2-chloromethyl-5-methoxy-1-methyl-1H-indole-3-carboxylic acid methyl ester | 928007-81-2

• 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: 2-chloromethyl-5-methoxy-1-methyl-1H-indole-3-carboxylic acid methyl ester
• CAS: 928007-81-2
• 化学式: C₁₃H₁₄ClNO₃
• 分子量: 267.712
• InChiKey: SVJINYBPORRWDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  40.46
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-chloromethyl-5-methoxy-1-methyl-1H-indole-3-carboxylic acid methyl ester 在 2,6-二甲基吡啶 、 三甲基铝 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 7-methoxy-2-[4-methoxy-3-(2-piperidin-1-ylethoxy)phenyl]-4-methyl-3H-pyrrolo[3,4-b]indol-1-one
  参考文献：
  名称：

  5-HT2C antagonists based on fused heterotricyclic templates: Design, synthesis and biological evaluation

  摘要：

  Design, synthesis and properties of a new tricyclic series of selective 5-HT2C receptor antagonists are reported. Conformational analysis of a 2-phenyl-dihydropyrrolone scaffold suggested that ring fusion, locking coplanarity between the rings of this moiety, might be tolerated by the 5-HT2C receptor. An interesting effect of this is the change of the nature of the carbon-carbon double bond of the lactam ring from vinylic to aromatic. The changes were found to result in a favourable profile at both, receptor and in vivo level. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.034
• 作为产物：
  描述：

  methyl 5-methoxy-1,2-dimethyl-1H-indole-3-carboxylate 在 N-氯代丁二酰亚胺 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 生成 2-chloromethyl-5-methoxy-1-methyl-1H-indole-3-carboxylic acid methyl ester
  参考文献：
  名称：

  5-HT2C antagonists based on fused heterotricyclic templates: Design, synthesis and biological evaluation

  摘要：

  Design, synthesis and properties of a new tricyclic series of selective 5-HT2C receptor antagonists are reported. Conformational analysis of a 2-phenyl-dihydropyrrolone scaffold suggested that ring fusion, locking coplanarity between the rings of this moiety, might be tolerated by the 5-HT2C receptor. An interesting effect of this is the change of the nature of the carbon-carbon double bond of the lactam ring from vinylic to aromatic. The changes were found to result in a favourable profile at both, receptor and in vivo level. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.034