3-isopropyl-5-methyl-2-thioxothiazolidin-4-one | 98431-58-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-isopropyl-5-methyl-2-thioxothiazolidin-4-one
• 英文别名: 3-isopropyl-5-methylthiazolidin-4-on-2-thione；3-isopropyl-5-methyl-2-thioxo-thiazolidin-4-one；3-Isopropyl-5-methyl-2-thioxo-thiazolidin-4-on；5-Methyl-3-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 98431-58-4
• 化学式: C₇H₁₁NOS₂
• 分子量: 189.302
• InChiKey: KSQXKRXMICBDGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  77.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-isopropyl-5-methyl-2-thioxothiazolidin-4-one 、 苄叉丙酮 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97%的产率得到3-isopropyl-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：

  异硫氰酸异丙酯 、 硫代乳酸 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 3-isopropyl-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

• 一种3,3二取代羟基吲哚化合物的合成方法
  申请人：深圳市众康动保科技有限公司

  公开号：CN108456205B

  公开（公告）日：2021-06-04

  本发明公开了一种3,3二取代羟基吲哚化合物的合成方法，包括以下步骤：步骤1)，将反应原料化合物(1)和化合物(2)混合加入反应器中，步骤2)，加入双功能催化剂，再加入反应溶剂反应，反应温度为0‑80℃，反应时间为11‑12h，获得3,3二取代羟基吲哚化合物；其中，化合物(1)的化学式为：化合物(2)的化学式为：多取代吡唑类化合物的化学式为R1、R2、R3和R4均为烷基、芳香基或杂环中的任一种。采用本发明中的合成方法，反应操作比较简单，反应条件温和，产率较高，适合大规模工业化生产。
• Enantioselective Construction of Vicinal Sulfur-containing Tetrasubstituted Stereocenters via Organocatalyzed Mannich-Type Addition of Rhodanines to Isatin Imines
  作者：Qiuhong Huang、Lili Zhang、Yuyu Cheng、Pengfei Li、Wenjun Li

  DOI：10.1002/adsc.201800642

  日期：2018.9.3

  isatin‐derived imines as suitable partners under chiral squaramide catalysis. By using this strategy, the resulting 3‐substituted 3‐amino‐2‐oxindoles featuring both rhodanine and vicinal sulfur‐containing tetrasubstituted stereocenters structural motifs were obtained in high yields with excellent enantioselectivities and diastereoselectivities.

  罗丹烷的催化对映体选择性亲核加成反应是通过在手性方酰胺催化下，使用以伊斯兰为基础的亚胺作为合适的配体而建立的。通过使用该策略，可以高收率获得具有出色的对映选择性和非对映选择性的具有罗丹宁和邻位硫的四取代立体中心结构基序的3-取代的3-氨基-2-氧吲哚。
• Pettersson, Ingrid; Rang, Knut; Sandstroem, Jan, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 9, p. 751 - 756
  作者：Pettersson, Ingrid、Rang, Knut、Sandstroem, Jan

  DOI：——

  日期：——
• PETTERSSON I.; RANG K.; SANDSTROM J., ACTA CHEM. SCAND., 40,(1986) N 9, 751-756
  作者：PETTERSSON I.、 RANG K.、 SANDSTROM J.

  DOI：——

  日期：——
• 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.