5-benzylidene-2-(4-methylphenyl)-1,3-thiazol-4-one

• 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: 5-benzylidene-2-(4-methylphenyl)-1,3-thiazol-4-one
• 化学式: C₁₇H₁₃NOS
• 分子量: 279.362
• InChiKey: GTPGSIOJZRDYST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.43
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-benzylidene-2-(4-methylphenyl)-1,3-thiazol-4-one 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 甲苯 为溶剂， 反应 27.0h， 生成 4-oxo-6-phenyl-2-(p-tolyl)-1,7-dithia-3-azaspiro[4.4]non-2-en-9-yl acetate
  参考文献：
  名称：

  10.1039/d4ob00619d

  摘要：

  DOI：

  10.1039/d4ob00619d

文献信息

• Bifunctional Squaramide‐Catalysed Asymmetric Michael/Hemiketalization/Retro‐Aldol Reaction of Unsaturated Thiazolones with α‐Nitroketones: Synthesis of Chiral 4‐Acyloxythiazole Derivatives
  作者：Yong‐Xing Song、Da‐Ming Du

  DOI：10.1002/adsc.201900901

  日期：2019.11.5

  An efficient and practical organocatalytic asymmetric cascade Michael/hemiketalization/retro‐aldol reaction of unsaturated thiazolones with α‐nitroketones by using cyclohexanediamine‐derived bifunctional squaramide as the catalyst has been developed. Under mild conditions, a broad range of chiral 4‐acyloxythiazole derivatives were obtained in high yields (up to 98% yield) with excellent enantioselectivities

  通过使用环己二胺衍生的双官能方酰胺作为催化剂，开发了一种有效且实用的不饱和噻唑酮与α-硝基酮的有机催化不对称级联迈克尔/半缩醛化/复古-羟醛反应。在温和的条件下，以高收率（最高98％的收率）和出色的对映选择性（最高95％ee）获得了广泛的手性4-酰氧基噻唑衍生物。同时，已经证明了一些合成的转化。
• Asymmetric synthesis of spirooxindole-fused spirothiazolones<i>via</i>squaramide-catalysed reaction of 3-chlorooxindoles with 5-alkenyl thiazolones
  作者：Yong-Xing Song、Da-Ming Du

  DOI：10.1039/c9ob00998a

  日期：——

  An efficient and practical organocatalyzed asymmetric formal [2 + 1] cycloaddition of 3-chlorooxindoles with 5-alkenyl thiazolones by using hydroquinine-derived squaramide as the catalyst has been developed. Under mild conditions, a broad range of spirooxindole-fused spirothiazolones bearing three adjacent stereogenic centers including two vicinal spiro quaternary chiral centers were obtained in high

  通过使用对苯二酚衍生的方酰胺作为催化剂，开发了一种高效且实用的有机催化的3-氯代吲哚与5-烯基噻唑酮的不对称[2 +1]式不对称环加成环。在温和的条件下，可以高产率（高达99％的产率），优异的非对映选择性（高达> 99：1 dr）和对映体选择性获得范围广泛的带有3个相邻立体异构中心（包括两个邻位螺螺旋季手性中心）的螺氧杂吲哚融合的螺噻唑酮。 （最高99％ee）。
• Catalyst-Controlled Diastereoselectivity Switch in the Asymmetric [3 + 2] Annulation of Isatin-Derived MBH Carbonates and 5-Alkenylthiazol-4(5<i>H</i>)-ones
  作者：Ming-Shun Mei、Ya-Jie Wang、Gui-Shan Zhang、Jing-Yi Tang、Ping Tian、Yu-Hui Wang

  DOI：10.1021/acs.orglett.1c02421

  日期：2021.10.1

  Exploration of the diastereodivergent synthesis of spirocyclic oxindoles has been challenging. Herein we report asymmetric [3 + 2] annulations of isatin-derived Morita–Baylis–Hillman (MBH) carbonates and 5-alkenylthiazol-4(5H)-ones. Interestingly, two different chiral catalysts, amide-phosphine and 4-dimethylaminopyridine (DMAP)-thiourea, could lead to two kinds of diastereomeric dispiro oxindoles

  螺环羟吲哚的非对映发散合成的探索一直具有挑战性。在此，我们报告了靛红衍生的 Morita-Baylis-Hillman (MBH) 碳酸盐和 5-alkenylthiazol-4(5 H )-ones 的不对称 [3 + 2] 环化。有趣的是，两种不同的手性催化剂，酰胺-膦和 4-二甲氨基吡啶 (DMAP)-硫脲，可以产生两种具有三个连续立体中心的非对映异构体二螺吲哚。六氟异丙醇 (HFIP) 添加剂在加速反应和调节非对映选择性方面起着至关重要的作用。此外，两种环化加合物都可以进一步转化为结构多样的螺环吲哚。
• N-Heterocyclic Carbene-Catalyzed [3 + 4] Annulation of Enals and Alkenyl Thiazolones: Enantioselective Synthesis of Thiazole-Fused ε-Lactones
  作者：Zhi-Qin Liang、Liang Yi、Kun-Quan Chen、Song Ye

  DOI：10.1021/acs.joc.6b00313

  日期：2016.6.3

  The bifunctional N-heterocyclic carbene catalyzed [3 + 4] annulation of enals and 5-alkenyl thiazolones was developed, giving the corresponding thiazole-fused ε-lactones in high yields with excellent diastereoselectivties and enantioselectivities. The thiazole-fused ε-lactone could be isomerized to the spirocyclic thiazolone–cyclopentanone without erosion of enantioselectivity.

  开发了双功能N-杂环卡宾催化的[3 + 4]环烯和5-烯基噻唑酮的环化反应，以高收率得到了相应的噻唑稠合的ε-内酯，具有出色的非对映选择性和对映选择性。噻唑稠合的ε-内酯可以异构化为螺环噻唑酮-环戊酮，而不会削弱对映选择性。
• Enantioselective synthesis of 7H-pyrano[2,3-d]thiazoles via squaramide-catalyzed [2+4] annulation of malononitrile and 5-ylidenethiazol-4-ones
  作者：Lei Cui、Youming Wang、Zhenghong Zhou

  DOI：10.1016/j.tetasy.2016.08.014

  日期：2016.11

  An efficient catalytic asymmetric synthesis of 7H-pyrano[2,3-d]thiazoles has been developed on the basis of the organocatalyzed [4+2] annulation of malononitrile and 5-ylidenethiazol-4-ones. Under the catalysis of a bifunctional squaramide derived from L-tert-leucine, the reaction of malononitrile and a wide range of 5-ylidenethiazol-4-ones ran smoothly to afford the corresponding structurally diverse 7H-pyrano[2,3-d]thiazole derivatives in good yields (70-94%) and with moderate to excellent enantioselectivities (43->99% ee). (C) 2016 Elsevier Ltd. All rights reserved.