N-tert-butyloxycarbonyl-2-(1'-naphthyl)pyrrole | 215187-31-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-tert-butyloxycarbonyl-2-(1'-naphthyl)pyrrole
• 英文别名: Tert-butyl 2-naphthalen-1-ylpyrrole-1-carboxylate
• CAS: 215187-31-8
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: NNPKULCAOGNTID-UHFFFAOYSA-N

物化性质

• 沸点：
  426.8±43.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-tert-butyloxycarbonyl-2-(1'-naphthyl)pyrrole 在 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 生成 2-萘-1-基-1H-吡咯
  参考文献：
  名称：

  π-延伸对吡咯半硫靛蓝光电开关的影响

  摘要：

  已通过系统地将芳基单元引入母体吡咯半硫靛蓝光开关中，确定了最红移的半硫靛蓝光开关。增加5'-芳基取代基的尺寸对于产生进一步的红移发色团是无效的。报道了具有增加的可调性的第二代3'，5'-二芳基化的光电开关。实验和计算证据表明，4'位置与大部分共轭体系电子隔离。

  DOI：

  10.1016/j.tet.2019.130466
• 作为产物：
  描述：

  1-Boc-吡咯-2-硼酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 以90 %的产率得到N-tert-butyloxycarbonyl-2-(1'-naphthyl)pyrrole
  参考文献：
  名称：

  脱芳香吡咯与偕溴硝基烷的(3+2)反应：合成2,3-二氢吡咯

  摘要：

  1-Boc-吡咯与原位生成的 α-溴亚烷基亚硝基银的脱芳香 1,3-偶极环加成反应生成一系列 3 a ,6 a -二氢-4-Boc-吡咯并[2,3- d ]异恶唑-2-在非常温和的条件下生成氧化物（17-91% 产率）。环加成产物的N-脱氧得到二氢-吡咯并[2,3 -d ]异恶唑，其精加工产生各种官能化的2,3-二氢吡咯和吡咯烷，展示了我们的吡咯脱芳构化新策略的潜在效用。

  DOI：

  10.1039/d4cc01437e

文献信息

• [EN] BIARYL LIGANDS<br/>[FR] LIGANDS BIARYLE
  申请人：UNIV FLORIDA

  公开号：WO2015038872A1

  公开（公告）日：2015-03-19

  Embodiments of the present disclosure provide for biaryl ligands (also referred to herein as "biaryl compound"), biaryl complexes, methods of making biaryl compounds, methods of making single enantiomers of these biaryl compounds, methods of use (e.g., catalysis) and the like.

  本公开的实施例提供了联苯配体（在本文中也称为“联苯化合物”）、联苯配合物的制备方法、制备这些联苯化合物的单对映体的方法、使用方法（例如催化）等。
• Palladium(0)-Catalysed Arylations using Pyrrole and Indole 2-Boronic Acids
  作者：Christopher N. Johnson、Geoffrey Stemp、Neel Anand、Susanna C. Stephen、Timothy Gallagher

  DOI：10.1055/s-1998-1834

  日期：1998.9

  A versatile synthesis of 2-arylpyrroles and 2-arylindoles is described based on the use of either N-(Boc) pyrrole-2-boronic acid or N-(Boc) indole-2-boronic acid as components for Suzuki coupling.

  以 N-(叔丁氧羰基)吡咯-2-硼酸或 N-(叔丁氧羰基)吲哚-2-硼酸作为铃木偶联的组分，介绍了 2-芳基吡咯和 2-芳基吲哚的多功能合成方法。
• Construction of Heterobiaryl Skeletons through Pd-Catalyzed Cross-Coupling of Nitroarenes and Heterocyclic Arylborononate Esters with a Sterically Demanding NHC Ligand
  作者：Wei Chen、Wanzhi Chen、Miaochang Liu、Huayue Wu

  DOI：10.1021/acs.orglett.2c02796

  日期：2022.9.30

  cross-couplings of nitroarenes and heteroarylboronate esters has been developed. A number of heterobiaryl compounds containing pyridine, pyrimidine, quinoline, furan, thiophene, and pyrazole were prepared using [Pd(cinnamyl)Cl]2/2-aryl-5-(2,4,6-triisopropylphenyl)-2,3-imidazolylidene[1,5-a]pyridines as the catalysts in good to excellent yields. The synthetic practicality of this approach is demonstrated through

  已经开发了钯催化的硝基芳烃和杂芳基硼酸酯的 Suzuki-Miyaura 交叉偶联。使用[Pd(肉桂基)Cl] 2 /2-芳基-5-(2,4,6-三异丙基苯基)-2,3-制备了许多含有吡啶、嘧啶、喹啉、呋喃、噻吩和吡唑的杂二芳基化合物咪唑亚基[1,5- a ]吡啶作为催化剂，收率良好。这种方法的合成实用性通过类药物分子的合成得到证明。
• 3,5-Diaryl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) Dyes:  Synthesis, Spectroscopic, Electrochemical, and Structural Properties
  作者：Armin Burghart、Heejin Kim、Mike B. Welch、Lars H. Thoresen、Joe Reibenspies、Kevin Burgess、Fredrik Bergström、Lennart B.-Å. Johansson

  DOI：10.1021/jo990796o

  日期：1999.10.1

  This research was undertaken to obtain new "BODIPY" dyes that fluoresce at relatively long wavelengths. The title compounds 1a-e were prepared via a divergent route involving Suzuki couplings of arylboronic acids to N-tert-butoxycarbonyl-4-bromopyrrole 2, condensation of the products with an acid chloride, and incorporation of the boron difluoride entity. Two alkyl-substituted systems 7a and 7b were also prepared for comparison; the critical difference between structures 1 and 7 is that the former have an aryl group attached to each pyrrole nucleus whereas the latter only have alkyl substituents on that same ring. UV absorption and fluorescence emission data were compared for compounds 1 and 7. Absorption and fluorescence emission maxima for compounds 1 occur at higher wavelengths than for compounds 7, and the Stokes shifts for the aryl-substituted compounds 1 are larger than for the alkyl-substituted compounds 7. Fluorescence quantum yields measured for compounds 1 are less than for compounds 7, and possible reasons for this are outlined. Other physical data for the compounds were also collected. Oxidation and reduction potentials of the systems were obtained from cyclic voltammetry experiments, and a single-crystal X-ray structure determination was performed for the bisnaphthyl-substituted compound 1b.
• Synthesis of 3,5-Diaryl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY^®) Dyes
  作者：Lars H. Thoresen

  DOI：10.1055/s-1998-1924

  日期：1998.11