1-(氯甲基磺酰基)吡咯烷 | 98069-37-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 中文名称: 1-(氯甲基磺酰基)吡咯烷
• 英文名称: Chlormethylsulfonyl-pyrrolidin
• 英文别名: 1-((Chloromethyl)sulfonyl)pyrrolidine；1-(chloromethylsulfonyl)pyrrolidine
• CAS: 98069-37-5
• 化学式: C₅H₁₀ClNO₂S
• 分子量: 183.659
• InChiKey: WNUGGCKSNKHGNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-(氯甲基磺酰基)吡咯烷 在 氢氧化钾 、 sodium hydride 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.25h， 生成 2-phenyl-8-(pyrrolidine-4-sulphonyl)-5,6,7,8-tetrahydroquinoline
  参考文献：
  名称：

  氢/ 1,2,4-三嗪的氢/分子内Diels-Alder反应串联取代亲核取代成功能化的环烯吡啶。

  摘要：

  据报道由1,2,4-三嗪衍生物合成2,3-和3,4-环戊烯吡啶，5,6,7,8-四氢喹啉和5,6,7,8-四氢异喹啉。通过氢的取代基亲核取代，将α-官能化的甲基取代基（例如芳基磺酰基，磺酰胺，磺酸酯）引入三嗪的3-或6-位，随后用在末端位置具有炔属功能的烷基碘进行烷基化，可提供有价值的中间体逆电子需求的分子内Diels-Alder反应。当在较高的温度下加热时，这些三嗪衍生物产生Diels-Alder环加合物，其自发地挤出氮部分后，导致形成多种官能化的环烯基吡啶衍生物。

  DOI：

  10.1248/cpb.50.463
• 作为产物：
  描述：

  四氢吡咯 、 氯甲磺酰氯 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-(氯甲基磺酰基)吡咯烷
  参考文献：
  名称：

  New antifilarial agents. 1. Epoxy sulfonamides and ethynesulfonamides

  摘要：

  Two series of 2-substituted 1,2-epoxyethanesulfonamides 2 and ethynesulfonamides 5 were synthesized and evaluated for their antifilarial activity. The trans epoxides 2T were stereospecifically prepared by a Darzens reaction between aldehydes and halomethanesulfonamides. The cis isomers 2c were obtained from ethynesulfonamides 5 by semihydrogenation followed by KOCl epoxidation. 2-Substituted ethynesulfonamides 5 were synthesized from appropriate trans-ethenesulfonamides by a bromination/dehydrobromination sequence. These products, as well as several synthetic intermediates, were evaluated for antifilarial activity against Molinema dessetae either in vivo in its natural host, the rodent Proechimys oris, or in vitro by a new test using cultures of the infective larvae. Most of the epoxides 2T and acetylenic derivatives 5 bearing a 2-aryl substituent were active in vitro. Among these compounds, four epoxides 2T and one acetylenic derivative 5 showed marked macrofilaricidal activity in vivo without any microfilaricidal activity. The differences between the in vivo and in vitro results may be due, in part, to the low chemical stability of the epoxy sulfonamides 2T. Despite this limitation, the activities observed in this reliable animal model suggest further development and testing of both series 2T and 5 as macrofilaricides.

  DOI：

  10.1021/jm00395a010

文献信息

• Ring Transformation of 3-Halo-1,2,4-triazines with a-Chlorocarbanions: A Novel Route to Pyrazoles with Sulfonyl, Sulfonamido and Sulfonyloxy Groups
  作者：Andrzej Rykowski、Danuta Branowska

  DOI：10.3987/com-96-7554

  日期：——

  A novel route to pyrazoles bearing sulfonyl, sulfonamido and sulfonyloxy groups at C-3 by ring cleavage reaction of 3-halo-6-phenyl-1,2,4-triazines (1a-b) with alpha- halocarbanions (2a-g) is described.
• BRIENE, MARIE-JOSEPHE;VARECH, DANIEL;LECLERCQ, MARTINE;JACQUES, JEAN;BADE+, J. MED. CHEM., 30,(1987) N 12, 2232-2239
  作者：BRIENE, MARIE-JOSEPHE、VARECH, DANIEL、LECLERCQ, MARTINE、JACQUES, JEAN、BADE+

  DOI：——

  日期：——
• ——
  作者：JACQUES J.、 VARECH D.、 BRIENNE M. -J.、 GAYRAL PH.

  DOI：——

  日期：——
• Tandem Vicarious Nucleophilic Substitution of Hydrogen/Intramolecular Diels- Alder Reaction of 1,2,4-Triazines into Functionalized Cycloalkenopyridines.
  作者：Danuta Branowska、Stanislaw Ostrowski、Andrzej Rykowski

  DOI：10.1248/cpb.50.463

  日期：——

  8-tetrahydroquinolines and 5,6,7,8-tetrahydroisoquinolines from 1,2,4-triazine derivatives is reported. Introduction of an alpha-functionalized methyl substituent (e.g. arylsulphonyl, sulphonamide, sulphonic acid ester) into position 3- or 6- of triazines by vicarious nucleophilic substitution of hydrogen and subsequent alkylation with alkyl iodides bearing an acetylenic function in terminal position afforded valuable

  据报道由1,2,4-三嗪衍生物合成2,3-和3,4-环戊烯吡啶，5,6,7,8-四氢喹啉和5,6,7,8-四氢异喹啉。通过氢的取代基亲核取代，将α-官能化的甲基取代基（例如芳基磺酰基，磺酰胺，磺酸酯）引入三嗪的3-或6-位，随后用在末端位置具有炔属功能的烷基碘进行烷基化，可提供有价值的中间体逆电子需求的分子内Diels-Alder反应。当在较高的温度下加热时，这些三嗪衍生物产生Diels-Alder环加合物，其自发地挤出氮部分后，导致形成多种官能化的环烯基吡啶衍生物。
• New antifilarial agents. 1. Epoxy sulfonamides and ethynesulfonamides
  作者：Marie Josephe Brienne、Daniel Varech、Martine Leclercq、Jean Jacques、Nathalie Radembino、Christine Dessalles、Georges Mahuzier、Chantal Gueyouche、Christian Bories

  DOI：10.1021/jm00395a010

  日期：1987.12

  Two series of 2-substituted 1,2-epoxyethanesulfonamides 2 and ethynesulfonamides 5 were synthesized and evaluated for their antifilarial activity. The trans epoxides 2T were stereospecifically prepared by a Darzens reaction between aldehydes and halomethanesulfonamides. The cis isomers 2c were obtained from ethynesulfonamides 5 by semihydrogenation followed by KOCl epoxidation. 2-Substituted ethynesulfonamides 5 were synthesized from appropriate trans-ethenesulfonamides by a bromination/dehydrobromination sequence. These products, as well as several synthetic intermediates, were evaluated for antifilarial activity against Molinema dessetae either in vivo in its natural host, the rodent Proechimys oris, or in vitro by a new test using cultures of the infective larvae. Most of the epoxides 2T and acetylenic derivatives 5 bearing a 2-aryl substituent were active in vitro. Among these compounds, four epoxides 2T and one acetylenic derivative 5 showed marked macrofilaricidal activity in vivo without any microfilaricidal activity. The differences between the in vivo and in vitro results may be due, in part, to the low chemical stability of the epoxy sulfonamides 2T. Despite this limitation, the activities observed in this reliable animal model suggest further development and testing of both series 2T and 5 as macrofilaricides.