1,3-Dichloro-6-hydroxy-5,6-dihydro-cyclopenta[c]thiophen-4-one | 246232-35-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-Dichloro-6-hydroxy-5,6-dihydro-cyclopenta[c]thiophen-4-one
• 英文别名: 1,3-Dichloro-6-hydroxy-5,6-dihydrocyclopenta[c]thiophen-4-one
• CAS: 246232-35-9
• 化学式: C₇H₄Cl₂O₂S
• 分子量: 223.08
• InChiKey: IPLHVUWWQLHYTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-Dichloro-6-hydroxy-5,6-dihydro-cyclopenta[c]thiophen-4-one 在 chromium(VI) oxide 、 硫酸 、 水 作用下， 以 丙酮 为溶剂， 反应 0.25h， 以53%的产率得到1,3-Dichloro-cyclopenta[c]thiophene-4,6-dione
  参考文献：
  名称：

  First Synthesis of Isothianinhydrin, the Second Thiophene Isostere of Ninhydrin

  摘要：

  报告首次合成了茚三酮的噻吩异构体异噻吩海德林（5,5-二羟基-5,6-二氢-4H-环戊并[c]噻吩-4,6-二酮）及其溴和氯衍生物，并初步评估了它们在指纹检测领域的用途。

  DOI：

  10.1055/s-1999-2845
• 作为产物：
  描述：

  1,3-dichloro-4-oxo-5,6-dihydro-4H-cyclopentathien-6-ylammonium chloride 在 air 、 水 、 sodium nitrite 作用下， 反应 24.0h， 生成 1,3-Dichloro-6-hydroxy-5,6-dihydro-cyclopenta[c]thiophen-4-one
  参考文献：
  名称：

  First Synthesis of Isothianinhydrin, the Second Thiophene Isostere of Ninhydrin

  摘要：

  报告首次合成了茚三酮的噻吩异构体异噻吩海德林（5,5-二羟基-5,6-二氢-4H-环戊并[c]噻吩-4,6-二酮）及其溴和氯衍生物，并初步评估了它们在指纹检测领域的用途。

  DOI：

  10.1055/s-1999-2845

文献信息

• Facile Diastereoselective Routes to Highly Functionalized Cyclopenta[c]thiophenes as Useful Scaffolds in Medicinal Chemistry
  作者：Lan Pham Khanh、Patrick Dallemagne、Sylvain Rault

  DOI：10.1055/s-2002-31960

  日期：——

  The diastereoselective access to highly functionalized cyclopenta[c]thiophene derivatives, potential useful scaffolds in medicinal chemistry, is described starting from aminocyclopenta[c]thiophenones.

  从氨基环戊并[c]噻吩酮开始，描述了非对映选择性地获得高度官能化的环戊并[c]噻吩衍生物的方法，这些衍生物是药物化学中潜在的有用支架。
• Synthesis and biological evaluation of cyclopenta[ c ]thiophene related compounds as new antitumor agents
  作者：Patrick Dallemagne、Lan Pham Khanh、Abdellah Alsaı̈di、Olivier Renault、Isabelle Varlet、Valérie Collot、Ronan Bureau、Sylvain Rault

  DOI：10.1016/s0968-0896(02)00070-6

  日期：2002.7

  A series of 22 cyclopenta[c]thiophene related compounds was obtained by the pharmacomodulation of 6-amino-5,6- dihydro-4H-cyclopenta[c]thiophen-4-ones 1a-g. All compounds were evaluated for potential anticancer activity in the NCI's in vitro human disease-oriented tumor cell line screening panel that consisted of 60 human tumor cell lines arranged in nine subpanels, representing diverse histologies. Among these tested compounds. seven were found to be cytotoxic, especially against leukemia cell lines, allowing us to point out some structure activity relationships. These derivatives were further evaluated for potential in vivo anticancer activity in the hollow fiber assay developed at the NCI, which selected two compounds. If and 3a for standard xenograft testing. (C) 2002 Elsevier Science Ltd. All rights reserved.
• First Synthesis of Isothianinhydrin, the Second Thiophene Isostere of Ninhydrin
  作者：Lan Pham Khanh、Patrick Dallemagne、Sylvain Rault

  DOI：10.1055/s-1999-2845

  日期：1999.9

  The first synthesis of isothianinhydrin (5,5-dihydroxy-5,6-dihydro-4H-cyclopenta[c]thiophene-4,6-dione), a thiophene isostere of ninhydrin, and of its bromo and chloro derivatives, is reported, as well as a preliminary evaluation of their interest in fingerprint detection area.

  报告首次合成了茚三酮的噻吩异构体异噻吩海德林（5,5-二羟基-5,6-二氢-4H-环戊并[c]噻吩-4,6-二酮）及其溴和氯衍生物，并初步评估了它们在指纹检测领域的用途。