2-iodo-N-methyl-1,8-naphthalimide | 1394835-97-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-iodo-N-methyl-1,8-naphthalimide
• CAS: 1394835-97-2
• 化学式: C₁₃H₈INO₂
• 分子量: 337.117
• InChiKey: IPYMIIZAWMMGTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  在 一氯化碘 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 以9%的产率得到2-iodo-N-methyl-1,8-naphthalimide
  参考文献：
  名称：

  An orthomanganation route to 2-substituted derivatives of N-methyl-1,8-naphthalimide

  摘要：

  N-methyl naphthalimide can be readily cyclomanganated at the 2-position, directed by the adjacent amide O atom. Di-cyclomanganation also occurs readily to attach Mn(CO)(4) groups at both 2, 7 positions. An X-ray structure determination of the mono-substituted example confirmed the five-membered metallocyclic ring. Cleavage of the Mn-C bond by HgCl2 or ICl generates 2-substituted HgCl or I derivatives respectively. Reaction of the mono-cyclomanganated N-methyl naphthalimide with phenylacetylene gives an (eta(5)-cyclohexadienyl)Mn(CO)(3) complex where the cyclohexadienyl ring has formed by two PhCCH adding in a formal [2 + 2 + 2] process across the C(1)-C(2) bond of the naphthalimide, breaking the aromaticity of the naphthalene ring as shown by a single crystal structure determination. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.06.035