3-benzylbenzo[d]thiazol-2(3H)-imine | 65948-22-3

• 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-benzylbenzo[d]thiazol-2(3H)-imine
• 英文别名: 3-benzyl-2-iminobenzothiazoline；3-benzyl-3H-benzothiazol-2-one-imine；3-Benzyl-3H-benzothiazol-2-on-imin；3-Benzyl-2-iminobenzothiazole；3-benzyl-1,3-benzothiazol-2-imine
• CAS: 65948-22-3
• 化学式: C₁₄H₁₂N₂S
• 分子量: 240.329
• InChiKey: HEHNGGKJGNBCKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-benzylbenzo[d]thiazol-2(3H)-imine 在 溶剂黄146 、 sodium nitrite 作用下， 以83%的产率得到3-benzyl-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
• 作为产物：
  描述：

  3-苄基苯并噻唑鎓 在 碘 、 potassium carbonate 、 sodium amide 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以76%的产率得到3-benzylbenzo[d]thiazol-2(3H)-imine
  参考文献：
  名称：

  唑类 的无金属C（sp 2）–H官能化：K 2 CO 3 / I 2介导的氧化，氨基化和氨基化†

  摘要：

  通过使用可商购的简单K 2 CO 3 / I 2试剂组合，可以实现多种唑类的直接C2-H氧化和亚胺化。碘化唑加成物，产生通过所述原位生成N-杂环碳烯的，为C2-H氧化，亚胺化，和唑类的胺化的关键中间体。重要的是，这些反应在温和的条件下以高至优异的产率进行，可扩展至大量并显示出广泛的底物范围。有趣的是，这种直接的C2-H胺化方法使我们能够获得各种具有药理活性的N 6-烷基或N 6芳基取代的苯并咪唑并喹唑啉酮骨架通过分子内CH串联进行一锅反应。

  DOI：

  10.1039/c8ob00535d

文献信息

• Benzothiazole derivative
  申请人：Hodogaya Chemical Co., Ltd.

  公开号：US05095025A1

  公开（公告）日：1992-03-10

  A benzothiazole derivative represented by the general formula: ##STR1## wherein X represents --NHR, --R or --OR group in which R is a lower alkyl, cycloalkyl, aryl or substituted aryl group; Y represents a lower alkyl, alkenyl, alkyloxycarbonylalkyl, benzyl or substituted benzyl group; and Z represents a lower alkoxy group or a hydrogen atom. This compound is useful as an active ingredient of an agricultural and horticultural fungicide.

  一种苯并噻唑衍生物，其一般式表示为：##STR1## 其中X代表--NHR、--R或--OR基团，其中R为较低的烷基、环烷基、芳基或取代芳基基团；Y代表较低的烷基、烯基、烷氧羰基烷基、苄基或取代苄基基团；Z代表较低的烷氧基或氢原子。此化合物可作为农业和园艺杀菌剂的活性成分。
• BENZOTHIAZOLE DERIVATIVES AS FUNGICIDE
  申请人：HODOGAYA CHEMICAL COMPANY, LIMITED

  公开号：EP0407621A1

  公开（公告）日：1991-01-16

  The invention relates to a benzothiazole derivative represented by general formula (I), wherein X is NHR, R or OR; R is lower alkyl, cycloalkyl, aryl or substituted aryl; Y is lower alkyl, alkenyl, alkyloxycarbonylalkyl, benzyl or substituted benzyl; and Z is lower alkoxy or hydrogen. This compound is useful as an active ingredient of agrohorticultural bactericides.

  本发明涉及一种由通式（I）表示的苯并噻唑衍生物，其中 X 是 NHR、R 或 OR；R 是低级烷基、环烷基、芳基或取代芳基；Y 是低级烷基、烯基、烷氧羰基烷基、苄基或取代苄基；Z 是低级烷氧基或氢。该化合物可用作农用园艺杀菌剂的活性成分。
• Tuppack,H.-J., Diss. <Bonn 1954> S. 64
  作者：Tuppack,H.-J.

  DOI：——

  日期：——
• US5095025A
  申请人：——

  公开号：US5095025A

  公开（公告）日：1992-03-10