N-(tert-butoxycarbonyl)-2-(trimethylstannyl)pyrrole | 172282-33-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N-(tert-butoxycarbonyl)-2-(trimethylstannyl)pyrrole
• 英文别名: N-tert-butoxycarbonyl-2-[tri(n-butyl)stanyl]pyrrole；N-tert-butoxycarbonyl-pyrrolyl stannane；N-Boc-2-(tributylstannyl)pyrrole；(1-(t-butoxycarbonyl)pyrrol-2-yl)tributyltin
• CAS: 172282-33-6
• 化学式: C₂₁H₃₉NO₂Sn
• 分子量: 456.256
• InChiKey: VGFTUFMCGLLLIB-UHFFFAOYSA-N

物化性质

• 沸点：
  450.8±55.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.33
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 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-butoxycarbonyl)-2-(trimethylstannyl)pyrrole 、 1-溴-2-[2-(4-甲基苯基)乙烯基]苯 在 bis-triphenylphosphine-palladium(II) chloride sodium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 72.0h， 以98%的产率得到N-tert-butoxycarbonyl-2-{2-[2-(4-methylphenyl)ethenyl]phenyl}pyrrole
  参考文献：
  名称：

  Photochemistry of stilbenyl-pyrroles: a new approach to indole and isoindole derivatives

  摘要：

  A new 2-{2-[2-(4-methylphenyl)ethenyl]phenyl}pyrrole (11) was prepared and transformed by a photochemical reaction furnishing two cyclised products 4,5-dihydro-4-(p-methylphenyl)benzo[g]indole (12) and 4H-4-(p-methylbenzyl)pyrrolo[2,1-a]isoindole (13), and a reduction product, 2-{2-[2-(4-methylphenyl)ethyl]phenyl}pyrrole (14). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01869-0
• 作为产物：
  描述：

  1-吡咯甲酸叔丁酯 、 三丁基氯化锡 在 2,2,6,6-tetramethylpiperidine lithium 作用下， 以 四氢呋喃 为溶剂， 生成 N-(tert-butoxycarbonyl)-2-(trimethylstannyl)pyrrole
  参考文献：
  名称：

  Synthesis and spectroscopic characterisation of BODIPY® based fluorescent off–on indicators with low affinity for calcium

  摘要：

  两种荧光关闭 Ca2+ 指示剂，基于 APTRA（邻氨基苯酚-N,N,O-三乙酸）作为 Ca2+ 和 BODIPY® 的低亲和力配体 合成了(4,4-二氟-4-bora-3a,4a-二氮杂-s-indacene)作为荧光团。新型 BODIPY® APTRA 化合物在可见光谱中吸收，吸收最大值为 505 nm 至 570 nm，并具有跨越可见光谱的荧光光谱，发射最大值范围为 525 nm 至 625 nm，具体取决于取代基氮原子的α位置。指标显示，随着 Ca2+ 浓度的增加，荧光量子产率大幅增加。在 20 °C 下，在 100 mM KCl 缓冲水溶液（pH 7.20）中，两种 Ca2+ 复合物的基态解离常数 Kd 估计约为 100 µM。

  DOI：

  10.1039/b505969k

文献信息

• 2-heteroaryl-5,11-dihydro-6H-dipyrido\x9b3,2-B:2',3'-E!\x9b1,4!diazepines and
  申请人：Boehringer Ingelheim Pharmaceuticals, Inc.

  公开号：US05837704A1

  公开（公告）日：1998-11-17

  Novel compounds for the treatment of HIV-1 infection. These are 2-heteroary-5,11-dihydro-6H-dipyrido\x9b3,2-b:2',3'-e!\x9b1,4!diazepines of the formula ##STR1## wherein Z is oxygen, sulfur, .dbd.NCN or .dbd.NOR.sup.10 and Ar is a group of the formula I, II, III, IV or V ##STR2##

  治疗HIV-1感染的新化合物。这些是具有以下结构的2-杂环-5,11-二氢-6H-二吡啶\x9b3,2-b:2',3'-e!\x9b1,4!二氮杂环化合物，其中Z为氧、硫、.dbd.NCN或.dbd.NOR.sup.10，Ar为以下结构的基团I、II、III、IV或V。
• Photochemistry of <i>o</i>-Pyrrolylstilbenes and Formation of Spiro-2<i>H</i>-pyrroles and Their Rearrangement to Dihydroindoles
  作者：Nikola Basarić、Željko Marinić、Marija Šindler-Kulyk

  DOI：10.1021/jo061435t

  日期：2006.12.1

  and biradicals 12. Intramolecular cyclization of intermediates 10−12 gives rise to polycyclic compounds spiro-2H-pyrroles 7, pyrroloisoindoles 3, and pyrroloisoquinolines 8. Spiro-2H-pyrroles 7 rearrange on silica gel, giving dihydroindoles 2.

  1,2-二苯乙烯基吡咯1a - 1c的激发态通过两个光化学过程失活：顺式-反式异构化和NH到二苯乙烯双键的氢转移。NH转移导致形成两个醌二甲烷中间体10和11，以及双自由基12。中间体的分子内环化10 - 12产生了多环化合物螺-2 ħ -pyrroles 7，pyrroloisoindoles 3，和pyrroloisoquinolines 8。Spiro-2 H-吡咯7在硅胶上重新排列，得到二氢吲哚2。
• 1,3-Di(2-pyrrolyl)azulene: An Efficient Luminescent Probe for Fluoride
  作者：Husein Salman、Yael Abraham、Shay Tal、Shai Meltzman、Moshe Kapon、Nir Tessler、Shammai Speiser、Yoav Eichen

  DOI：10.1002/ejoc.200500012

  日期：2005.6

  solutions and already appears in interesting commercial applications. In this paper we report on the preparation and host–guest chemistry of 1,3-di(2-pyrrolyl)azulene (5), a new azulene-based selective PET-like chemosensor that turns fluorescent upon binding the fluoride anion. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  基于光诱导能量转移 (PET) 的化学传感是报告溶液中分析物存在的一种非常优雅的方式。该方法已成功应用于检测溶液中的许多阳离子物种，并已出现在有趣的商业应用中。在本文中，我们报告了 1,3-二(2-吡咯基) 芴 (5) 的制备和主客体化学，这是一种新的基于薁的选择性 PET 样化学传感器，在结合氟阴离子时会发出荧光。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Optical and Conformational Studies on Benzobisthiazole Derivatives
  作者：Jun-Gill Kang、Hyun-Joon Kim、Yong-Kwang Jeong、Min-Kook Nah、Changmoon Park、Young Ju Bae、Sang Woo Lee、In Tae Kim

  DOI：10.1021/jp912018h

  日期：2010.3.25

  2,6-Didodecyl-4,8-diphenyl-benzo[1,2-d;4,5-d′]bisthiazole (3) and 2,6-didodecyl-4,8-dipyrrole-2-yl-benzo[1,2-d;4,5-d′]bisthiazole (5) were synthesized, and their optical properties were investigated in solution and in the solid state. Compounds 3 and 5 were excited with the 325 nm He−Cd laser line to produce blue and green luminescence, respectively. The luminescence of 5 (Φ = 14%) was more efficient

  2,6-二十二烷基-4,8-​​二苯基-苯并[1,2- d ; 4,5- d ']双噻唑（3）和2,6-二十二烷基-4,8-​​二吡咯-2-基-苯并[合成了1,2- d ; 4,5- d ']双噻唑（5），并在溶液和固态下研究了它们的光学性质。化合物3和5用325 nm He-Cd激光线激发，分别产生蓝色和绿色发光。5（Φ= 14％）的发光比3（Φ= 5％）的发光更有效。结构和光学性质通过DFT和ZINDO计算进一步确定。平面结构5导致从吡咯部分到苯并双噻唑框架的π→π*电子跃迁，而3的扭曲几何形状导致与苯并噻唑框架内的π→π*跃迁强烈相关的发光。溶剂对5的发光性能的影响概括为分子内和分子间NH···N氢键之间的竞争。
• Novel Non-nucleoside Inhibitors of Human Immunodeficiency Virus Type 1 (HIV-1) Reverse Transcriptase. 4. 2-Substituted Dipyridodiazepinones as Potent Inhibitors of Both Wild-Type and Cysteine-181 HIV-1 Reverse Transcriptase Enzymes
  作者：John R. Proudfoot、Karl D. Hargrave、Suresh R. Kapadia、Usha R. Patel、Karl G. Grozinger、Daniel W. McNeil、Ernest Cullen、Mario Cardozo、Liang Tong

  DOI：10.1021/jm00024a010

  日期：1995.11

  The major cause of viral resistance to the potent human immunodeficiency virus type 1 reverse transcriptase (RT) inhibitor nevirapine is the mutation substituting cysteine for tyrosine-181 in RT (Y181C RT), An evaluation, against Y181C RT, of previously described analogs of nevirapine revealed that the 2-chlorodipyridodiazepinone 16 is an effective inhibitor of this mutant enzyme. The detailed examination of the structure-activity relationship of 2-substituted dipyridodiazepinones presented below shows that combined activity against the wildtype and Y181C enzymes is achieved with aryl substituents at the 2-position of the tricyclic ring system. In addition, the substitution pattern at C-4, N-5, and N-11 of the dipyridodiazepinone ring system optimum for inhibition of both wild-type and Y181C RT is no longer the 4-methyl-11-cyclopropyl substitution preferred against the wild-type enzyme but rather the 5-methyl-11-ethyl (or 11-cyclopropyl) pattern. The more potent 8-substituted dipyridodiazepinones were evaluated against mutant RT enzymes (L100I RT, K103N RT, P236L RT, and E138K RT) that confer resistance to other non-nucleoside RT inhibitors, and compounds 42, 62, and 67, with pyrrolyl, aminophenyl, and aminopyridyl substituents, respectively, at the 2-position, were found to be effective inhibitors of these mutant enzymes also.