(Z)-methyl 2-azido-3-(4-chlorophenyl)acrylate | 102244-86-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-methyl 2-azido-3-(4-chlorophenyl)acrylate
• 英文别名: methyl (Z)-2-azido-3-(4-chlorophenyl)acrylate；4-Chlor-α-azidozimtsaeuremethylester；(Z)-2-azido-3-(4-chlorophenyl)-acrylic acid methyl ester；methyl (Z)-2-azido-3-(4-chlorophenyl)prop-2-enoate
• CAS: 102244-86-0
• 化学式: C₁₀H₈ClN₃O₂
• 分子量: 237.645
• InChiKey: MVNZEYPDIDPWHW-TWGQIWQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-methyl 2-azido-3-(4-chlorophenyl)acrylate 在 Rh₄(3,3'-[1,3-phenylenebis(ethyne-2,1-diyl)]dibenzoicacid(-H))₄(H₂O)₂(dimethylacetamide)₂ 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以96%的产率得到6-氯-2-吲哚羧酸甲酯
  参考文献：
  名称：

  A porous metal–organic cage constructed from dirhodium paddle-wheels: synthesis, structure and catalysis

  摘要：

  一种具有Rh-Rh键的多孔金属-有机笼（MOC-Rh-1）已经制备完成，可作为异质催化剂，并促进偶氮化物的分子内C-H胺化反应。

  DOI：

  10.1039/c5ta05592j
• 作为产物：
  描述：

  2-叠氮基乙酸甲酯 、 4-氯苯甲醛 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.33h， 以51%的产率得到(Z)-methyl 2-azido-3-(4-chlorophenyl)acrylate
  参考文献：
  名称：

  A porous metal–organic cage constructed from dirhodium paddle-wheels: synthesis, structure and catalysis

  摘要：

  一种具有Rh-Rh键的多孔金属-有机笼（MOC-Rh-1）已经制备完成，可作为异质催化剂，并促进偶氮化物的分子内C-H胺化反应。

  DOI：

  10.1039/c5ta05592j

文献信息

• A porous metal–organic cage constructed from dirhodium paddle-wheels: synthesis, structure and catalysis
  作者：Lianfen Chen、Tao Yang、Hao Cui、Tao Cai、Li Zhang、Cheng-Yong Su

  DOI：10.1039/c5ta05592j

  日期：——

  A porous metal–organic cage (MOC-Rh-1) with Rh–Rh bonds has been prepared, which can act as a heterogeneous catalyst and promote the intramolecular C–H amination of azides.

  一种具有Rh-Rh键的多孔金属-有机笼（MOC-Rh-1）已经制备完成，可作为异质催化剂，并促进偶氮化物的分子内C-H胺化反应。
• Iron(II) Triflate as a Catalyst for the Synthesis of Indoles by Intramolecular C−H Amination
  作者：Julien Bonnamour、Carsten Bolm

  DOI：10.1021/ol2004066

  日期：2011.4.15

  A practical iron-catalyzed intramolecular C−H amination reaction and its application in the synthesis of indole derivatives are presented. As a catalyst, commercially available iron(II) triflate is used.

  提出了一种实用的铁催化分子内胺化反应及其在吲哚衍生物合成中的应用。作为催化剂，使用可商购的三氟甲磺酸铁（II）。
• Rapid and easy access to indoles via microwave-assisted Hemetsberger–Knittel synthesis
  作者：Frank Lehmann、Melanie Holm、Stefan Laufer

  DOI：10.1016/j.tetlet.2009.01.129

  日期：2009.4

  Hemetsberger–Knittel indole synthesis can be carried out under microwave activation. The optimum reaction conditions were found by using different solvents and by varying irradiation times and temperature. After 10 min of microwave irradiation, high conversion into the corresponding indole products was achieved without formation of any side products.

  Hemetsberger–Knittel吲哚的合成可以在微波活化下进行。通过使用不同的溶剂以及不同的照射时间和温度可以找到最佳的反应条件。微波辐照10分钟后，实现了向相应吲哚产物的高转化率，而没有形成任何副产物。
• Methyl 2H-Azirine-3-carboxylates as Dienophiles: Synthesis of Methyl 1-Azabicyclo[4.1.0]-hept-3-ene-6-carboxylates
  作者：Pamila Bhullar、Thomas L. Gilchrist、Peter Maddocks

  DOI：10.1055/s-1997-1192

  日期：1997.3

  Methyl 2-aryl-2H-azirine-3-carboxylates are good dienophiles. They react with cyclopentadiene, cyclohexa-1,3-diene and 2,3-dimethylbuta-1,3-diene at or below 50°C to give products of [4+2]-cycloaddition to the carbon-nitrogen double bond. The cycloadditions are endo selective and the dienophiles approach from the less hindered face of the azirines.

  2- 芳基-2H-氮丙啶-3-羧酸甲酯是很好的亲二烯化合物。它们与环戊二烯、环己-1,3-二烯和 2,3-二甲基丁-1,3-二烯在 50°C 或更低的温度下发生反应，生成碳氮双键的 [4+2]- 环加成反应产物。这种环化反应具有内向选择性，亲二烯化合物从氮丙啶的受阻面接近。
• Optimization of Chemical Functionalities of Indole-2-carboxamides To Improve Allosteric Parameters for the Cannabinoid Receptor 1 (CB1)
  作者：Leepakshi Khurana、Hamed I. Ali、Teresa Olszewska、Kwang H. Ahn、Aparna Damaraju、Debra A. Kendall、Dai Lu

  DOI：10.1021/jm5000112

  日期：2014.4.10

  5-Chloro-3-ethyl-N-(4-(piperidin-1-yl)phenethyl)-1H-indole-2-carboxamide (1; ORG27569) is a prototypical allosteric modulator for the cannabinoid type I receptor (CBI). Here, we reveal key structural requirements of indole-2-carboxamides for allosteric modulation of CBI: a critical chain length at the C3-position, an electron withdrawing group at the CS-position, the length of the linker between the amide bond and the phenyl ring B, and the amino substituent on the phenyl ring B. These significantly impact the binding affinity (K-B) and the binding cooperativity (alpha). A potent CB1 allosteric modulator 5-chloro-N-(4(dimethylamino)phenethyl)-3-propyl-1H-indole-2-carboxamide (12d) was identified. It exhibited a K-B of 259.3 nM with a strikingly high binding alpha of 24.5. We also identified 5-chloro-N-(4-(dimethylamino)phenethyl)-3-hexyl-1H-indole-2-carboxamide (120 with a K-B of 89.1 nM, which is among the lowest K-B values obtained for any allosteric modulator of CB1. These positive allosteric modulators of orthosteric agonist binding nonetheless antagonized the agonist-induced G-protein coupling to the CB1 receptor, yet induced beta-arrestin mediated ERK/2 phosphorylation.