2-deuterio-3-(hydroxymethyl)quinoline | 101330-12-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-deuterio-3-(hydroxymethyl)quinoline
• 英文别名: 3-Quinoline-2-d-methanol；(2-deuterioquinolin-3-yl)methanol
• CAS: 101330-12-5
• 化学式: C₁₀H₉NO
• 分子量: 160.18
• InChiKey: FLGKQMOTLCGOQH-RAMDWTOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-iodoquinoline-3-carbaldehyde 在 甲醇 、 sodium hydroxide 、 sodium tetrahydroborate 、 正丁基锂 、 氘代甲醇-d 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 18.25h， 生成 2-deuterio-3-(hydroxymethyl)quinoline
  参考文献：
  名称：

  Is halogen-lithium exchange intramolecularly competitive with removal of an acidic hydrogen? Reinvestigation of a recent claim

  摘要：

  A careful reinvestigation of a recent report in which the iodine-lithium exchanges of 2-iodo-3-(deuterioxymethyl)quinoline (1) and 2-iodo-3-(hydroxymethyl)quinoline (4) are interpreted to have occurred prior to abstraction of the alcoholic hydrogen has been carried out. Accurate analyses of the reaction products by FI mass spectrometry give results that are different from those recently reported and are consistent with a mechanism in which removal of the acidic hydrogen takes place prior to iodine-lithium exchange on a molecular scale. The interpretation that suggested the opposite sequence was based on deuterium incorporation values that appear to be inaccurate due to the limitations of the H-1 NMR methods used.

  DOI：

  10.1021/ja00021a026

文献信息

• Narasimhan; Aidhen; Sunder, Journal of the Indian Chemical Society, 1989, vol. 66, # 8-10, p. 703 - 709
  作者：Narasimhan、Aidhen、Sunder

  DOI：——

  日期：——
• NARASIMHAN, NURANI S.;SUNDER, NURANI M.;AMMANAMANCHI, RADHAKRISHNA;BONDE,+, J. AMER. CHEM. SOC., 112,(1990) N1, C. 4431-4435
  作者：NARASIMHAN, NURANI S.、SUNDER, NURANI M.、AMMANAMANCHI, RADHAKRISHNA、BONDE,+

  DOI：——

  日期：——
• NARASIMHAM, N. S.;AMMANAMANCHI, RADHAKRISHNA, J. CHEM. SOC. CHEM. COMMUN., 1985, N 20, 1368-1369
  作者：NARASIMHAM, N. S.、AMMANAMANCHI, RADHAKRISHNA

  DOI：——

  日期：——