(+/-)-[(Z)-3-benzyl-1-thioxo-1,2,3,4-tetrahydroisoquinolin-4-ylidene]acetic acid | 1021168-08-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (+/-)-[(Z)-3-benzyl-1-thioxo-1,2,3,4-tetrahydroisoquinolin-4-ylidene]acetic acid
• 英文别名: (2Z)-2-(3-benzyl-1-sulfanylidene-2,3-dihydroisoquinolin-4-ylidene)acetic acid
• CAS: 1021168-08-0
• 化学式: C₁₈H₁₅NO₂S
• 分子量: 309.389
• InChiKey: SNLKXIPGWZUVQG-PTNGSMBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-[(Z)-3-benzyl-1-thioxo-1,2,3,4-tetrahydroisoquinolin-4-ylidene]acetic acid 、 异丙醇 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以52%的产率得到isopropyl 2-[3-benzyl-1-chloroisoquinolin-4-y]acetate
  参考文献：
  名称：

  Studies on calpain inhibitors. Synthesis of partially reduced isoquinoline-1-thione derivatives and conversion to functionalized 1-chloroisoquinolines

  摘要：

  Sequential treatment of a (3-substituted-l-thioxo-1,2,3,4-tetrahydroisoquinolin-4-ylidene)acetic acid with thionyl chloride and a nucleophile did not give the expected ester or amide, but a derivative of 2-(3-substituted-1-chloroisoquinolin-4-yl) acetic acid, constituting a simple procedure for the synthesis of functionalized 1-chloroisoquinolines, which can be useful synthetic intermediates. The different reactivity between lactams and thiolactams has been computationally modelled. The activity as calpain inhibitors of both thiolactams and chloroisoquinoline has been measured, finding that some of these compounds are inhibitors in the micromolar range. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.023
• 作为产物：
  描述：

  (+/-)-methyl [(Z)-3-benzyl-1-thioxo-1,2,3,4-tetrahydroisoquinolin-4-ylidene]acetate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到(+/-)-[(Z)-3-benzyl-1-thioxo-1,2,3,4-tetrahydroisoquinolin-4-ylidene]acetic acid
  参考文献：
  名称：

  Studies on calpain inhibitors. Synthesis of partially reduced isoquinoline-1-thione derivatives and conversion to functionalized 1-chloroisoquinolines

  摘要：

  Sequential treatment of a (3-substituted-l-thioxo-1,2,3,4-tetrahydroisoquinolin-4-ylidene)acetic acid with thionyl chloride and a nucleophile did not give the expected ester or amide, but a derivative of 2-(3-substituted-1-chloroisoquinolin-4-yl) acetic acid, constituting a simple procedure for the synthesis of functionalized 1-chloroisoquinolines, which can be useful synthetic intermediates. The different reactivity between lactams and thiolactams has been computationally modelled. The activity as calpain inhibitors of both thiolactams and chloroisoquinoline has been measured, finding that some of these compounds are inhibitors in the micromolar range. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.023