2-(4-chloro-benzylidene)-benzo[b]thiophen-3-one | 3139-46-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(4-chloro-benzylidene)-benzo[b]thiophen-3-one
• 英文别名: 3-Oxo-2-<4-chlor-benzyliden>-2,3-dihydro-thionaphthen；2-[(4-Chlorophenyl)methylidene]-1-benzothiophen-3-one
• CAS: 3139-46-6
• 化学式: C₁₅H₉ClOS
• 分子量: 272.755
• InChiKey: SMLJRVPSANIUBT-UHFFFAOYSA-N

物化性质

• 熔点：
  159.5-161.5 °C
• 沸点：
  440.0±45.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-chloro-benzylidene)-benzo[b]thiophen-3-one 、 2-benzyl 4-((2,2,2-trifluoroethyl)imino)isoquinoline-1,3(2H,4H)-dione 在 三乙烯二胺 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以91%的产率得到2''-benzyl-4'-(4-chlorophenyl)-5'-(trifluoromethyl)-1''H,3H-dispiro[benzo[b]thiophene-2,3'-pyrrolidine-2',4''-isoquinoline]-1'',3,3''(2''H)-trione
  参考文献：
  名称：

  Diastereoselective Construction of CF ₃ ‐Containing Bispiro[isoquinolone‐pyrrolidine‐benzothiophenone]s through 1,3‐Dipolar Cycloaddition

  摘要：

  AbstractA new protocol to access CF3‐containing bispiro[isoquinolone‐pyrrolidine‐benzothiophenone]s was described. A series of 1,3‐dipoles were synthesized from isoquinolinetrione and CF3CH2NH2. In the presence of 10 mol% DABCO, the 1,3‐dipolar cycloaddition of isoquinolinedione trifluoroethyl ketimines and unsaturated benzothiophenones delivered corresponding adducts in excellent yields (up to 98 %) and diastereoselectivities (up to >20 : 1 dr).

  DOI：

  10.1002/ejoc.202200645

文献信息

• Catalytic asymmetric aromatizing inverse electron-demand [4+2] cycloaddition of 1-thioaurones and 1-azaaurones
  作者：Shu-Pei Yuan、Pei-Hao Dou、Yun-Qing Jia、Jian-Qiang Zhao、Yong You、Zhen-Hua Wang、Ming-Qiang Zhou、Wei-Cheng Yuan

  DOI：10.1039/d1cc06357j

  日期：——

  Using 1-thioaurones and 1-azaaurones as electron-deficient oxa-dienes, an organocatalytic asymmetric aromatizing inverse electron-demand [4+2] cycloaddition with γ-deconjugated butenolides and azlactones was developed. A wide range of optically active benzothiophene-fused δ-lactones and indole-fused δ-lactones were obtained with desirable outcomes (up to 94% yield, >99 : 1 dr and 99% ee).

  以1-硫代金酮和1-氮杂金酮作为缺电子氧杂二烯，开发了γ-去共轭丁烯内酯和吖内酯的有机催化不对称芳构化逆电子需求[4+2]环加成反应。以理想的结果获得了范围广泛的光学活性苯并噻吩稠合 δ-内酯和吲哚稠合 δ-内酯（高达 94% 的产率，>99:1 dr 和 99% ee）。
• A squaramide-catalysed asymmetric cascade Michael addition/acyl transfer reaction between unsaturated benzothiophenones and α-nitroketones
  作者：Cheng Niu、Da-Ming Du

  DOI：10.1039/d1ob02217b

  日期：——

  was developed using unsaturated benzothiophenones and α-nitroketones catalysed by bifunctional squaramide via Michael addition and acyl transfer steps. A broad range of chiral acyloxybenzothiophene derivatives were obtained in good yields (up to 97%) with excellent enantioselectivities (up to 98% ee). What's more, employing different chiral squaramide catalysts and unsaturated benzothiophenones can

  使用由双功能方酰胺通过迈克尔加成和酰基转移步骤催化的不饱和苯并噻吩酮和α-硝基酮，开发了一种有效且实用的有机催化不对称策略。以良好的收率（高达 97%）和优异的对映选择性（高达 98% ee）获得了范围广泛的手性酰氧基苯并噻吩衍生物。更重要的是，采用不同的手性方酰胺催化剂和不饱和苯并噻吩酮可以在苯并噻吩的2-位或3-位传递​​酰氧基单元。
• Diastereoselective Construction of CF ₃ ‐Containing Bispiro[isoquinolone‐pyrrolidine‐benzothiophenone]s through 1,3‐Dipolar Cycloaddition
  作者：Cheng Niu、Da‐Ming Du

  DOI：10.1002/ejoc.202200645

  日期：2022.7.14

  AbstractA new protocol to access CF3‐containing bispiro[isoquinolone‐pyrrolidine‐benzothiophenone]s was described. A series of 1,3‐dipoles were synthesized from isoquinolinetrione and CF3CH2NH2. In the presence of 10 mol% DABCO, the 1,3‐dipolar cycloaddition of isoquinolinedione trifluoroethyl ketimines and unsaturated benzothiophenones delivered corresponding adducts in excellent yields (up to 98 %) and diastereoselectivities (up to >20 : 1 dr).