2-溴-5-(2-硝基丙-1-烯基)噻吩 | 124941-12-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 2-溴-5-(2-硝基丙-1-烯基)噻吩
• 英文名称: 2-(2-nitropropen-1-yl)-5-bromothiophene
• 英文别名: 2-(2-nitropropenyl)-5-bromothiophene；Thiophene, 2-bromo-5-(2-nitro-1-propenyl)-；2-bromo-5-(2-nitroprop-1-enyl)thiophene
• CAS: 124941-12-4
• 化学式: C₇H₆BrNO₂S
• 分子量: 248.1
• InChiKey: UHUDRXOZKDYQCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  74.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-溴-5-(2-硝基丙-1-烯基)噻吩 在 盐酸 、 sodium tetrahydroborate 、 硼烷 作用下， 生成 2-(2(RS)-aminopropyl)-5-bromothiophene
  参考文献：
  名称：

  Synthesis and evaluation of radioiodinated 2-(2(RS)-aminopropyl)-5-iodothiophenes as brain imaging agents

  摘要：

  Methods have been developed for the preparation of 2-(2(RS)-aminopropyl)-5-iodothiophenes. The syntheses and physical properties of 2-(2(RS)-aminopropyl)-5-iodothiophene and N-isopropyl-2-(2(RS)-aminopropyl)-5-iodothiophene are described. The radioiodinated agents are of interest because of the high expected uptake and prolonged brain retention that may result from binding to high-capacity, relatively nonspecific amine binding sites. Radioiodine was introduced into the 5-position of 2-(2(RS)-aminopropyl)-5-iodothiophene and N-isopropyl-2-(2(RS)-aminopropyl)-5-iodothiophene by radioiodination of the corresponding 5-boronic acid or 5-(trimethylstannyl) derivatives. Tissue distribution studies in rats with 2-(2(RS)-aminopropyl)-5-[I-126]iodothiophene showed high brain uptake (5 min. 2.77% dose/g 30 min, 2.51% dose/g) and good brain/blood (B/B) ratios (5 min, 6/1; 30 min 3.8/1. A comparison of the brain uptake of the N-isopropyl derivative with the 2(RS)-aminopropyl analogue demonstrated higher initial brain uptake and brain to blood ratios (5 min, 3.2% dose/g; 10.3/1) but more rapid washout (30 min, 1.37% dose; 2.8/1). These data suggest that radiolabeled 2-(2(RS)-aminopropyl)-5-iodothiophenes are potentially useful agents for cerebral perfusion imaging by single-photon-emission computerized tomography (SPECT).

  DOI：

  10.1021/jm00080a012
• 作为产物：
  描述：

  5-溴噻吩-2-甲醛 、 硝基乙烷 在 ammonium acetate 作用下， 反应 7.0h， 以82%的产率得到2-溴-5-(2-硝基丙-1-烯基)噻吩
  参考文献：
  名称：

  Synthesis and evaluation of radioiodinated 2-(2(RS)-aminopropyl)-5-iodothiophenes as brain imaging agents

  摘要：

  Methods have been developed for the preparation of 2-(2(RS)-aminopropyl)-5-iodothiophenes. The syntheses and physical properties of 2-(2(RS)-aminopropyl)-5-iodothiophene and N-isopropyl-2-(2(RS)-aminopropyl)-5-iodothiophene are described. The radioiodinated agents are of interest because of the high expected uptake and prolonged brain retention that may result from binding to high-capacity, relatively nonspecific amine binding sites. Radioiodine was introduced into the 5-position of 2-(2(RS)-aminopropyl)-5-iodothiophene and N-isopropyl-2-(2(RS)-aminopropyl)-5-iodothiophene by radioiodination of the corresponding 5-boronic acid or 5-(trimethylstannyl) derivatives. Tissue distribution studies in rats with 2-(2(RS)-aminopropyl)-5-[I-126]iodothiophene showed high brain uptake (5 min. 2.77% dose/g 30 min, 2.51% dose/g) and good brain/blood (B/B) ratios (5 min, 6/1; 30 min 3.8/1. A comparison of the brain uptake of the N-isopropyl derivative with the 2(RS)-aminopropyl analogue demonstrated higher initial brain uptake and brain to blood ratios (5 min, 3.2% dose/g; 10.3/1) but more rapid washout (30 min, 1.37% dose; 2.8/1). These data suggest that radiolabeled 2-(2(RS)-aminopropyl)-5-iodothiophenes are potentially useful agents for cerebral perfusion imaging by single-photon-emission computerized tomography (SPECT).

  DOI：

  10.1021/jm00080a012

文献信息

• Ring Closure of Nitroalkylmalonates for the Synthesis of Isoxazolines under the Acylation Conditions
  作者：Yulia A. Antonova、Yulia V. Nelyubina、Sema L. Ioffe、Alexey Yu. Sukhorukov、Andrey A. Tabolin

  DOI：10.1002/adsc.202200420

  日期：2022.8.2

  alkyl, and ester) at the C3 and C4 positions of the resulting isoxazolines were also tolerated. A quick assembly of the isoxazoline ring starting from nitroalkenes and malonates was successfully developed. Control experiments showed that the intramolecular ring closure is the most likely key mechanistic step. Subsequent transformations into pyrrolidine and furane derivatives demonstrated the synthetic

  发现硝基烷基丙二酸酯的酰化产生取代的异恶唑啉衍生物。这种氧化还原中性转化具有广泛的底物范围，可生产目标产物，产率高达 92%。在所得异恶唑啉的 C3 和 C4 位置上的各种取代基（芳基、烷基和酯）也是可以接受的。成功开发了以硝基烯烃和丙二酸酯为原料的异恶唑啉环的快速组装。对照实验表明，分子内闭环是最可能的关键机械步骤。随后转化为吡咯烷和呋喃衍生物证明了所得产品的合成效用。
• Goudgaon, Naganna M.; Wadgaonkar, Prakash P.; Kabalka, George W., Synthetic Communications, 1989, vol. 19, # 5and6, p. 805 - 812
  作者：Goudgaon, Naganna M.、Wadgaonkar, Prakash P.、Kabalka, George W.

  DOI：——

  日期：——
• Synthesis and evaluation of radioiodinated 2-(2(RS)-aminopropyl)-5-iodothiophenes as brain imaging agents
  作者：Mark M. Goodman、George W. Kabalka、Ronald C. Marks、F. F. Knapp、J. Lee、Y. Liang

  DOI：10.1021/jm00080a012

  日期：1992.1

  Methods have been developed for the preparation of 2-(2(RS)-aminopropyl)-5-iodothiophenes. The syntheses and physical properties of 2-(2(RS)-aminopropyl)-5-iodothiophene and N-isopropyl-2-(2(RS)-aminopropyl)-5-iodothiophene are described. The radioiodinated agents are of interest because of the high expected uptake and prolonged brain retention that may result from binding to high-capacity, relatively nonspecific amine binding sites. Radioiodine was introduced into the 5-position of 2-(2(RS)-aminopropyl)-5-iodothiophene and N-isopropyl-2-(2(RS)-aminopropyl)-5-iodothiophene by radioiodination of the corresponding 5-boronic acid or 5-(trimethylstannyl) derivatives. Tissue distribution studies in rats with 2-(2(RS)-aminopropyl)-5-[I-126]iodothiophene showed high brain uptake (5 min. 2.77% dose/g 30 min, 2.51% dose/g) and good brain/blood (B/B) ratios (5 min, 6/1; 30 min 3.8/1. A comparison of the brain uptake of the N-isopropyl derivative with the 2(RS)-aminopropyl analogue demonstrated higher initial brain uptake and brain to blood ratios (5 min, 3.2% dose/g; 10.3/1) but more rapid washout (30 min, 1.37% dose; 2.8/1). These data suggest that radiolabeled 2-(2(RS)-aminopropyl)-5-iodothiophenes are potentially useful agents for cerebral perfusion imaging by single-photon-emission computerized tomography (SPECT).