1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]indole-3-carbaldehyde | 460355-03-7

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]indole-3-carbaldehyde
• CAS: 460355-03-7
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: BCLKHJKHTJFDFR-BFHYXJOUSA-N

物化性质

• 沸点：
  554.1±50.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  71.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]indole-3-carbaldehyde 在 四氮唑 、 4-二甲氨基吡啶 作用下， 以 吡啶 、 乙腈 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  A facile incorporation of the aldehyde function into DNA: 3-formylindole nucleoside as an aldehyde-containing universal nucleoside

  摘要：

  The first facile incorporation of an aldehyde function into DNA without any protection/deprotection of the aldehyde was achieved by the use of 3-formylindole 2'-deoxynucleoside (1). This building block is very easily prepared and efficiently incorporated into oligonucleotides. In addition. 1 acted as a universal nucleoside in duplex. The post-synthetic modification of oligonucleotides bearing 1 with functionalized molecules was also effective. (C) 3003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(02)00888-2
• 作为产物：
  描述：

  1-[(2R,4S,5R)-4-(4-methylphenoxy)-5-[(4-methylphenoxy)methyl]oxolan-2-yl]indole-3-carbaldehyde 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.5h， 以90%的产率得到1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]indole-3-carbaldehyde
  参考文献：
  名称：

  A facile incorporation of the aldehyde function into DNA: 3-formylindole nucleoside as an aldehyde-containing universal nucleoside

  摘要：

  The first facile incorporation of an aldehyde function into DNA without any protection/deprotection of the aldehyde was achieved by the use of 3-formylindole 2'-deoxynucleoside (1). This building block is very easily prepared and efficiently incorporated into oligonucleotides. In addition. 1 acted as a universal nucleoside in duplex. The post-synthetic modification of oligonucleotides bearing 1 with functionalized molecules was also effective. (C) 3003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(02)00888-2