lithium salt of 2-tert-butyldimethylsilyl-N,N-dimethylimidazole-1-sulfonamide | 222419-00-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: lithium salt of 2-tert-butyldimethylsilyl-N,N-dimethylimidazole-1-sulfonamide
• 英文别名: 2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl)-imidazol-5-yllithium；2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl)-5-lithioimidazole；5-lithio-2-(tert-butyldimethylsilyl)-N-(dimethylaminosulfonyl)imidazole
• CAS: 222419-00-3
• 化学式: C₁₁H₂₂LiN₃O₂SSi
• 分子量: 295.407
• InChiKey: NWEGZWHLEANNHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.05
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  55.2
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  lithium salt of 2-tert-butyldimethylsilyl-N,N-dimethylimidazole-1-sulfonamide 在 二甲基亚砜 、 三乙胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (2R,3S)-5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-<5-(2'-tert-butyldimethylsilyl)-N-(dimethylaminosulfonyl)imidazolyl>-1,4-pentanedione
  参考文献：
  名称：

  Synthesis and Properties of C-Azalyxonucleosides

  摘要：

  1-beta-(4-Imidazoyl)- and 1-beta-(5-uracilyl)-1,4-dideoxy-1,4-imino-L-lyxitols were synthesized stereoselectively via a sequential procedure by the addition of the corresponding metal salts of heterocycles, Swern oxidation, reductive aminocyclization, and deprotection. Their structures were determined based on X-ray crystallography. From the NMR measurements of their N-acyl derivatives, two rotational isomers were observed. Their bioassay is also described.

  DOI：

  10.1021/jo980492m
• 作为产物：
  描述：

  2-[二甲基(2-甲基-2-丙基)甲硅烷基]-N,N-二甲基-1H-咪唑-1-磺酰胺 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.33h， 生成 lithium salt of 2-tert-butyldimethylsilyl-N,N-dimethylimidazole-1-sulfonamide
  参考文献：
  名称：

  Araki, Lisa; Harusawa, Shinya; Fukuda, Mayuko, Heterocycles, 2001, vol. 55, # 10, p. 1907 - 1917

  摘要：

  DOI：

文献信息

• Synthesis of conformationally locked C-nucleosides having a 2,5-dioxabicyclo[2.2.1]heptane ring system
  作者：Satoshi Obika、Yoshiyuki Hari、Ken-ichiro Morio、Takeshi Imanishi

  DOI：10.1016/s0040-4039(99)01998-x

  日期：2000.1

  Some novel C-nucleosides having a 2,5-dioxabicyclo[2.2.1]heptane ring system were successfully synthesized via the coupling reaction of tetrahydrofurancarbaldehyde 1 with the lithium and the magnesium derivatives of aromatic heterocycles.

  通过四氢呋喃甲醛1与芳族杂环的锂和镁衍生物的偶联反应，成功地合成了具有2,5-二氧杂双环[2.2.1]庚烷环系统的新型C-核苷。
• Effective synthesis of C-nucleosides with 2′,4′-BNA modification
  作者：Yoshiyuki Hari、Satoshi Obika、Minako Sakaki、Ken-ichiro Morio、Yuriko Yamagata、Takeshi Imanishi

  DOI：10.1016/s0040-4020(02)00226-0

  日期：2002.4

  The effective synthesis of some C-nucleosides with 2′-O,4′-C-methylene bridged nucleic acid (2′,4′-BNA) modification was accomplished by using the coupling reaction of a tetrahydrofurancarbaldehyde 1 with the magnesium or lithium derivatives of aromatic heterocycles followed by the Mitsunobu cyclization. Moreover, it was clearly shown by 1H NMR spectra and X-ray crystallography that the sugar conformation

  通过使用四氢呋喃甲醛1与镁或锂衍生物的偶联反应，完成了具有2'- O，4'- C-亚甲基桥连核酸（2'，4'-BNA）修饰的某些C-核苷的有效合成芳香杂环，然后进行Mitsunobu环化。此外，通过1 H NMR谱和X射线晶体学清楚地表明，合成的C-核苷中的糖构象独立于核碱基，被固定为N-形式。
• Synthesis of 4(5)-[5-(Aminomethyl)tetrahydrofuran-2-yl- or 5-(Aminomethyl)-2,5-dihydrofuran-2-yl]imidazoles by Efficient Use of a PhSe Group:  Application to Novel Histamine H₃-Ligands¹
  作者：Shinya Harusawa、Tomonari Imazu、Seiichiroh Takashima、Lisa Araki、Hirofumi Ohishi、Takushi Kurihara、Yasuhiko Sakamoto、Yumiko Yamamoto、Atsushi Yamatodani

  DOI：10.1021/jo9910637

  日期：1999.11.1

  (+)-4(5)-[(2R,5S)-(5-Aminomethyl)tetrahydrofuran-2-yl]imidazole 1 and its C2' epimer (-)-2, which are the 5'-amino derivatives of a novel imidazole C-nucleoside, were synthesized via beta- and alpha-2'-phenylselenenyl nucleosides 15 and 16. The anomers 15 and 16 were provided by a new synthetic method for C-nucleosides via the elimination of PhSeCl and selenocyclization from diol intermediates 12 and 14, starting from L-glutamic acid. Their ent-1 and ent-2 (imifuramine), the latter of which was indicated as a novel type of histamine H-3-agonist confirmed by an in vivo brain microdialysis method, were synthesized by the same methodology from D-glutamic acid. The four isomers (3, 4, ent-3, and ent-4) of a 4(5)-[(5-aminomethyl)-2,5-dihydrofuran-2-yl]imidazole were also synthesized via the oxidative elimination of-the PhSe group of the key intermediates (15, 16, ent-15, and ent-16). In connection with this study, 4(5)-(5-aminomethylfuran-2-yl)-1H-imidazole (5) was also synthesized starting from D-ribose.

  将以下文本翻译成中文： (+)-4(5)-[(2R,5S)-(5-Aminomethyl)tetrahydrofuran-2-yl]imidazole 1 and its C2' epimer (-)-2, which are the 5'-amino derivatives of a novel imidazole C-nucleoside, were synthesized via beta- and alpha-2'-phenylselenenyl nucleosides 15 and 16. The anomers 15 and 16 were provided by a new synthetic method for C-nucleosides via the elimination of PhSeCl and selenocyclization from diol intermediates 12 and 14, starting from L-glutamic acid. Their ent-1 and ent-2 (imifuramine), the latter of which was indicated as a novel type of histamine H-3-agonist confirmed by an in vivo brain microdialysis method, were synthesized by the same methodology from D-glutamic acid. The four isomers (3, 4, ent-3, and ent-4) of a 4(5)-[(5-aminomethyl)-2,5-dihydrofuran-2-yl]imidazole were also synthesized via the oxidative elimination of the PhSe group of the key intermediates (15, 16, ent-15, and ent-16). In connection with this study, 4(5)-(5-aminomethylfuran-2-yl)-1H-imidazole (5) was also synthesized starting from D-ribose. --- (+)-4(5)-[(2R,5S)-(5-氨基甲基)四氢糠基-2-基]咪唑 1 与其 C2' 异构体 (-)-2，作为新型咪唑 C-核苷的 5'-氨基衍生物，通过 beta- 和 alpha-2'-苯基硒基核苷 15 和 16 合成。15 和 16 这种异构体通过一种新型 C-核苷合成方法制得，从 L-谷氨酸出发，通过二醇中间体 12 和 14 消除 PhSeCl 并进行硒环化反应。其 ent-1 和 ent-2（咪吗啡啉），其中后者被确认为一种新型组胺 H-3 �受体激动剂，通过体内脑微透析方法验证，也由此从 D-谷氨酸制得。此外，通过关键中间体（15、16、ent-15 和 ent-16）中 PhSe 基团的氧化消除，合成了 4(5)-[(5-氨基甲基)-2,5-二氢糠基-2-基]咪唑的四种异构体（3、4、ent-3 和 ent-4）。与本研究相关，4(5)-(5-氨基甲基糠基-2-基)-1H-咪唑 (5) 也从 D-核糖开始制得。
• 1,10-(1-H-IMIDAZOL-5-YL)DECANEPHOSPHONIC ACID: A NEW COMPOUND WITH BASIC AND ACIDIC SITES TO FABRICATE PROTON-CONDUCTING SOLID ELECTROLYTES
  作者：Enzo Montoneri、Maria C. Gallazzi、Chiara Bertarelli、Roberto Gobetto、Luca Salassa

  DOI：10.1080/10426500490466355

  日期：2004.9

  temperature to yield the corresponding imidazole diethyl phosphonate, which when refluxed with concentrated HBr yields 1,10-(1-H-imidazol-5-yl)decanephosphonic acid hydrobromide (VI). Compound VI titrated with the required mole equivalents of NaOH yields 1,10-(1-H-imidazol-5-yl)decanephosphonic acid (VII) and 1,10-(1-H-imidazol-5-yl)decane (sodium)phosphonates (VIII). CP-MAS NMR (13C, 31P, and 15N) and IR

  2-(叔丁基二甲基甲硅烷基)-5-(10-溴代癸基)-1-(N,N-二甲基氨磺酰基)-咪唑和 NaPO3 Et2 在室温下反应生成相应的咪唑二乙基膦酸酯，当与浓 HBr 回流时生成 1 ,10-(1-H-咪唑-5-基)癸烷膦酸氢溴酸盐(VI)。用所需摩尔当量的 NaOH 滴定化合物 VI 产生 1,10-(1-H-咪唑-5-基)癸烷膦酸 (VII) 和 1,10-(1-H-咪唑-5-基)癸烷 (钠)膦酸盐(VIII)。CP-MAS NMR（13C、31P 和 15N）和 IR 光谱表明，只有化合物 VII 可能产生聚合结构，其中每个膦酸基团是 H 键合到同一分子的咪唑环和另一个分子的咪唑环上分子。出于这个原因，VII 中的固态质子传导性可能是有利的。
• Stereoselective synthesis of the C-4 linked imidazole nucleosides using modified Mitsunobu reaction
  作者：Shinya Harusawa、Yoshihiko Murai、Hideki Moriyama、Hirofumi Ohishi、Ryuji Yoneda、Takushi Kurihara

  DOI：10.1016/0040-4039(95)00503-5

  日期：1995.5

  stereoselective synthesis of the novel 4-(β-D-ribofuranosyl)imidazole 5 was accomplished in 4 steps and 85% overall yield from protected D-ribose 1. Cyclization of the diol (RS)-3 having an intact imidazole by modified Mitsunobu reaction exclusively afforded benzylated β-ribofuranosylimidazole β-4a, accompanied by α-4a, in a ratio of 26:1. Reductive debenzylation completed the synthesis. 2′-Deoxy derivative

  新的4-（β-D-核呋喃呋喃糖基）咪唑5的高度立体选择性合成从受保护的D-核糖1分四个步骤完成，并且总产率为85％。通过改性将具有完整咪唑的二醇（RS）-3环化Mitsunobu反应仅以26：1的比例提供苄基化的β-核呋喃基呋喃基咪唑β- 4a和α- 4a。还原性脱苄基反应完成了合成。还以相同的方式立体选择性地合成了2'-脱氧衍生物8。