1-乙酰基-1H-呋喃并[3,4:4,5]苯并[1,2-d] 咪唑-5,7-二酮 | 108451-45-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 1-乙酰基-1H-呋喃并[3,4:4,5]苯并[1,2-d] 咪唑-5,7-二酮
• 中文别名: 1-乙酰基-1H-呋喃并[3,4:4,5]苯并[1,2-d]咪唑-5,7-二酮
• 英文名称: 1-acetylbenzimidazole-5,6-dicarboxylic anhydride
• 英文别名: 1-Acetyl-1H-furo[3,4-f]benzimidazole-5,7-dione；1-acetylfuro[3,4-f]benzimidazole-5,7-dione
• CAS: 108451-45-2
• 化学式: C₁₁H₆N₂O₄
• 分子量: 230.18
• InChiKey: SQTLPYOAMHSROZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  78.3
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  1-乙酰基-1H-呋喃并[3,4:4,5]苯并[1,2-d] 咪唑-5,7-二酮 在 吡啶 、 氢氧化钾 、 tetraphosphorus decasulfide 、 叠氮基三甲基硅烷 、 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 50.0h， 生成 8-methylthio-3-(2'-deoxy-3',5'-di-O-toluoyl-α-D-ribofuranosyl)imidazo[4,5-g]quinazoline
  参考文献：
  名称：

  Toward a New Genetic System with Expanded Dimensions:  Size-Expanded Analogues of Deoxyadenosine and Thymidine

  摘要：

  We describe the design, preparation, and properties of two key building blocks of a size-expanded genetic system. Nucleoside analogues of the natural nucleosides dA and dT are reported in which the fusion of a benzo ring increases their size by ca. 2.4 Angstrom. The expanded dA analogue (dxA), having a tricyclic base, was first reported by Leonard nearly three decades ago. We describe a shortened and more efficient approach to this compound. The expanded dT analogue (dxT), a methylquinazolinedione C-glycoside, was previously unknown; we describe its preparation in eight steps from 5-methylanthranilic acid. The key glycoside bond formation employed Pd-mediated coupling of an aryl iodide precursor with a dihydrofuran derivative of deoxyribose. Both nucleosides are shown to be efficient fluorophores, emitting light in the blue-violet range. The base-protected phosphoramidite derivatives were prepared, and short oligonucleotides containing them were characterized. The two size-expanded nuclecisides are key components of a new four-base genetic system designed to form helical paired structures having a diameter greater than that of natural DNA. Elements of the design of this expanded genetic molecule, termed xDNA, are discussed, including the possibility of up to eight base pairs of information storage capability.

  DOI：

  10.1021/ja038384r
• 作为产物：
  描述：

  5,6-二甲基苯并咪唑 在 potassium permanganate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 3.0h， 生成 1-乙酰基-1H-呋喃并[3,4:4,5]苯并[1,2-d] 咪唑-5,7-二酮
  参考文献：
  名称：

  Convenient synthesis of linear benzopurines through a common intermediate

  摘要：

  DOI：

  10.1021/jo00389a055

文献信息

• Convenient synthesis of linear benzopurines through a common intermediate
  作者：Nelson J. Leonard、Franciszek Kazmierczak、Andrzej Z. Rykowski

  DOI：10.1021/jo00389a055

  日期：1987.6
• LEONARD N. J.; KAZMIERCZAK F.; RYKOWSKI A., J. ORG. CHEM., 52,(1987) N 13, 2933-2935
  作者：LEONARD N. J.、 KAZMIERCZAK F.、 RYKOWSKI A.

  DOI：——

  日期：——
• Toward a New Genetic System with Expanded Dimensions:  Size-Expanded Analogues of Deoxyadenosine and Thymidine
  作者：Haibo Liu、Jianmin Gao、Lystranne Maynard、Y. David Saito、Eric T. Kool

  DOI：10.1021/ja038384r

  日期：2004.2.1

  We describe the design, preparation, and properties of two key building blocks of a size-expanded genetic system. Nucleoside analogues of the natural nucleosides dA and dT are reported in which the fusion of a benzo ring increases their size by ca. 2.4 Angstrom. The expanded dA analogue (dxA), having a tricyclic base, was first reported by Leonard nearly three decades ago. We describe a shortened and more efficient approach to this compound. The expanded dT analogue (dxT), a methylquinazolinedione C-glycoside, was previously unknown; we describe its preparation in eight steps from 5-methylanthranilic acid. The key glycoside bond formation employed Pd-mediated coupling of an aryl iodide precursor with a dihydrofuran derivative of deoxyribose. Both nucleosides are shown to be efficient fluorophores, emitting light in the blue-violet range. The base-protected phosphoramidite derivatives were prepared, and short oligonucleotides containing them were characterized. The two size-expanded nuclecisides are key components of a new four-base genetic system designed to form helical paired structures having a diameter greater than that of natural DNA. Elements of the design of this expanded genetic molecule, termed xDNA, are discussed, including the possibility of up to eight base pairs of information storage capability.