1-(phenylsulfonyl)-3-(4-methylbenzoyl)pyrrole | 97188-29-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(phenylsulfonyl)-3-(4-methylbenzoyl)pyrrole
• 英文别名: (1-benzenesulfonyl-1H-pyrrol-3-yl)(4-methylphenyl)ketone；1-(1-Benzenesulfonyl-1H-pyrrol-3-yl)-1-p-tolyl-methanone；[1-(benzenesulfonyl)pyrrol-3-yl]-(4-methylphenyl)methanone
• CAS: 97188-29-9
• 化学式: C₁₈H₁₅NO₃S
• 分子量: 325.388
• InChiKey: JXOXUPCGRKCWKC-UHFFFAOYSA-N

物化性质

• 沸点：
  536.6±42.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  1-(phenylsulfonyl)-3-(4-methylbenzoyl)pyrrole 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 生成 1-[1-(1-Benzenesulfonyl-1H-pyrrol-3-yl)-1-p-tolyl-methyl]-1H-imidazole
  参考文献：
  名称：

  1-Arylsulfonyl-3-(α-hydroxybenzyl)-1H-pyrroles, a novel class of anti-HIV-1 reverse transcriptase inhibitors

  摘要：

  Various 1-arylsulfonyl-3-(alpha-hydroxybenzyl)-1H-pyrroles were prepared by Friedel-Crafts reaction of 1-aryisulfonyl-1H-pyrroles with aroylchlorides in the presence of aluminum trichloride, followed by reduction of the ketones to the required carbinols. Title compounds were identified as a novel class of nonnucleoside HIV-1 reverse transcriptase inhibitors characterized by the presence of a diarylcarbinol moiety, a chemical feature that strictly correlates with the anti-HTV-1 activity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00340-5
• 作为产物：
  描述：

  1-(苯基磺酰基)吡咯 在 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.87h， 以100%的产率得到1-(phenylsulfonyl)-3-(4-methylbenzoyl)pyrrole
  参考文献：
  名称：

  WO2006/75638

  摘要：

  公开号：

文献信息

• Pyrrole chemistry XXV: A simplified synthesis of some 3-substituted pyrroles
  作者：Ru Xun Xu、Hugh J. Anderson、Niall J. Gogan、Charles E. Loader、Robert McDonald

  DOI：10.1016/s0040-4039(01)92376-7

  日期：1981.1

  A new synthesis is reported which allows the rapid preparation in good yield of 3-aroyl-, 3-acetyl- and 3-nitro- pyrroles from pyrrole utilizing the 1-benzenesulfonyl group as a blocking group.

  报道了一种新的合成方法，该合成方法允许利用1-苯磺酰基作为封闭基团从吡咯中快速制备3-芳酰基-，3-乙酰基和3-硝基-吡咯。
• A study of the friedel-crafts acylation of 1-benzenesulfonyl-1<i>H</i>-pyrrole in the preparation of 3-aroylpyrroles
  作者：Ioannis Nicolaou、Vassilis J. Demopoulos

  DOI：10.1002/jhet.5570350619

  日期：1998.11

  In this work, we studied the aluminum chloride catalyzed reaction of 1-benzenesulfonyl-1H-pyrrole with a series of eleven aroyl chlorides. The products formed were not isolated, but hydrolyzed to the target 3-aroylpyrroles in overall yields, usually, higher than 50%. However, in the cases with the π electron rich 1-phenyl-1H-pyrrole-3-carbonyl chloride and 1-methyl-1H-indole-3-carbonyl chloride significant

  在这项工作中，我们研究了氯化铝催化的1-苯磺酰基-1 H-吡咯与一系列11种芳酰氯的反应。形成的产物不是分离的，而是水解成目标3-芳基吡咯的总产率，通常高于50％。但是，在富含π电子的1-苯基-1 H-吡咯-3-羰基氯和1-甲基-1 H-吲哚-3-羰基氯的情况下，发生了显着的C-2取代，导致分离出相应的1-苯磺酰基-2-芳酰基吡咯作为主要或唯一产品。从1-三异丙基硅烷基-1 H-吡咯开始合成所需的C-3异构体。
• Synthesis of Three Asymmetric N-Confused Tetraarylporphyrins
  作者：Rajendra Acharya、Liladhar Paudel、Jojo Joseph、Claire E. McCarthy、Venkat R. Dudipala、Jody M. Modarelli、David A. Modarelli

  DOI：10.1021/jo300810n

  日期：2012.7.20

  Two monosubstituted and one tetrasubstituted N-confused porphyrins (1–3) were prepared in ca. 3–5% yields using a [2 + 2] synthesis. The monosubstituted porphyrins have carbomethoxy (1) or nitro (2) substituents on one of the meso-phenyl groups, while the meso-phenyl groups of the third NCP (3) are substituted with nitro, bromo, and methyl groups in an AB2C pattern. The specific regiochemistry of the

  两个单取代的和四取代的一个的N-混淆卟啉（1 - 3）在约制备 使用[2 + 2]合成，产率为3-5％。单取代的卟啉在一个内消旋苯基上具有一个碳甲氧基（1）或一个硝基（2）取代基，而第三个NCP（3）的内消旋苯基在一个AB 2中被硝基，溴和甲基取代C模式。使用1D（1 H和13 D的组合）确定每个卟啉中大环周围芳环的具体区域化学。C）和2D（gHMBC，gHSQC和ROESY）NMR光谱。CH 2 Cl 2中1 – 3的吸收光谱与N混淆的四苯基卟啉（NCTPP）相似，但具有Soret和Q谱带，与NCTPP相比，它们的消光系数向低能量转移。
• Novel heteroaryl derivative
  申请人：Watanabe Ken-ichi

  公开号：US20060194857A1

  公开（公告）日：2006-08-31

  A heteroaryl derivative of the formula (1): (wherein Ring Z is an optionally substituted heteroaryl, R 1 is a carboxyl group or an alkoxycarbonyl group, etc., W 1 and W 2 are an optionally substituted lower alkylene, Ar 1 is an optionally substituted arylene or an optionally substituted heteroarylene, W 3 is a single bond, a lower alkylene, a lower alkenylene, etc., W 4 is a single bond, —NR 10 —, etc., Ar 2 is an optionally substituted aryl or an optionally substituted heteroaryl), or a prodrug thereof, or a pharmaceutically acceptable salt thereof.

  式（1）中，环Z是一种可选的取代杂环基，R1是羧基或烷氧羰基基团等，W1和W2是可选的取代的低碳基链，Ar1是可选的取代芳基或可选的取代杂芳基，W3是单键，低碳基链，低烯基链等，W4是单键，—NR10—等，Ar2是可选的取代芳基或可选的取代杂芳基的杂环基，或其前体药物，或其药物可接受的盐。
• Novel Heteroaryl Derivative
  申请人：Takahashi Yoko

  公开号：US20080167306A1

  公开（公告）日：2008-07-10

  A compound of the following formula (1), or its prodrug or pharmaceutically acceptable salt thereof, being useful as a diabetic medicine or preventive, or blood sugar regulator, or therapeutic agent for hyperlipemia, etc. wherein the ring Z is an optionally substituted heteroaryl, W 4 is a single bond, lower alkylene, etc., Ar 2 is an optionally substituted aryl, etc., W 3 is a single bond, lower alkylene, etc., Ar 1 is an optionally substituted arylene, etc., each of W 1 and W 2 is an optionally substituted lower alkylene, etc., and R 1 is carboxyl, an alkoxycarbonyl.

  下列式子（1）的化合物，或其前药或其药学上可接受的盐，被用作糖尿病药物或预防药物，或血糖调节剂，或高脂血症等治疗剂。其中，环Z是可选取代的杂芳基，W4是单键，低碳链等，Ar2是可选取代的芳基等，W3是单键，低碳链等，Ar1是可选取代的芳烃基等，W1和W2是可选取代的低碳链等，R1是羧基，烷氧羰基等。