N-(2-chlorobenzylidene)-4-methylbenzo[d]thiazol-2-amine | 1245712-14-4

• 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: N-(2-chlorobenzylidene)-4-methylbenzo[d]thiazol-2-amine
• CAS: 1245712-14-4
• 化学式: C₁₅H₁₁ClN₂S
• 分子量: 286.785
• InChiKey: IEHLFJQCHAQJFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  25.25
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  亚磷酸二苯酯 、 N-(2-chlorobenzylidene)-4-methylbenzo[d]thiazol-2-amine 在 C₂₉H₂₈F₆N₄OS 作用下， 以 二氯甲烷 为溶剂， 反应 12.5h， 以96%的产率得到(S)-O,O'-diphenyl 1-(4-methylbenzo[d]thiazol-2-ylamino)-1-(2-chlorophenyl)methylphosphonate
  参考文献：
  名称：

  Asymmetric Synthesis and Bioselective Activities of α-Amino-phosphonates Based on the Dufulin Motif

  摘要：

  The asymmetric synthesis of enantiomerically pure alpha-aminophosphonates with high and bioselective activities is a challenge. Here, we report that both enantiomers of a-aminophosphonates bearing the N-benzothiazole moiety can be prepared in high yields (up to 99%) and excellent enantioselectivities (up to 99% ee) by using chiral thiourea organocatalysts. Evaluation of the antiviral activities of our reaction products against cucumber mosaic virus (CMV) led to promising hits with high and selective biological activities, wherein (R)-enantiomers exhibit higher biological activities than the corresponding (S)-enantiomers. Especially, compound (R)-3b with excellent anti-CMV activity (curative activity, 72.3%; protection activity, 56.9%; and inactivation activity, 96.9%) at 500 mu g/mL emerged as a potential inhibitor of the plant virus. The difference in the selective bioactivity could be affected by the combination mode of the three-dimensional space between the enantiomers of alpha-aminophosphonate and cucumber mosaic virus coat protein (CMV-CP) via florescence spectroscopy and molecular docking.

  DOI：

  10.1021/acs.jafc.6b01256
• 作为产物：
  描述：

  2-氨基-4-甲基苯并噻唑 、 2-氯苯甲醛 以 甲苯 为溶剂， 以76%的产率得到N-(2-chlorobenzylidene)-4-methylbenzo[d]thiazol-2-amine
  参考文献：
  名称：

  通过金鸡纳生物碱衍生物催化的曼尼希型反应对映选择性合成带有苯并噻唑部分的β-氨基酯

  摘要：

  在新型手性金鸡纳生物碱硫脲催化剂存在下，通过不同亚胺与丙二酸酯的曼尼希型反应，以高对映选择性（高达 95% ee）获得了具有生物活性苯并噻唑部分的新型 β-氨基酯。发现衍生自芳香醛和杂环醛的亚胺可用于这种转化。

  DOI：

  10.1002/ejoc.201100351

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 Cinchona Alkaloid-Thiourea Catalyzed Mannich Reaction for Enantioselective Synthesis of β-Amino Ketones Bearing Benzothiazol Moiety
  作者：Peng Lin、Baoan Song、Pinaki S. Bhadury、Deyu Hu、Yuping Zhang、Linhong Jin、Song Yang

  DOI：10.1002/cjoc.201180413

  日期：2011.11

  were effectively catalyzed by the modified chiral cinchona alkaloid‐derived thiourea. The reactions led to chiral β‐amino carbonyl compounds in high yields and good enantioselectivities. The study demonstrated for the first time that Mannich reactions of unmodified acetylacetone with heterocyclic imine derived from benzothiazole can be promoted by chiral bifunctional organocatalyst.

  改良的手性金鸡纳生物碱衍生的硫脲可有效催化亚胺与乙酰丙酮的曼尼希反应。反应导致高收率和良好的对映选择性的手性β-氨基羰基化合物。该研究首次证明，手性双功能有机催化剂可促进未修饰的乙酰丙酮与衍生自苯并噻唑的杂环亚胺的曼尼希反应。
• Chiral cinchona alkaloid-derived thiourea catalyst for enantioselective synthesis of novel β-amino esters by mannich reaction
  作者：Weihua Li、Baoan Song、Pinaki S. Bhadury、Liang Li、Zhenchao Wang、Xiaoyan Zhang、Deyu Hu、Zhuo Chen、Yuping Zhang、Song Bai、Jian Wu、Song Yang

  DOI：10.1002/chir.21986

  日期：2012.3

  designed to access new asymmetric β‐amino esters bearing benzothiazole moiety by utilizing a Mannich reaction between an imine and a malonate. A simultaneous activation of the two imine functionalities and malonate by the bifunctional chiral organocatalyst is proposed to account for the good yields (71–91%) and high enantiomeric excess (89.4–98.5%) under mild conditions. Chirality © 2012 Wiley Periodicals

  通过使用亚胺和丙二酸酯之间的曼尼希反应，设计了金鸡纳生物碱衍生的硫脲催化剂，以获取带有苯并噻唑部分的新型不对称β-氨基酯。有人提出，在温和条件下，双功能手性有机催化剂同时激活两个亚胺官能团和丙二酸酯，可得到良好的收率（71-91％）和高的对映体过量（89.4-98.5％）。手性©2012 Wiley Periodicals，Inc.