(4-Methoxy-phenyl)-[1-thiazol-2-yl-meth-(E)-ylidene]-amine | 294872-67-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4-Methoxy-phenyl)-[1-thiazol-2-yl-meth-(E)-ylidene]-amine
• 英文别名: N-(4-methoxyphenyl)-1-(1,3-thiazol-2-yl)methanimine
• CAS: 294872-67-6
• 化学式: C₁₁H₁₀N₂OS
• 分子量: 218.279
• InChiKey: IFFTYCYZWJGEMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-Methoxy-phenyl)-[1-thiazol-2-yl-meth-(E)-ylidene]-amine 在 甲醇 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (3S,4S)-3-Hydroxy-1-(4-methoxy-phenyl)-4-thiazol-2-yl-azetidin-2-one
  参考文献：
  名称：

  New highly active taxoids from 9β-dihydrobaccatin-9,10-acetals. Part 5

  摘要：

  To improve the metabolic stability of 3, which exhibited both in vitro antitumor activity and in vivo efficacy by both iv and po administration, we designed and synthesized new taxane analogues. Most of the synthetic compounds maintained excellent antitumor activity and were scarcely metabolized by human liver microsomes. And some compounds exhibited potent antitumor effects against B16 melanoma BL6 in vivo by both iv and po administration similarly to 3. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.109
• 作为产物：
  描述：

  2-醛基噻唑 、 甲氧苯胺 在 sodium sulfate 作用下， 以 二氯甲烷 为溶剂， 生成 (4-Methoxy-phenyl)-[1-thiazol-2-yl-meth-(E)-ylidene]-amine
  参考文献：
  名称：

  超越生物等排体：从双环丁烷中分散合成氮杂双环己烷和环丁烯胺**

  摘要：

  通过利用双环丁烷与亚胺加成的不同反应性，可以很容易地获得高度官能化和立体化学定义的氮杂双环己烷和环丁烯胺。这些模块化合成提供了新的和选择性的方法来制备富含 C sp 3的支架，在药物化学中具有超越生物等排替代物的潜力。

  DOI：

  10.1002/anie.202204719

文献信息

• Stereoselective Synthesis of Densely Functionalized Pyrrolidin-2-ones by a Conjugate Addition/Nitro-Mannich/Lactamization Reaction
  作者：James C. Anderson、Lisa R. Horsfall、Andreas S. Kalogirou、Matthew R. Mills、Gregory J. Stepney、Graham J. Tizzard

  DOI：10.1021/jo301000r

  日期：2012.7.20

  Copper-catalyzed conjugate addition of diorgano zinc reagents to nitroacrylate 1 followed by a subsequent nitro-Mannich reaction and in situ lactamization leads to an efficient one-pot synthesis of 1,3,5-trisubstituted 4-nitropyrrolidin-2-ones (5). The versatility of the reaction is shown for a wide range of N-p-(methoxy)phenyl protected aldimines 3 derived from alkyl, aryl, and heteroaryl aldehydes

  铜催化的将二有机锌试剂共轭添加到硝酸丙烯酸酯1中，随后进行硝基曼尼希反应和原位内酰胺化，可有效地一锅合成1,3,5-三取代的4-硝基吡咯烷酮-2-酮（5） 。该反应的通用性示出了用于范围广泛的ñ - p - （甲氧基）苯基保护的醛亚胺3选自烷基，芳基，和杂芳基的醛衍生的。致密官能化的吡咯烷酮-2-酮5分离为单一非对映异构体（40个实例，产率33-84％）。二乙基锌的对映选择性铜催化共轭加成导致高度结晶的产物，该产物可以高收率重结晶为对映纯度。研究了一系列成功的化学选择性转化，拓宽了吡咯烷-2-酮作为立体化学纯的结构单元用于进一步有机合成的适用性。
• The Ru3(CO)12-Catalyzed Intermolecular [2 + 2 + 1] Cyclocoupling of Imines, Alkenes or Alkynes, and Carbon Monoxide: A New Synthesis of Functionalized γ-Lactams
  作者：Naoto Chatani、Mamoru Tobisu、Taku Asaumi、Shinji Murai

  DOI：10.1055/s-2000-6295

  日期：——

  The reaction of imines which contain N-heterocycles or an ester group with alkenes or alkynes and carbon monoxide in the presence of a catalytic amount of a ruthenium carbonyl results in [2 + 2 + 1] cyclocoupling to give γ-butyrolactams in good yields.

  含有N-杂环或酯基的亚胺与烯烃或炔烃及一氧化碳在催化量的钌羰基存在下反应，导致[2 + 2 + 1]环偶联，生成γ-丁内酯，产率良好。
• New highly active taxoids from 9β-dihydrobaccatin-9,10-acetals. Part 5
  作者：Yasuyuki Takeda、Kouichi Uoto、Michio Iwahana、Takeshi Jimbo、Motoko Nagata、Ryo Atsumi、Chiho Ono、Noriko Tanaka、Hirofumi Terasawa、Tsunehiko Soga

  DOI：10.1016/j.bmcl.2004.03.109

  日期：2004.6

  To improve the metabolic stability of 3, which exhibited both in vitro antitumor activity and in vivo efficacy by both iv and po administration, we designed and synthesized new taxane analogues. Most of the synthetic compounds maintained excellent antitumor activity and were scarcely metabolized by human liver microsomes. And some compounds exhibited potent antitumor effects against B16 melanoma BL6 in vivo by both iv and po administration similarly to 3. (C) 2004 Elsevier Ltd. All rights reserved.
• Beyond Bioisosteres: Divergent Synthesis of Azabicyclohexanes and Cyclobutenyl Amines from Bicyclobutanes**
  作者：Kushal Dhake、Kyla J. Woelk、Joseph Becica、Andy Un、Sarah E. Jenny、David C. Leitch

  DOI：10.1002/anie.202204719

  日期：2022.7.4

  By exploiting the divergent reactivity of bicyclobutanes undergoing addition to imines, highly-functionalized and stereochemically-defined azabicyclohexanes and cyclobutenyl amines are easily accessible. These modular syntheses provide new and selective methods to prepare Csp3-rich scaffolds with potential beyond bioisosteric replacements in medicinal chemistry.

  通过利用双环丁烷与亚胺加成的不同反应性，可以很容易地获得高度官能化和立体化学定义的氮杂双环己烷和环丁烯胺。这些模块化合成提供了新的和选择性的方法来制备富含 C sp 3的支架，在药物化学中具有超越生物等排替代物的潜力。