1-(甲基磺酰基)吖丁啶 | 13595-45-4

• 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-(甲基磺酰基)吖丁啶
• 中文别名: 1-(甲磺酰)吖丁啶
• 英文名称: 1-methanesulfonyl-azetidine
• 英文别名: azetidine methanesulfonamide；N-Methylsulfonylazetidin；N-Methansulfon-azetidid；N-(Methylsulfonyl)azetidine；1-methylsulfonylazetidine
• CAS: 13595-45-4
• 化学式: C₄H₉NO₂S
• 分子量: 135.187
• InChiKey: RNCROYMBTHIPDN-UHFFFAOYSA-N

物化性质

• 熔点：
  81-82 °C
• 沸点：
  218.8±23.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  8
• 可旋转键数：
  1
• 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：

  苯甲酸甲酯 、 1-(甲基磺酰基)吖丁啶 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 2-(azetidine-1-sulfonyl)-1-phenyl-ethanone
  参考文献：
  名称：

  [EN] PYRROLE-BASED HMG-COA REDUCTASE INHIBITORS
  [FR] INHIBITEURS NOUVEAUX DE L'HMG-COA REDUCTASE A BASE DE PYRROLE

  摘要：

  公开号：

  WO2005014539A3
• 作为产物：
  描述：

  杂氮环丁烷 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以88%的产率得到1-(甲基磺酰基)吖丁啶
  参考文献：
  名称：

  Hepatoselectivity of statins: Design and synthesis of 4-sulfamoyl pyrroles as HMG-CoA reductase inhibitors

  摘要：

  4-Sulfamoyl pyrroles were designed as novel hepatoselective HMG-CoA reductase inhibitors (statins) to reduce myalgia, a statin-induced adverse effect. The compounds were prepared via a [3 + 2] cycloaddition of a Munchnone with a sulfonamide-substituted alkyne. We identified compounds with greater selectivity for hepatocytes compared to L6-myocytes than rosuvastatin and atorvastatin. There was an inverse correlation of myocyte potencies and ClogP values. A number of analogs were effective at reducing cholesterol in acute and chronic in vivo models but they lacked sufficient chronic in vivo activity to warrant further development. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.124

文献信息

• Comparison of the Anionic Ring-Opening Polymerizations of <i>N</i>-(Alkylsulfonyl)azetidines
  作者：Elizabeth A. Rowe、Louis Reisman、Jennifer A. Jefcoat、Paul A. Rupar

  DOI：10.1021/acs.macromol.9b01436

  日期：2019.11.12

  the previously reported polymerization of N-(methanesulfonyl)azetidine (MsAzet). The polymerization kinetics of EsAzet and iPsAzet is of the first order with respect to their monomers and produces p(EsAzet) and p(iPsAzet), which are both soluble in DMF and DMSO. In contrast, the polymerization of tBsAzet proceeds only to low conversion due to precipitation of p(tBsAzet) under identical conditions. At

  N-磺酰基氮杂环丁烷经历阴离子开环聚合（AROP）以形成聚（N-磺酰基氮杂环丁烷），其是有价值的聚亚胺的潜在前体。在这项工作中，烷基磺酰基取代对（N-（乙磺酰基）氮杂环丁烷（EsAzet），N-（2-丙磺酰基）氮杂环丁烷（i PsAzet）和N-（叔丁基磺酰基）氮杂环丁烷（t BsAzet ）的AROP的影响）进行了研究，并与那些先前报道的聚合的ñ - （甲磺酰基）氮杂环丁烷（MsAzet）EsAzet的聚合动力学和我就其单体而言，PsAzet处于第一级，并产生可溶于DMF和DMSO的p（EsAzet）和p（i PsAzet）。相反，由于在相同条件下p（t BsAzet）的沉淀，t BsAzet的聚合仅进行至低转化率。在较低温度（120°C）下，i PsAzet聚合速度最快，而在较高温度（180°C）下，MsAzet速率最快。MsAzet ， EsAzet和i PsAzet的相对聚合速率的
• Hepatoselectivity of statins: Design and synthesis of 4-sulfamoyl pyrroles as HMG-CoA reductase inhibitors
  作者：William K.C. Park、Robert M. Kennedy、Scott D. Larsen、Steve Miller、Bruce D. Roth、Yuntao Song、Bruce A. Steinbaugh、Kevin Sun、Bradley D. Tait、Mark C. Kowala、Bharat K. Trivedi、Bruce Auerbach、Valerie Askew、Lisa Dillon、Jeffrey C. Hanselman、Zhiwu Lin、Gina H. Lu、Andrew Robertson、Catherine Sekerke

  DOI：10.1016/j.bmcl.2007.11.124

  日期：2008.2

  4-Sulfamoyl pyrroles were designed as novel hepatoselective HMG-CoA reductase inhibitors (statins) to reduce myalgia, a statin-induced adverse effect. The compounds were prepared via a [3 + 2] cycloaddition of a Munchnone with a sulfonamide-substituted alkyne. We identified compounds with greater selectivity for hepatocytes compared to L6-myocytes than rosuvastatin and atorvastatin. There was an inverse correlation of myocyte potencies and ClogP values. A number of analogs were effective at reducing cholesterol in acute and chronic in vivo models but they lacked sufficient chronic in vivo activity to warrant further development. (C) 2007 Elsevier Ltd. All rights reserved.
• [EN] PYRROLE-BASED HMG-COA REDUCTASE INHIBITORS<br/>[FR] INHIBITEURS NOUVEAUX DE L'HMG-COA REDUCTASE A BASE DE PYRROLE
  申请人：WARNER LAMBERT CO

  公开号：WO2005014539A3

  公开（公告）日：2005-05-12