3-(4-methoxyphenyl)-5-methyl-2-thioxothiazolidin-4-one | 16711-84-5

• 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: 3-(4-methoxyphenyl)-5-methyl-2-thioxothiazolidin-4-one
• 英文别名: 3-(4-methoxy-phenyl)-5-methyl-2-thioxo-thiazolidin-4-one；5-Methyl-3-(4-methoxy-phenyl)-rhodanin；3-[p-Methoxyphenyl]-5-methylrhodanine；3-(4-methoxyphenyl)-5-methyl-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 16711-84-5
• 化学式: C₁₁H₁₁NO₂S₂
• 分子量: 253.346
• InChiKey: LFOHTIRZXHBXJJ-UHFFFAOYSA-N

物化性质

• 沸点：
  382.8±44.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  86.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苄叉丙酮 、 3-(4-methoxyphenyl)-5-methyl-2-thioxothiazolidin-4-one 在 (R)-3-methoxy-N1,N1-dimethyl-3,3-diphenylpropane-1,2-diamine 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 48.0h， 以98%的产率得到3-(4-methoxyphenyl)-5-methyl-5-(3-oxo-1-phenylbutyl)-2-thioxothiazolidin-4-one
  参考文献：
  名称：

  Asymmetric Michael Addition of Substituted Rhodanines to α,β-Unsaturated Ketones Catalyzed by Bulky Primary Amines

  摘要：

  A bulky group was introduced by design into a diamine catalyst, and a series of robust and tunable bulky chiral primary amine catalysts were developed and successfully applied in the direct conjugate addition of substituted rhodanines to alpha,beta-unsaturated ketones. High yields (up to 99%) and excellent diastereoselectivities (up to 99:1 dr) and enantioselectivities (up to 98% ee) were observed.

  DOI：

  10.1021/ol300489q
• 作为产物：
  描述：

  硫代乳酸 、 4-甲氧基苯基 异硫氰酸酯 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 3-(4-methoxyphenyl)-5-methyl-2-thioxothiazolidin-4-one
  参考文献：
  名称：

  Asymmetric Michael Addition of Substituted Rhodanines to α,β-Unsaturated Ketones Catalyzed by Bulky Primary Amines

  摘要：

  A bulky group was introduced by design into a diamine catalyst, and a series of robust and tunable bulky chiral primary amine catalysts were developed and successfully applied in the direct conjugate addition of substituted rhodanines to alpha,beta-unsaturated ketones. High yields (up to 99%) and excellent diastereoselectivities (up to 99:1 dr) and enantioselectivities (up to 98% ee) were observed.

  DOI：

  10.1021/ol300489q

文献信息

• Enantioselective γ -addition reaction of rhodanines to allenoates catalyzed by chiral phosphine-carbamate
  作者：Tian-Chen Kang、Lu-Ping Wu、Feng Sha、Xin-Yan Wu

  DOI：10.1016/j.tet.2017.12.050

  日期：2018.3

  Phosphine-catalyzed enantioselective γ-additions of rhodanines to allenoates have been developed for the first time. With the employment of chiral cyclohexane-based phosphines, a wide range of substituted rhodanine derivatives containing tertiary chiral centers were constructed in good yields and high enantioselectivities.

  首次开发了膦催化罗丹宁对烯酸酯的对映体选择性γ-加成反应。随着手性环己烷基膦的使用，以高收率和高对映选择性构建了多种包含叔手性中心的取代的若丹宁衍生物。
• Enantioselective Mannich reaction between rhodanines and isatin-derived ketimines to construct vicinal tetrasubstituted stereocenters
  作者：Han Xu、Tian-Chen Kang、Feng Sha、Xin-Yan Wu

  DOI：10.1039/c8ob01524d

  日期：——

  enantioselective Mannich reaction between rhodanines and isatin-derived ketimines was developed. With 2 mol% of a quinine-based tertiary amine-thiourea catalyst C2, 3,3-disubstituted oxindoles with vicinal tetrasubstituted stereocenters were obtained in moderate-to-excellent yields (43–99%) with excellent diastereoselectivities (98 : 2–99 : 1 dr) and good-to-excellent enantioselectivities (up to 97% ee). The

  研发了罗丹宁与伊斯汀衍生的酮亚胺之间的有机催化对映选择性曼尼希反应。使用2 mol％的奎宁基叔胺-硫脲催化剂C2，可以以中等至优异的收率（43–99％）获得具有出色的非对映选择性（98：2–99）的具有邻位四取代立体中心的3,3-二取代的羟吲哚。 ：1博士）和良好到优秀的对映选择性（高达97％ee）。容易获得的底物，低催化剂负载量和高立体选择性是主要特征。
• 3-Phenylrhodanines as potential antimalarial agents
  作者：Leslie M. Werbel、Nancy Headen、Edward F. Elslager

  DOI：10.1021/jm00308a040

  日期：1968.3
• Asymmetric Michael Addition of Substituted Rhodanines to α,β-Unsaturated Ketones Catalyzed by Bulky Primary Amines
  作者：Feng Yu、Haoxiang Hu、Xiaodong Gu、Jinxing Ye

  DOI：10.1021/ol300489q

  日期：2012.4.20

  A bulky group was introduced by design into a diamine catalyst, and a series of robust and tunable bulky chiral primary amine catalysts were developed and successfully applied in the direct conjugate addition of substituted rhodanines to alpha,beta-unsaturated ketones. High yields (up to 99%) and excellent diastereoselectivities (up to 99:1 dr) and enantioselectivities (up to 98% ee) were observed.