2-硝基-1-[5-硝基-1-(苯甲基)-1H-咪唑并l-4-基]乙酮 | 69195-97-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-硝基-1-[5-硝基-1-(苯甲基)-1H-咪唑并l-4-基]乙酮
• 英文名称: 2-nitro-1-(1-benzyl-5-nitro-1H-imidazol-4-yl)ethanone
• 英文别名: 1-(1-benzyl-5-nitro-1H-imidazol-4-yl)-2-nitro-ethanone；2-nitro-1-[5-nitro-1-(phenylmethyl)-1H-imidazol-4-yl]ethanone；1-Benzyl-4-nitroacetyl-5-nitroimidazol；1-(1-Benzyl-5-nitro-1H-imidazol-4-yl)-2-nitroethanone；1-(1-benzyl-5-nitroimidazol-4-yl)-2-nitroethanone
• CAS: 69195-97-7
• 化学式: C₁₂H₁₀N₄O₅
• 分子量: 290.235
• InChiKey: NCGPOUCWHOHOER-UHFFFAOYSA-N

物化性质

• 沸点：
  567.2±45.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  2-硝基-1-[5-硝基-1-(苯甲基)-1H-咪唑并l-4-基]乙酮 在 palladium on activated charcoal 吡啶 、 盐酸 、 sodium tetrahydroborate 、 2,2,2-三氟-N,N-二(三甲硅基)乙酰胺 、 氢气 、 sodium methylate 、 四氯化锡 、 tin(ll) chloride 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 25.0h， 生成 3-(2-deoxy-α-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepin-8-ol
  参考文献：
  名称：

  Total synthesis of (8R)-3-(2-deoxy-.beta.-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (pentostatin), the potent inhibitor of adenosine deaminase

  摘要：

  DOI：

  10.1021/jo00139a015
• 作为产物：
  描述：

  1-苄基-4-(二氯甲基)-5-硝基-1H-咪唑 在 sodium chlorite 、 甲酸 、 氨基磺酸 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 20.5h， 生成 2-硝基-1-[5-硝基-1-(苯甲基)-1H-咪唑并l-4-基]乙酮
  参考文献：
  名称：

  Vicarious nucleophilic substitution of 1-benzyl-5-nitroimidazole, application to the synthesis of 6,7-dihydroimidazo[4,5-d][1,3]diazepin-8(3H)-one

  摘要：

  Reaction of 1-benzyl-5-nitroimidazole with carbanion generated from chloroform and potassium tert-butoxide afforded 1-benzyl-4-dichloromethyl-5-nitroimidazole in 72% yield. This vicarious nucleophilic substitution reaction was successfully applied to the synthesis of 6,7-dihydroimidazo[4,5-d][1,3]diazepin-8(3H)-one, an important intermediate in the synthesis of natural and biologically active compounds. (C) 2002 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00053-9

文献信息

• 2-Amino-1-(5-amino-1H-imidazol-4-yl)ethanone and method of preparation
  申请人：Warner-Lambert Company

  公开号：US04117229A1

  公开（公告）日：1978-09-26

  2-Amino-1-(5-amino-1H-imidazol-4-yl)ethanone, 6,7-dihydroimidazo[4,5-d][1,3]diazepin-8(3H)-one and acid-addition salts thereof are disclosed. 2-Amino-1-(5-amino-1H-imidazol-4-yl)ethanone and its acid-addition salts are prepared by catalytically reducing an acid-addition salt of 2-amino-1-[5-amino-1-(protected)-1H-imidazol-4-yl]ethanone. 6,7-Dihydroimidazo[4,5-d][1,3]-diazepin-8(3H)-one and its acid-addition salts are prepared by reacting an acid-addition salt of 2-amino-1-(5-amino-1H-imidazol-4-yl)ethanone with a compound able to contribute a formyl group. The later product may subsequently be converted into (R)-3-(2-deoxy-.beta.-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[ 4,5-d][1,3]diazepin-8-ol. Furanose derivatives of 6,7-dihydroimidazo[4,5-d][1,3]diazepine are also disclosed and their methods of preparation. Lastly, a method for resolving an isomer mixture of 3-(2-deoxy-.beta.-D-erythro-pentafuranosyl)-3,6,7,8-tetrahydroimidazo[4 ,5-d][1,3]diazepin-8-ol compounds is related.

  本文披露了2-氨基-1-(5-氨基-1H-咪唑-4-基)乙酮，6,7-二氢咪唑[4,5-d][1,3]二氮杂环己酮及其酸盐衍生物。2-氨基-1-(5-氨基-1H-咪唑-4-基)乙酮及其酸盐是通过催化还原2-氨基-1-[5-氨基-1-(保护基)-1H-咪唑-4-基]乙酮的酸盐制备的。6,7-二氢咪唑[4,5-d][1,3]-二氮杂环己酮及其酸盐是通过将2-氨基-1-(5-氨基-1H-咪唑-4-基)乙酮的酸盐与能提供甲酰基的化合物反应制备的。后一产品随后可转化为(R)-3-(2-去氧-β-D-赤霉糖-3,6,7,8-四氢咪唑[4,5-d][1,3]二氮杂环己酮-8-醇。还披露了6,7-二氢咪唑[4,5-d][1,3]二氮杂环己烯的呋喃糖衍生物及其制备方法。最后，还涉及一种解决3-(2-去氧-β-D-赤霉糖-3,6,7,8-四氢咪唑[4,5-d][1,3]二氮杂环己酮-8-醇化合物异构体混合物的方法。
• Imidazole compounds, methods for their production and conversion of said
  申请人：Warner-Lambert Company

  公开号：US04195176A1

  公开（公告）日：1980-03-25

  2-Amino-1-(5-amino-1H-imidazol-4-yl)ethanone, 6,7-dihydroimidazo[4,5-d][1,3]diazepin-8(3H)-one and acid-addition salts thereof are disclosed. 2-Amino-1-(5-amino-1H-imidazol-4-yl)ethanone and its acid-addition salts are prepared by catalytically reducing an acid-addition salt of 2-amino-1-[5-amino-1-(protected)-1H-imidazol-4-yl]ethanone. 6,7-Dihydroimidazo[4,5-d][1,3]diazepin-8(3H)-one and its acid-addition salts are prepared by reacting an acid-addition salt of 2-amino-1-(5-amino-1H-imidazol-4-yl)ethanone with a compound able to contribute a formyl group. The later product may subsequently be converted into (R)-3-(2-deoxy-.beta.-D-erythropentofuranosyl)-3,6,7,8-tetrahydroimidazo[4 ,5-d][1,3]diazepin-8-ol. Furanose derivatives of 6,7-dihydroimidazo[4,5-d][1,3]diazepine are also disclosed and their methods of preparation. Lastly, a method for resolving an isomer mixture of 3-(2-deoxy-.beta.-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4 ,5-d][1,3]diazepin-8-ol compounds is related.

  本文介绍了2-氨基-1-(5-氨基-1H-咪唑-4-基)乙酮，6,7-二氢咪唑[4,5-d][1,3]二氮杂环己啶-8(3H)-酮及其酸盐。2-氨基-1-(5-氨基-1H-咪唑-4-基)乙酮及其酸盐是通过催化还原2-氨基-1-[5-氨基-1-(保护基)-1H-咪唑-4-基]乙酮的酸盐制备的。6,7-二氢咪唑[4,5-d][1,3]二氮杂环己啶-8(3H)-酮及其酸盐是通过将2-氨基-1-(5-氨基-1H-咪唑-4-基)乙酮的酸盐与能贡献甲酰基的化合物反应制备的。后者产品随后可转化为(R)-3-(2-去氧-β-D-核糖-喜树糖呋喃基)-3,6,7,8-四氢咪唑[4,5-d][1,3]二氮杂环己啶-8-醇。还介绍了6,7-二氢咪唑[4,5-d][1,3]二氮杂环庚啶的呋喃糖衍生物及其制备方法。最后，介绍了一种解决3-(2-去氧-β-D-赤霉糖-喜树糖呋喃基)-3,6,7,8-四氢咪唑[4,5-d][1,3]二氮杂环己啶-8-醇化合物异构体混合物的方法。
• US4117229A
  申请人：——

  公开号：US4117229A

  公开（公告）日：1978-09-26
• US4195176A
  申请人：——

  公开号：US4195176A

  公开（公告）日：1980-03-25
• Total synthesis of (8R)-3-(2-deoxy-.beta.-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (pentostatin), the potent inhibitor of adenosine deaminase
  作者：Eunice Chan、Sterling R. Putt、H. D. Hollis Showalter、David C. Baker

  DOI：10.1021/jo00139a015

  日期：1982.8