1-N-丁基-1-甲苯磺酰甲基异丁酯 | 58379-83-2

• 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: 1-N-丁基-1-甲苯磺酰甲基异丁酯
• 英文名称: 1-[(1-isocyanopentyl)sulfonyl]-4-methylbenzene
• 英文别名: 1-n-butyltosylmethylisocyanide；1-(1-isocyanopentane-1-sulfonyl)-4-methylbenzene；1-n-Butyl-1-tosylmethyl isocyanide；1-(1-isocyanopentylsulfonyl)-4-methylbenzene
• CAS: 58379-83-2
• 化学式: C₁₃H₁₇NO₂S
• 分子量: 251.349
• InChiKey: UJVOYIUYZNRPPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  46.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-N-丁基-1-甲苯磺酰甲基异丁酯 在 四丙基高钌酸铵 、 potassium tert-butylate 、 sodium hydride 、 二异丁基氢化铝 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 、 mineral oil 为溶剂， 反应 5.5h， 生成 5-butyl-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde
  参考文献：
  名称：

  Discovery, synthesis, and biological evaluation of novel pyrrole derivatives as highly selective potassium-competitive acid blockers

  摘要：

  To discover a gastric antisecretory agent more potent than existing proton pump inhibitors, novel pyrrole derivatives were synthesized, and their H+, K+-ATPase inhibitory activities and inhibitory action on histamine-stimulated gastric acid secretion in rats were evaluated. Among the compounds synthesized, compound 17a exhibited selective and potent H+, K+-ATPase inhibitory activity through reversible and K+-competitive ionic binding; furthermore, compound 17c exhibited potent inhibitory action on histamine-stimulated gastric acid secretion in rats and Heidenhain pouch dogs. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.014
• 作为产物：
  描述：

  1-碘丁烷 在 sodium hydroxide 、 对甲基苯磺酰甲基异腈 、 四丁基碘化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 16.0h， 以87%的产率得到1-N-丁基-1-甲苯磺酰甲基异丁酯
  参考文献：
  名称：

  [EN] HYDROXYL COMPOUNDS AND COMPOSITIONS FOR CHOLESTEROL MANAGEMENT AND RELATED USES
  [FR] COMPOSES HYDROXYLES ET COMPOSITIONS DE REGULATION DU CHOLESTEROL ET UTILISATIONS ASSOCIEES

  摘要：

  公开号：

  WO2004067489A3

文献信息

• Silver-Catalyzed Isocyanide-Isocyanide [3+2] Cross-Cycloaddition Involving 1,2-Group Migration: Efficient Synthesis of Trisubstituted lmidazoles
  作者：Hongwei Wang、Rapolu Kiran Kumar、Yang Yu、Lin Zhang、Zhaohong Liu、Peiqiu Liao、Xihe Bi

  DOI：10.1002/asia.201601024

  日期：2016.10.20

  molecules. The isocyanide–isocyanide [3+2] cross‐cycloaddition reaction constitutes a straightforward method to access imidazoles starting from the easily available chemicals. So far, only three successive reports are known and all lead to the formation of 1,4‐disubstituted imidazoles. Here, we report the first isocyanide–isocyanide [3+2] cross‐cycloaddition reaction allowing for the formation of 1,4,5‐trisubstituted

  咪唑环是重要的五元芳族杂环，广泛存在于天然产物和合成分子中。异氰酸酯–异氰酸酯[3 + 2]的交叉环加成反应是从易获得的化学品开始获取咪唑的直接方法。到目前为止，只有三份连续的报告是已知的，所有这些都导致形成1,4-二取代的咪唑。在这里，我们报道了第一个异氰酸酯-异氰酸酯[3 + 2]交叉环加成反应，该反应允许在银催化下形成1,4,5-三取代的咪唑。在环化过程中，磺酰基，烷氧基羰基和氨基甲酰基发生了意外的1,2-迁移，这是三取代咪唑形成的原因。
• Substituted indole derivatives
  申请人：Syntex (U.S.A.) Inc.

  公开号：US05380739A1

  公开（公告）日：1995-01-10

  Compounds of the Formula (I), (II), or (III): ##STR1## wherein the variables are as defined in the specification and the pharmaceutically acceptable salts thereof, exhibit useful pharmacological properties, and are particularly useful as angiotensin II antagonists.

  化合物的结构式（I）、（II）或（III）：##STR1##其中变量如规范中所定义，并且其药学上可接受的盐具有有用的药理特性，特别适用作为血管紧张素II拮抗剂。
• Substituted indole antagonists derivatives which are angiotensin II
  申请人：Syntex (U.S.A.) Inc.

  公开号：US05212195A1

  公开（公告）日：1993-05-18

  Compound of the Formula (I), (II), or (III): ##STR1## wherein: R.sup.1 is lower alkyl or 2"-(1H-tetrazol-5-yl)biphenyl-4'-ylmethyl; R.sup.2 is lower alkyl when R.sup.1 is 2"-(1H-tetrazol-5-yl)biphenyl-4'-ylmethyl; or R.sup.2 is 2"-(1H-tetrazol-5-yl)biphenyl-4'-ylmethyl when R.sup.1 is lower alkyl; R.sup.3 is hydrogen or lower alkyl; X is hydrogen, lower alkyl, halogen, --C(O)CF.sub.3, --CO.sub.2 R.sup.4, or --C(O)NR.sup.5 R.sup.6 ; Y is hydrogen, lower alkyl, lower alkoxy, hydroxy, halogen, or --CO.sub.2 R.sup.4 ; Z is hydrogen, lower alkyl, lower alkoxy, or halogen; with the proviso that Y and Z cannot be attached to the nitrogen atom in Formula (II); wherein R.sup.4 is hydrogen or lower alkyl; R.sup.5 is hydrogen or lower alkyl; R.sup.6 is hydrogen or lower alkyl; or R.sup.5 and R.sup.6 taken together with the nitrogen to which they are attached represent a heterocycle; and pharmaceutically acceptable salts thereof, exhibit useful pharmacological properties, and are particularly useful as angiotensin II antagonists.

  化合物的结构（I），（II）或（III）：##STR1##其中：R.sup.1是较低的烷基或2"-(1H-四唑-5-基)联苯-4'-基甲基；当R.sup.1是2"-(1H-四唑-5-基)联苯-4'-基甲基时，R.sup.2是较低的烷基；或者当R.sup.1是较低的烷基时，R.sup.2是2"-(1H-四唑-5-基)联苯-4'-基甲基；R.sup.3是氢或较低的烷基；X是氢，较低的烷基，卤素，-C(O)CF.sub.3，-CO.sub.2R.sup.4，或-C(O)NR.sup.5R.sup.6；Y是氢，较低的烷基，较低的烷氧基，羟基，卤素，或-CO.sub.2R.sup.4；Z是氢，较低的烷基，较低的烷氧基，或卤素；但Y和Z不能连接到式（II）中的氮原子；其中R.sup.4是氢或较低的烷基；R.sup.5是氢或较低的烷基；R.sup.6是氢或较低的烷基；或R.sup.5和R.sup.6与它们连接的氮一起代表一个杂环；以及其药学上可接受的盐，展示出有用的药理特性，特别适用于作为血管紧张素II拮抗剂。
• One-Pot Van Leusen Synthesis of 4,5-Disubstituted Oxazoles in Ionic Liquids
  作者：Xiao-Qi Yu、Bo Wu、Jun Wen、Ji Zhang、Jing Li、Yong-Zhe Xiang

  DOI：10.1055/s-0028-1087547

  日期：2009.2

  An efficient and mild protocol for the preparation of 4,5-disubstituted oxazoles through an improved one-pot van Leusen oxazole synthesis in ionic liquids is described. The oxazole products were prepared from tosylmethyl isocyanide (TosMIC), aliphatic halides and various aldehydes in high yields. The recovered ionic liquids could be reused as solvent for six runs without significant loss of yields.

  本文介绍了在离子液体中通过改进的单锅 van Leusen噁唑合成法制备 4,5-二取代噁唑的高效而温和的方案。以甲苯基甲基异氰酸酯 (TosMIC)、脂肪族卤化物和各种醛为原料，高产率地制备了噁唑产品。回收的离子液体可作为溶剂重复使用六次，且收率无明显下降。
• Heterocyclizations with Tosylmethyl Isocyanide Derivatives. A New Approach to Substituted Azolopyrimidines
  作者：Alejandro Baeza、Javier Mendiola、Carolina Burgos、Julio Alvarez-Builla、Juan J. Vaquero

  DOI：10.1021/jo050029r

  日期：2005.6.1

  An efficient synthesis of substituted azolopyrimidines such as pyrido[3‘,2‘:4,5]pyrrolo[1,2-c]pyrimidines, pyrimido[1,6-a]indoles, benzo[4,5]imidazo-[1,2-c]pyrimidines, an imidazo[1,2-c]pyrimidine, and pyrazolo[1,5-c]pyrimidines is described. The method involves the reaction of N-protected bromomethylazoles and tosylmethyl isocyanide (TosMIC) derivatives in nonanhydrous media. The study of the reaction

  高效合成取代的吡唑并嘧啶，例如吡啶并[3'，2'：4,5]吡咯并[1,2- c ]嘧啶，嘧啶并[1,6- a ]吲哚，苯并[4,5]咪唑并[1]描述了，2- c ]嘧啶，咪唑并[1,2- c ]嘧啶和吡唑并[1,5- c ]嘧啶。该方法涉及在无水介质中N保护的溴甲基唑与甲苯磺酰基甲基异氰化物（TosMIC）衍生物的反应。对反应条件的研究表明，该方法仅在使用苄基三乙基氯化铵作为催化剂的相转移条件下（CH 2 Cl 2 /30％NaOH水溶液）成功。