tsuchiya、Hideto Miyabe、Takeshi Imanishi

  DOI：10.1039/p19960001261

  日期：——

  Thermolysis of 2-(N-acylamino)benzyl methyl ethers, in the presence of an acid catalyst and triphenylphosphine, or 2-(N-acylamino)benzylphosphonium salts is found to serve as a novel method for indole formation, in particular for the synthesis of 2-trifluoromethylindoles. The reaction of the benzyl methyl ethers is suggested to involve a phosphonium intermediate, which thermally decomposes to the indoles.

  2-(N-酰氨基)苄基甲基醚在酸催化剂和三苯基膦存在下，或在2-(N-酰氨基)苄基膦盐的作用下的热分解被发现是一种新颖的吲哚形成方法，特别用于合成2-三氟甲基吲哚。苄基甲基醚的反应被认为涉及一个膦盐中间体，该中间体通过热分解生成吲哚。