3-nitro-2H-thiochromene | 1338380-75-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫色烯
• 英文名称: 3-nitro-2H-thiochromene
• CAS: 1338380-75-8
• 化学式: C₉H₇NO₂S
• 分子量: 193.226
• InChiKey: YSIZDRBTWMZQBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.14
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-nitro-2H-thiochromene 在 硼烷四氢呋喃络合物 、 碳酸氢钠 、 sodium carbonate 、 magnesium 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 63.42h， 生成 (+/-)-trans-11,12-dimethoxy-6,6a,7,8,9,13b-hexahydrobenzo[d]thiochromeno[3,4-b]azepine
  参考文献：
  名称：

  Assessment of dopamine D1 receptor affinity and efficacy of three tetracyclic conformationally-restricted analogs of SKF38393

  摘要：

  To assess the effect of conformational mobility on receptor activity, the beta-phenyl substituent of dopamine D-1 agonist ligands of the phenylbenzazepine class, (+/-)-6,6a, 7,8,9,13b-hexahydro-5H-benzo[d] naphtho[ 2,1-b] azepine-11,12-diol (8), and its oxygen and sulfur bioisosteres 9 and 10, respectively, were synthesized as conformationally-restricted analogs of SKF38393, a dopamine D-1-selective partial agonist. Compounds trans-8b, 9, and 10 showed binding affinity comparable to that of SKF38393, but functionally, they displayed only very weak agonist activity. These results suggest that the conformationally-restricted structure of the analogs cannot adopt a binding orientation that is necessary for agonist activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.057
• 作为产物：
  描述：

  苯硫酚 在 苯酐 、 正丁基锂 、 四甲基乙二胺 、 二正丁胺 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 3-nitro-2H-thiochromene
  参考文献：
  名称：

  Assessment of dopamine D1 receptor affinity and efficacy of three tetracyclic conformationally-restricted analogs of SKF38393

  摘要：

  To assess the effect of conformational mobility on receptor activity, the beta-phenyl substituent of dopamine D-1 agonist ligands of the phenylbenzazepine class, (+/-)-6,6a, 7,8,9,13b-hexahydro-5H-benzo[d] naphtho[ 2,1-b] azepine-11,12-diol (8), and its oxygen and sulfur bioisosteres 9 and 10, respectively, were synthesized as conformationally-restricted analogs of SKF38393, a dopamine D-1-selective partial agonist. Compounds trans-8b, 9, and 10 showed binding affinity comparable to that of SKF38393, but functionally, they displayed only very weak agonist activity. These results suggest that the conformationally-restricted structure of the analogs cannot adopt a binding orientation that is necessary for agonist activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.057

文献信息

• Enantioselective cascade double Michael addition of 3-nitro-2H-chromenes and acyclic enones: efficient synthesis of functionalized tricyclic chroman derivatives
  作者：Jun-Hua Li、Da-Ming Du

  DOI：10.1039/c5ob01211b

  日期：——

  tetrahydro-6H-benzo[c]chromenes and their derivatives has been developed. The corresponding products were obtained by the cascade double Michael addition of 3-nitro-2H-chromenes and their derivatives with α,β-unsaturated ketones catalyzed by a combination of a quinine-derived primary amine and benzoic acid. Through this methodology, the desired products could be obtained in moderate to good yields (up to

  已经开发出用于不对称构造对映体富集的四氢-6 H-苯并[ c ]色烯及其衍生物的有效方案。相应的产物通过将3-硝基-2 H-色酮及其衍生物与奎宁衍生的伯胺和苯甲酸的组合催化的α，β-不饱和酮进行级联双迈克尔加成而获得。通过这种方法，可以以中等至良好的收率（高达90％），具有优异的非对映选择性（高达> 25：1 dr）和中等至优异的对映选择性（高达95％ee）获得所需的产物。
• Enantioselective synthesis of chiral heterocycles containing both chroman and pyrazolone derivatives catalysed by a chiral squaramide
  作者：Jun-Hua Li、Da-Ming Du

  DOI：10.1039/c4ob02653e

  日期：——

  An efficient chiral squaramide-catalysed enantioselective Michael addition of pyrazolin-5-ones to 3-nitro-2H-chromenes afforded chiral heterocycles containing both chroman and pyrazolone derivatives in high to excellent yields (up to 98%) with high enantioselectivities (up to 96%) under very low catalyst loading (0.2 mol%).

  一个高效的手性方酰胺催化的选择性马克尔加成反应，将吡唑啉-5-酮加到3-硝基-2H-色醇中，得到含有色醇和吡唑酮衍生物的手性杂环化合物，收率高达98%，对映选择性高达96%，在非常低的催化剂负载下（0.2 mol%）。
• Organocatalytic [3 + 2] cycloaddition of oxindole-based azomethine ylides with 3-nitrochromenes: a facile approach to enantioenriched polycyclic spirooxindole-chromane adducts
  作者：Shiqi Wu、Guodong Zhu、Shiqiang Wei、Hongbo Chen、Jingping Qu、Baomin Wang

  DOI：10.1039/c7ob03051g

  日期：——

  An organocatalytic asymmetric [3 + 2] cycloaddition of oxindole-based azomethine ylides with 3-nitro-2H-chromenes has been developed. This reaction provides a facile approach to densely functionalized polycyclic spirooxindole-chromane adducts featuring four contiguous stereogenic centers, including two tetrasubstituted carbon centers. The products were obtained in high yields with good to excellent

  已经开发了基于氧吲哚的偶氮甲亚胺与3-硝基-2 H-色烯的有机催化不对称[3 + 2]环加成反应。该反应为以四个连续的立体中心，包括两个四取代的碳中心为特征的致密官能化的多环螺氧基吲哚-苯并二氢呋喃加合物提供了简便的方法。以高收率获得具有良好至优异的立体选择性的产物（高达99％的收率，96％的ee和> 20：1dr）。另外，可以通过简单的氧化和还原处理容易地衍生化螺[吡咯烷-2，3'-羟吲哚]-苯并二氢吡喃加合物。提出了双重激活的工作模型，以阐明[3 + 2]环加成事件的立体化学过程。