3-溴-1-(苯基磺酰基)-1H-吡咯-2-甲醛 | 1229516-61-3

• 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: 3-溴-1-(苯基磺酰基)-1H-吡咯-2-甲醛
• 英文名称: N-benzenesulfonyl-3-bromopyrrole-2-carbaldehyde
• 英文别名: 3-bromo-1-(phenylsulfonyl)-1H-pyrrole-2-carbaldehyde；3-bromo-2-formyl-1-phenylsulfonylpyrrole；1-(Benzenesulfonyl)-3-bromopyrrole-2-carbaldehyde
• CAS: 1229516-61-3
• 化学式: C₁₁H₈BrNO₃S
• 分子量: 314.159
• InChiKey: JKNNMQZJGPKZIK-UHFFFAOYSA-N

物化性质

• 熔点：
  69.5-70.5 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  477.7±48.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-溴-1-(苯基磺酰基)-1H-吡咯-2-甲醛 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium diacetate 、 caesium carbonate 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 61.0h， 生成 N-苯磺酸吲哚
  参考文献：
  名称：

  Construction of Carbocyclic Ring of Indoles Using Ruthenium-Catalyzed Ring-Closing Olefin Metathesis

  摘要：

  The selective synthesis of substituted indoles was achieved by the ring-closing olefin metathesis (RCM)/elimination sequence or the RCM/tautomerization sequence of functionalized pyrrole precursors. The RCM/elimination sequence was also applied to double ring closure to yield a substituted carbazole.

  DOI：

  10.1021/ol201510u
• 作为产物：
  描述：

  1-(苯基磺酰基)吡咯 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 三氟甲磺酸 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 28.5h， 生成 3-溴-1-(苯基磺酰基)-1H-吡咯-2-甲醛
  参考文献：
  名称：

  Optional Synthesis of 2- or 5-Substituted 3-Bromopyrroles via Bromine-Lithium Exchange of N-Benzenesulfonyl-2,4-dibromopyrrole

  摘要：

  The regioselective bromine-lithium exchange of N-benzenesulfonyl-2,4-dibromopyrrole (6) with n-BuLi followed by treatment with various electrophiles gave 5-substituted 3-bromopyrroles (5) in excellent yields. In contrast, the sequential treatment of 6 with n-BuLi and diisopropylamine followed by quenching with electrophiles produced regioisomeric 2-substituted 3-bromopyrroles (3) selectively. The latter reaction can be rationalized by the rapid equilibration of the C-5 lithio species (4) to the more stable C-2 lithio species (2) in the presence of diisopropylamine.

  DOI：

  10.3987/com-12-s(n)81

文献信息

• Synthesis of bacteriochlorins bearing diverse β-substituents
  作者：Haoyu Jing、Pengzhi Wang、Boyang Chen、Jianbing Jiang、Pothiappan Vairaprakash、Sijia Liu、Jie Rong、Chih-Yuan Chen、Phattananawee Nalaoh、Jonathan S. Lindsey

  DOI：10.1039/d1nj05852e

  日期：——

  exploited to prepare 6 bacteriochlorins (2 new, 4 known in improved fashion). Each bacteriochlorin contains a gem-dimethyl group in the reduced, pyrroline ring to ensure stability toward adventitious dehydrogenation. These and related synthetic bacteriochlorins have been derivatized to tailor the perimeter of the macrocycle with diverse groups, affording 9 additional new bacteriochlorins and 4 known bacteriochlorins

  合成的细菌绿素是天然细菌叶绿素的类似物，在近红外光谱区域提供吸收，因此对于光化学的基础研究和从太阳能转换到光医学的应用具有重要价值。充分实现这些机会取决于获得合成可延展的菌绿素。在这里，已经开发了两条依赖于二氢二吡啶-乙缩醛或二氢二吡啶-甲醛的自缩合的既定路线来制备 6 种细菌绿素（2 种新的，4 种以改进的方式已知）。每个菌绿素都含有一颗宝石-二甲基在还原的吡咯啉环中，以确保对不定脱氢的稳定性。这些和相关的合成菌绿素已被衍生化，以定制具有不同基团的大环周长，提供 9 种额外的新菌绿素和 4 种已知的菌绿素。通过直接安装和/或衍生，该集合中的附加实体的范围包括烷基、氨基、芳基、溴、乙氧基、氧代、苯乙炔基和吡啶基。菌绿素适用于表面附着、生物共轭、水溶性、振动研究和细化成多发色团阵列。总共描述了 25 种新化合物（11 种菌绿素，14 种前体）的合成。
• Directed Lithiation of <i>N</i>-Benzenesulfonyl-3-bromopyrrole. Electrophile-Controlled Regioselective Functionalization via Dynamic Equilibrium between C-2 and C-5 Lithio Species
  作者：Tsutomu Fukuda、Takeshi Ohta、Ei-ichi Sudo、Masatomo Iwao

  DOI：10.1021/ol100810c

  日期：2010.6.18

  Directed lithiation of N-benzenesulfonyl-3-bromopyrrole (1) with LDA in THF at -78 degrees C generated C-2 lithio species 3 selectively. Reactions of 3 with reactive electrophiles produced the corresponding 2-functionalized pyrroles 4. On the other hand, quenching with less reactive electrophiles generated the corresponding 5-substituted pyrroles 5. The latter unusual functionalization at C-5 could be rationalized by dynamic equilibrium between C-2 and C-5 lithio species,
• Synthesis of 4-Vinylindoles Using Ruthenium-Catalyzed Ring-Closing Enyne Metathesis
  作者：Kazushi Hayashi、Kazuhiro Yoshida、Akira Yanagisawa

  DOI：10.1021/jo400099x

  日期：2013.4.5

  The selective synthesis of substituted 4-vinylindoles by the ring-closing enyne metathesis (RCEM)/dehydration sequence is reported. In contrast with many known methods in which a pyrrole ring is constructed onto a functionalized benzene precursor, this method enables the construction of a benzene ring onto a pyrrole precursor. The RCEM/tautomerization sequence for the synthesis of 7-hydroxy-4-vinylindole is also presented as an application of this method.