N-(tert-butoxycarbonyl)-N-(4-chlorobenzyl)-methanesulfonamide | 204857-35-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(tert-butoxycarbonyl)-N-(4-chlorobenzyl)-methanesulfonamide
• 英文别名: N-(tert-butoxycarbonyl)-N-(4-chlorobenzyl)methanesulfonamide；tert-butyl N-(4-chlorobenzyl)-N-(methylsulfonyl)carbamate；tert-butyl N-[(4-chlorophenyl)methyl]-N-methylsulfonylcarbamate
• CAS: 204857-35-2
• 化学式: C₁₃H₁₈ClNO₄S
• 分子量: 319.809
• InChiKey: ZIYXYULDWOAFMX-UHFFFAOYSA-N

物化性质

• 沸点：
  416.1±47.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 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：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-N-(4-chlorobenzyl)-methanesulfonamide 在 palladium on activated charcoal 氢气 、 caesium carbonate 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 55.0h， 生成 6-(1H-imidazol-4-yl)hexane-1-sulfonic acid 4-chlorobenzylamide
  参考文献：
  名称：

  ω-(Imidazol-4-yl)alkane-1-sulfonamides: a new series of potent histamine H3 receptor antagonists

  摘要：

  omega-(1H-imidazol-4-yl)alkane-1-sulfonamides were prepared and found to be potent histamine H-3 receptor antagonists. High receptor affinity and a low difference in the data between the bioassays were achieved with 5-(1H-imidazol-4-yl)pentane-1-sulfonic acid 4-chlorobenzylamide (16). Good in vitro profiles were also obtained for 2-hydroxysulfonamide and vinylsulfonamide analogues. This complements and completes the existing set of imidazole-based sulfonamides and sulfamides. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00295-4
• 作为产物：
  描述：

  对氯苄胺 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(tert-butoxycarbonyl)-N-(4-chlorobenzyl)-methanesulfonamide
  参考文献：
  名称：

  A Convenient Synthesis of N-Alkyl-(E)-1-alkenesulfonamides

  摘要：

  一系列乙烯砜胺3通过N-Boc-甲磺酰胺1和醛2的缩合反应合成。鉴定出O-Boc-2-羟基烷磺酰胺作为中间体，其来源于Boc基团的N-O转移。O-Boc消除后得到乙烯砜胺。

  DOI：

  10.1055/s-1998-1609

文献信息

• Synthesis of Cyclic Sulfonamides through Intramolecular Diels−Alder Reactions
  作者：Ian R. Greig、Matthew J. Tozer、Paul T. Wright

  DOI：10.1021/ol006863e

  日期：2001.2.1

  [figure: see text] Substituted 2,3,3a,4,5,7a-hexahydrobenzo[d]isothiazole 1,1-dioxides and 3,4,4a,5,6,8a-hexahydro-2H-benzo[e][1,2]thiazine 1,1-dioxides, novel cyclic sulfonamides, were synthesized by the thermal Diels-Alder reaction of triene derivatives of buta-1,3-diene-1-sulfonic acid amide. The stereochemical outcome of the reaction was determined by NMR spectroscopy and X-ray crystallographic

  [图：见正文]取代2,3,3a，4,5,7a-六氢苯并[d]异噻唑1,1-二氧化物和3,4,4a，5,6,8a-六氢-2H-苯并[e]新型的环状磺酰胺类[1,2]噻嗪1,1-二氧化物是通过丁-1,3-二烯-1-磺酸酰胺的三烯衍生物的热Diels-Alder反应合成的。反应的立体化学结果通过NMR光谱和X射线晶体学分析确定。该化学物质已用于合成2-（4-氯苄基）-5-（1H-咪唑-4-基）-2,3,3a，4,5,7a-六氢苯并[d]异噻唑1,1-二氧化氮，一种组胺H3受体拮抗剂。
• 1H-4(5)-substituted imidazole derivatives, their preparation and their use as histamine H3 receptor ligands
  申请人：James Black Foundation Limited

  公开号：US06355665B1

  公开（公告）日：2002-03-12

  A compound of the formula wherein R2 is an optionally substituted Cz to Cg alkylene or alkylene chain; R3 is C2 to C15 optionally substituted hydrocarbyl; X is a bond or —NR4—, wherein R4 is hydrogen or non-aromatic C1 to C5 optionally substituted hydrocarbyl, or aryl(C1 to C3)alkyl, or a pharmaceutically acceptable salt thereof. A method of modifing histamine activity in a patient comprising administering to said patient a pharmaceutical composition containing an effective amount of a compound of formula wherein R1 is selected from C1 to C6 alkyl, C1 to C6 alkoxy, C1 to C6 alkylthio, carboxy, carboxy(C1 to C6)alkyl, formyl, C1 to C6 alkylcarbonyl, C1 to C6 alkylcarbonylalkoxy, nitro, trihalomethyl, hydroxy, amino, C1 to C6 alkylcarbonylalkoxy, nitro, trihalomethyl, hydroxy, amino, C1 to C6 alkylamino, di(C1 to C6 alkyl)amino, aryl, C1 to C6 alkylaryl, halo, sulfamoyl and cyano; R2 is optionally substituted C2 to C20 hydrocarbylene, in which one or more hydrogen atoms may be replaced by halogen atoms and up to 6 carbon atoms may be replaced by oxygen or nitrogen atoms, R2 being in the form of an optionally substituted C2 to C8 alkylene or alkenylene chain; R3 is hydrogen or C1 to C15 optionally substituted hydrocarbyl; X is a bond or —NR4—; and a is from 0 to 2, or a pharmaceutically acceptable salt thereof.

  该化合物的化学式中，R2是一个可选取代的Cz到Cg烷基或烷基链；R3是C2到C15可选取代的烃基；X是一个键或-NR4-，其中R4是氢或非芳香C1到C5可选取代的烃基，或芳基(C1到C3)烷基，或其药学上可接受的盐。一种调节组胺在患者体内活性的方法，包括向该患者投予含有一定量该化合物的药物组合物，该化合物的化学式中，R1选自C1到C6烷基，C1到C6烷氧基，C1到C6烷硫基，羧基，羧基(C1到C6)烷基，甲酰基，C1到C6烷基羰基，C1到C6烷基羰基烷氧基，硝基，三卤甲基，羟基，氨基，C1到C6烷基羰基烷氧基，硝基，三卤甲基，羟基，氨基，C1到C6烷基氨基，二(C1到C6烷基)氨基，芳基，C1到C6烷基芳基，卤素，磺酰胺和氰基；R2是可选取代的C2到C20烃基，其中一个或多个氢原子可被卤素原子取代，最多6个碳原子可被氧原子或氮原子取代，R2以可选取代的C2到C8烷基或烯基链的形式存在；R3是氢或C1到C15可选取代的烃基；X是一个键或-NR4-；a为0到2，或其药学上可接受的盐。
• Histamine H3 receptor ligands
  申请人：Kalindjian Sarkis Barret

  公开号：US06878736B1

  公开（公告）日：2005-04-12

  Compounds of formula (I) (and pharmaceutically acceptable salts thereof) are histamine H 3 receptor ligands. A in the formula represents (CH 2 ) m , m being from 1 to 3; B is (CH 2 ) n , n being from 1 to 3; x is from 0 to 2; R 1 is C 1 to C 10 hydrocarbyl, in which up to 2 carbon atoms may be replaced by O, S or N; and up to 2 hydrogen atoms may be replaced by halogen; R 2 is H or C 1 to C 15 hydrocarbyl, in which up to 3 carbon atoms may be replaced by O, S or N, and up to 3 hydrogen atoms may be replaced by halogen; R 3 is absent when —Y—Z—R 2 is attached to W, or is H or C 1 to C 7 hydrocarbyl when —Y—Z—R 2 is not attached to W; W is nitrogen; X is —CH 2 —, —O— or —NR 4 —, R 4 being H or C 1 to C 3 alkyl; Y replaces a hydrogen atom on any of A, B, W and X, and is C 2 to C 10 alkylene, in which one non-terminal carbon atom may be replaced by O; and Z is (II), (III), (IV), (V), (VI), or (VII) wherein R 5 , R 6 and R 7 are independently H or C 1 to C 15 hydrocarbyl, in which up to 3 carbon atoms may be replaced by O or N, and up to 3 hydrogen atoms may be replaced by halogen, and Q is H or methyl, or Q is linked to R 5 or R 7 to form a five-membered ring or Q is linked to R 2 to form a six-membered ring

  公式（I）的化合物（及其药学上可接受的盐）是组胺H3受体配体。 公式中的A代表（CH2）m，其中m为1至3; B为（CH2）n，其中n为1至3; x为0至2; R1为C1至C10烃基，其中最多可有2个碳原子被O，S或N取代; 最多可将2个氢原子替换为卤素; R2为H或C1至C15烃基，其中最多可有3个碳原子被O，S或N取代，最多可将3个氢原子替换为卤素; 当-Y-Z-R2连接到W时，R3不存在，或当-Y-Z-R2未连接到W时，R3为H或C1至C7烃基; W为氮; X为—CH2—，—O—或—NR4—，其中R4为H或C1至C3烷基; Y替换A，B，W和X中的任何一个氢原子，为C2至C10的烷基，其中一个非端碳原子可被O取代; Z为（II），（III），（IV），（V），（VI）或（VII），其中R5，R6和R7独立地为H或C1至C15烃基，其中最多可有3个碳原子被O或N取代，最多可将3个氢原子替换为卤素，Q为H或甲基，或Q与R5或R7连接形成五元环，或Q与R2连接形成六元环。
• HISTAMINE H3 RECEPTOR LIGANDS
  申请人：JAMES BLACK FOUNDATION LIMITED

  公开号：EP1056733B1

  公开（公告）日：2004-01-07
• US6355665B1
  申请人：——

  公开号：US6355665B1

  公开（公告）日：2002-03-12