1-(4-bromophenyl)-N-(6-methoxy-1,3-benzothiazol-2-yl)methanimine | 96717-95-2

• 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: 1-(4-bromophenyl)-N-(6-methoxy-1,3-benzothiazol-2-yl)methanimine
• CAS: 96717-95-2
• 化学式: C₁₅H₁₁BrN₂OS
• 分子量: 347.235
• InChiKey: VLMNHXZJFXAYGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  34.48
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenyl)-1-(1H-pyrazol-1-yl)ethanone 、 1-(4-bromophenyl)-N-(6-methoxy-1,3-benzothiazol-2-yl)methanimine 在 N-乙基哌啶 、 (S)-(+)-5,5'-双[二(3,5-二叔丁基-4-甲氧基苯基)膦]-4,4'-二-1,3-苯并二氧戊环 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 以79%的产率得到(2S,3R)-2-(4-bromophenyl)-3-(4-chlorophenyl)-8-methoxy-2,3-dihydro-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-4-one
  参考文献：
  名称：

  非对映体和对映体选择性曼尼希/环化级联反应接近手性苯并噻唑并嘧啶衍生物

  摘要：

  一种有效的不对称曼尼希/环化级联策略是从2-苯并噻唑啉与N-酰基吡唑建立的，以使用铜基络合物提供光学活性的苯并噻唑并嘧啶衍生物。温和的级联过程构建了各种结构多样的产品，具有广泛的底物范围，同时具有出色的对映选择性（高达99％ee）和非对映选择性（高达99：1 dr）。

  DOI：

  10.1002/chem.202005509
• 作为产物：
  描述：

  2-氨基-6-甲氧基苯并噻唑 、 对溴苯甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 1-(4-bromophenyl)-N-(6-methoxy-1,3-benzothiazol-2-yl)methanimine
  参考文献：
  名称：

  Benzothiazole Schiff-bases as potential imaging agents for β-amyloid plaques in Alzheimer’s disease

  摘要：

  A series of benzothiazole Schiff-bases as potential diagnostic imaging agents targeting beta-amyloid (A beta) plaques in Alzheimer's disease (AD) were synthesized and evaluated. When in vitro binding studies using AD homogenate with [I-125] 6-iodo-2-(4'-dimethyl- amino)-phenyl-imidazo[1,2-alpha]pyridine ([I-125]IMPY) as the reference ligand were carried out with the derivatives, the compounds showed high to low binding affinities for AD homogenate at the K (i) values ranged from 4.38 to 514.65 nM, depending on the substitution on the phenyl ring. Fluorescent staining in vitro showed that one compound with a N,N-dimethylamino group intensely stained A beta plaques within brain sections of postmortem AD patients. The results strongly suggest that these derivatives are worthy of further study and may be a useful amyloid imaging agents for early detection of amyloid plaques in the brain of AD.

  DOI：

  10.1007/s00044-012-0416-0

文献信息

• Asymmetric Synthesis of α-Amino Phosphonates by Using Cinchona Alkaloid-Based Chiral Phase Transfer Catalyst
  作者：Weihua Li、Yifeng Wang、Danqian Xu

  DOI：10.1002/ejoc.201801013

  日期：2018.10.24

  imines catalyzed by a cinchona alkaloid‐based chiral phase‐transfer catalyst has been developed. The process affords the desired hydrophosphonylation of imine products with quaternary stereocenters in good to high yields (up to 95 % yield) and excellent enantioselectivities (up to 99 % ee). And this straightforward protocol can be applied to gram scale reaction effectively.

  已经开发了一种基于对金鸡纳生物碱的手性相转移催化剂催化的亚磷酸酯向多功能亚胺的高度对映选择性亲核加成反应。该方法以高到高的产率（高达95％的产率）和优异的对映选择性（高达99％的ee）提供了具有季立构中心的亚胺产物的所需的氢膦酰基化。而且这种简单的协议可以有效地应用于革兰氏反应。
• Chiral phosphoric acid-catalyzed enantioselective construction of structurally diverse benzothiazolopyrimidines
  作者：Lucie Jarrige、Danijel Glavač、Guillaume Levitre、Pascal Retailleau、Guillaume Bernadat、Luc Neuville、Géraldine Masson

  DOI：10.1039/c8sc05581e

  日期：——

  A highly efficient catalytic enantioselective [4+2] cycloaddition was developed between 2-benzothiazolimines and enecarbamates. A wide range of benzothiazolopyrimidines bearing three contiguous stereogenic centers was obtained in high to excellent yields and with excellent diastereo- and enantioselectivities (d.r. > 98 : 2 and up to >99% ee). Furthermore, this chiral phosphoric acid-catalyzed strategy

  在2-苯并噻唑亚胺和烯氨基甲酸酯之间开发了一种高效催化对映选择性[4+2]环加成反应。以高至优异的收率获得了多种带有三个连续立体中心的苯并噻唑并嘧啶，并具有优异的非对映和对映选择性（dr > 98 : 2 和高达 > 99% ee）。此外，这种手性磷酸催化策略具有可扩展性，并且能够获得一类新型光学纯路易斯碱异硫脲衍生物。
• Diastereo‐ and Enantioselective Mannich/Cyclization Cascade Reaction Access to Chiral Benzothiazolopyrimidine Derivatives
  作者：Yan Zhang、Jia‐Hui Yang、Ying‐Qi Xia、Lin Dong、Fen‐Er Chen

  DOI：10.1002/chem.202005509

  日期：2021.4.7

  An efficient asymmetric Mannich/cyclization cascade strategy was established from 2‐benzothiazolimines with N‐acylpyrazoles to provide optical active benzothiazolopyrimidine derivatives using a copper‐based complex. The mild cascade process constructed various structurally diverse products with broad scope of substrates together with excellent enantioselectivities (up to 99 % ee) and diastereoselectivities

  一种有效的不对称曼尼希/环化级联策略是从2-苯并噻唑啉与N-酰基吡唑建立的，以使用铜基络合物提供光学活性的苯并噻唑并嘧啶衍生物。温和的级联过程构建了各种结构多样的产品，具有广泛的底物范围，同时具有出色的对映选择性（高达99％ee）和非对映选择性（高达99：1 dr）。
• Benzothiazole Schiff-bases as potential imaging agents for β-amyloid plaques in Alzheimer’s disease
  作者：Changsheng Gan、Lin Zhou、Zhenzhen Zhao、Haoshu Wang

  DOI：10.1007/s00044-012-0416-0

  日期：2013.9

  A series of benzothiazole Schiff-bases as potential diagnostic imaging agents targeting beta-amyloid (A beta) plaques in Alzheimer's disease (AD) were synthesized and evaluated. When in vitro binding studies using AD homogenate with [I-125] 6-iodo-2-(4'-dimethyl- amino)-phenyl-imidazo[1,2-alpha]pyridine ([I-125]IMPY) as the reference ligand were carried out with the derivatives, the compounds showed high to low binding affinities for AD homogenate at the K (i) values ranged from 4.38 to 514.65 nM, depending on the substitution on the phenyl ring. Fluorescent staining in vitro showed that one compound with a N,N-dimethylamino group intensely stained A beta plaques within brain sections of postmortem AD patients. The results strongly suggest that these derivatives are worthy of further study and may be a useful amyloid imaging agents for early detection of amyloid plaques in the brain of AD.