3-methyl-N-nitroso-2(3H)-benzothiazole imine | 19617-04-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 3-methyl-N-nitroso-2(3H)-benzothiazole imine
• 英文别名: 3-methyl-2-nitrosiminobenzothiazoline；2-Nitrosimino-3-methyl-2,3-dihydro-benthiazol；(3-methyl-3H-benzothiazol-2-ylidene)-nitroso-amine；(NZ)-N-(3-methyl-1,3-benzothiazol-2-ylidene)nitrous amide
• CAS: 19617-04-0
• 化学式: C₈H₇N₃OS
• 分子量: 193.229
• InChiKey: ZCIOGZSBJLPYFS-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  70.3
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-methyl-N-nitroso-2(3H)-benzothiazole imine 以46%的产率得到
  参考文献：
  名称：

  AKIBA K.; KAWAMURA T.; HISAOKA M.; INAMOTO N., BULL. CHEM. SOC. JAP. , 1975, 48, NO 11, 3262-3265

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲基-2-亚氨基苯并噻唑 在 溶剂黄146 、 sodium nitrite 作用下， 以75.6%的产率得到3-methyl-N-nitroso-2(3H)-benzothiazole imine
  参考文献：
  名称：

  Experimental and Theoretical Studies on the Thermal Decomposition of Heterocyclic Nitrosimines¹

  摘要：

  A series of substituted 2-nitrosiminobenzothiazolines (2) were synthesized by the nitrosation of the corresponding 2-iminobenzothiazolines (6). Thermal decomposition of 2a-f and of the seleno analogue 7 in methanol and of 3-methyl-2-nitrosobenzothiazoline (2a) in acetonitrile, 1,4-dioxane, and cyclohexane followed first-order kinetics. The activation parameters for thermal deazetization of 2a were measured in cyclohexane (DeltaH(double dagger) = 25.3 +/- 0.5 kcal/mol, DeltaS(double dagger) = 1.3 +/- 1.5 eu) and in methanol (DeltaH(double dagger) = 22.5 +/- 0.7 kcal/mol, DeltaS(double dagger) = -12.9 +/- 2.1 eu). These results indicate a unimolecular decomposition and are consistent with a proposed stepwise mechanism involving cyclization of the nitrosimine, followed by loss of N-2. The ground-state conformations of the parent nitrosiminothiazoline (9a) and transition states for rotation around the exocyclic C=N bond, electrocyclic ring closure, and loss of N-2 were calculated using A initio molecular orbital theory at the MP2/6-31G* level. The calculated gas-phase barrier height for the loss of N-2 from 9a (25.2 kcal/mol, MP4(SDQ, FC)/6-31G*//MP2/6-31G* + ZPE) compares favorably with the experimental barrier for 2a of 25.3 kcal/mol in cyclohexane. The potential energy surface is unusual; the rotational transition state 9a-rot-ts connects directly to the orthogonal transition state for ring-closure 9aTS. The decoupling of rotational and pseudopericyclic bond-forming transition states is contrasted with the single pericyclic transition state (15TS) for the electrocyclic ring-opening of oxetene (15) to acrolein (16). For comparison, the calculated homolytic strength of the N-NO bond is 40.0 kcal/mol (MP4(SDQ, FC)/6-31G*//MP2/6-31G* + ZPE).

  DOI：

  10.1021/ja010659k

文献信息

• New NO-Donors with Antithrombotic and Vasodilating Activities, VIII: Benzothiazole-2(3H)-nitrosimines
  作者：Klaus Rehse、Thomas Ciborski、Eberhard Lüdtke

  DOI：10.1002/ardp.19943271204

  日期：——

  Thirty title compounds were prepared and tested for their antiplatelet activity in the Born‐test. Five nitrosimines inhibit the aggregation induced by collagen in concentrations below 10 μmol/L halfmaximally. Four compounds were investigated in an in vivo thrombosis model. An inhibition of thrombosis between 29 and 53% was observed in mesenteric arterioles of rats 2 h after p.o. administration (60

  制备了 30 种标题化合物，并在 Born 试验中测试了它们的抗血小板活性。5 种亚硝胺在低于 10 μmol/L 的浓度下最大抑制胶原蛋白聚集。在体内血栓形成模型中研究了四种化合物。口服给药 (60 mg/kg) 后 2 小时，在大鼠的肠系膜小动脉中观察到血栓形成的抑制率为 29% 至 53%。对静脉的影响不太明显（10-22%）。对于一种化合物，口服应用 4 小时后仍可证明这些作用。
• HISAOKA M.; AKIBA K.; INAMOTO N., BULL. CHEM. SOC. JAP. <BCSJ-A8>, 1975, 48, NO 11, 3266-3269
  作者：HISAOKA M.、 AKIBA K.、 INAMOTO N.

  DOI：——

  日期：——
• HISAOKA M.; AKIBA K.; INAMOTO N., BULL. CHEM. SOC. JAP. <BCSJ-A8>, 1975, 48, NO 11, 3274-3277
  作者：HISAOKA M.、 AKIBA K.、 INAMOTO N.

  DOI：——

  日期：——
• AKIBA K.; HISAOKA M.; KAWAMURA T.; INAMOTO N., BULL. CHEM. SOC. JAP. <BCSJ-A8>, 1975, 48, NO 11, 3270-3273
  作者：AKIBA K.、 HISAOKA M.、 KAWAMURA T.、 INAMOTO N.

  DOI：——

  日期：——
• AKIBA K.; KAWAMURA T.; OCHIUMI M.; INAMOTO N., BULL. CHEM. SOC. JAP. <BCSJ-A8>, 1976, 49, NO 7, 1913-1916
  作者：AKIBA K.、 KAWAMURA T.、 OCHIUMI M.、 INAMOTO N.

  DOI：——

  日期：——