5-methoxy-1H-indole-2-carboxylic acid (2-mercapto-2-methyl-propyl)-amide | 671783-60-1

• 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: 5-methoxy-1H-indole-2-carboxylic acid (2-mercapto-2-methyl-propyl)-amide
• 英文别名: 5-Methoxy-N-(2-methyl-2-sulfanylpropyl)-1H-indole-2-carboxamide；5-methoxy-N-(2-methyl-2-sulfanylpropyl)-1H-indole-2-carboxamide
• CAS: 671783-60-1
• 化学式: C₁₄H₁₈N₂O₂S
• 分子量: 278.375
• InChiKey: YSPCXMQPWAKPAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methoxy-1H-indole-2-carboxylic acid (2-mercapto-2-methyl-propyl)-amide 在 N-氯代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80%的产率得到3-methoxy-6,6-dimethyl-7,8-dihydro-6H,10H-5-thia-8,10-diaza-benzo[a]azulen-9-one
  参考文献：
  名称：

  A Highly Efficient Procedure for 3-Sulfenylation of Indole-2-carboxylates

  摘要：

  A highly efficient one-pot procedure for 3-sulfenylation of 2-carboxyindoles is described. Treatment of thiols with N-chlorosuccinimide at -78 degreesC in CH2Cl2 affords sulfenyl chlorides in situ that readily react with 2-carboxyindoles to give 3-thioindoles in high yields. This new method is milder, produces less waste, and is compatible with a wide range of thiol and indole functionality.

  DOI：

  10.1021/ol049956v
• 作为产物：
  描述：

  5-甲氧基吲哚-2-羧酸 、 2-巯基-2-甲基-1-丙胺 在 N,N'-羰基二咪唑 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以95%的产率得到5-methoxy-1H-indole-2-carboxylic acid (2-mercapto-2-methyl-propyl)-amide
  参考文献：
  名称：

  A Highly Efficient Procedure for 3-Sulfenylation of Indole-2-carboxylates

  摘要：

  A highly efficient one-pot procedure for 3-sulfenylation of 2-carboxyindoles is described. Treatment of thiols with N-chlorosuccinimide at -78 degreesC in CH2Cl2 affords sulfenyl chlorides in situ that readily react with 2-carboxyindoles to give 3-thioindoles in high yields. This new method is milder, produces less waste, and is compatible with a wide range of thiol and indole functionality.

  DOI：

  10.1021/ol049956v

文献信息

• A Highly Efficient Procedure for 3-Sulfenylation of Indole-2-carboxylates
  作者：Kevin M. Schlosser、Alexei P. Krasutsky、Harriet W. Hamilton、Jessica E. Reed、Karen Sexton

  DOI：10.1021/ol049956v

  日期：2004.3.1

  A highly efficient one-pot procedure for 3-sulfenylation of 2-carboxyindoles is described. Treatment of thiols with N-chlorosuccinimide at -78 degreesC in CH2Cl2 affords sulfenyl chlorides in situ that readily react with 2-carboxyindoles to give 3-thioindoles in high yields. This new method is milder, produces less waste, and is compatible with a wide range of thiol and indole functionality.