(S)-4-isobutyl-N-propanoyl-1,3-thiazolidine-2-thione | 263764-22-3

• 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: (S)-4-isobutyl-N-propanoyl-1,3-thiazolidine-2-thione
• 英文别名: (S)-4-isobutyl-N-propionylthiazolidine-2-thione；1-[(4S)-4-(2-methylpropyl)-2-sulfanylidene-1,3-thiazolidin-3-yl]propan-1-one
• CAS: 263764-22-3
• 化学式: C₁₀H₁₇NOS₂
• 分子量: 231.383
• InChiKey: JLXYFURLUSZPIE-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  (S)-4-isobutyl-N-propanoyl-1,3-thiazolidine-2-thione 在 四氯化钛 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 (2S,3S)-1-[(4S)-4-isobutyl-2-thioxo-thiazolidin-3-yl]-2-methyl-3-phenyl-3-triethylsilanyl-oxy-propan-1-one
  参考文献：
  名称：

  不对称的羟醛附加：使用四氯化钛和（-）-天冬氨酸来软化N-酰基恶唑烷酮，恶唑烷硫酮和噻唑烷硫酮。

  摘要：

  使用N-酰基氧杂唑烷酮，恶唑烷硫酮和噻唑烷硫酮丙酸酯的氯化钛烯醇盐的不对称羟醛加成物对Evans或非Evans合成产物具有高非对映选择性，这取决于所用碱的性质和量。以1当量的四氯化钛和2当量的（-）-天冬氨酸为碱或1当量的（-）-天冬氨酸和1当量的N-甲基-2-吡咯烷酮，选择性为97：3至> 99：1使用N-丙酰基恶唑烷二酮，恶唑烷硫酮和噻唑烷硫酮获得Evans合成羟醛产物。通过改变路易斯酸/胺碱的比例，可与非恶唑烷硫醇和噻唑烷硫酮一起获得非埃文斯顺醛醇加合物。有人建议在醛醇添加物中的面部选择性的变化是在螯合和非螯合过渡态之间机械途径转换的结果。助剂可以通过亲核酰基取代被还原性去除或裂解。具有高非对映选择性的迭代羟醛序列也可以实现。

  DOI：

  10.1021/jo001387r
• 作为产物：
  描述：

  L-亮氨醇 在 氢氧化钾 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-4-isobutyl-N-propanoyl-1,3-thiazolidine-2-thione
  参考文献：
  名称：

  Titanium Enolates of Thiazolidinethione Chiral Auxiliaries:  Versatile Tools for Asymmetric Aldol Additions

  摘要：

  Asymmetric aldol additions using chlorotitanium enolates of thiazolidinethione propionates proceed with high diastereoselectivity for the "Evans" or "non-Evans" syn product depending on the nature and amount of the base used. With (-)-sparteine as the base, selectivities of 97:3 to >99:1 were obtained for the Evans syn products with 2 equivalents of base and for the non-Evans syn when 1 equiv of base was employed. The thiazolidinethione auxiliaries are easily removed, and the aldol adducts can be readily transformed to various functional groups. Even direct reduction to the aldehyde with diisobutylaluminum hydride is possible.

  DOI：

  10.1021/ol9913901

文献信息

• Synthesis and Fungicidal Activity of Simple Structural 1,3-Thiazolidine-2-Thione Derivatives
  作者：Ning Chen、Hongguang Du、Weidong Liu、Shanshan Wang、Xinyao Li、Jiaxi Xu

  DOI：10.1080/10426507.2014.931399

  日期：2015.1.2

  A series of simple structural 1,3-thiazolidine-2-thione derivatives with various substituents on the S-, N-, 4-, and 5-positions was synthesized with high yields from various vicinal amino alcohols via two steps and screened for their antifungal activity. Bioassay results reveal that some thiazolidine-2-thione derivatives show strong antifungal activities against P. capsici, G. zeae, S. sclerotiorum, A. alternata, B. cinerea, or R. solani. The SAR analysis indicates that N-acyl substituted and 4-alkyl substituents can enhance the antifungal activity. Notably, 4-isopropyl-N-propionylthiazoldine-2-thione shows excellent activity against B. cinerea and G. zeae with IC50 values at 3.7 mu g/mL and 6.5 mu g/mL, respectively, and 4-isobutyl-N-propionylthiazoldine-2-thione shows remarkable fungicidal activity against R. solani, S. sclerotiorum, and G. zeae with IC50 values at 1.0 mu g/mL, 12.1 mu g/mL, and 11.0 mu g/mL, respectively.
• On the influence of chiral auxiliaries in the stereoselective cross-coupling reactions of titanium enolates and acetals
  作者：Jessica Baiget、Annabel Cosp、Erik Gálvez、Loreto Gómez-Pinal、Pedro Romea、Fèlix Urpí

  DOI：10.1016/j.tet.2008.04.044

  日期：2008.6

  Titanium enolates from chiral N-propanoyl-1,3-thiazolidine-2-thiones containing bulky substituents at C4 turned out to be excellent platforms to get highly stereocontrolled cross-coupling reactions with acetals. Related oxazolidinethiones also afforded good results, but the corresponding oxazolidinones resulted completely unselective for such reactions, which proves that an exocyclic C=S bond is essential to attain a synthetically useful stereocontrol. (C) 2008 Elsevier Ltd. All rights reserved.
• Titanium Enolates of Thiazolidinethione Chiral Auxiliaries:  Versatile Tools for Asymmetric Aldol Additions
  作者：Michael T. Crimmins、Kleem Chaudhary

  DOI：10.1021/ol9913901

  日期：2000.3.1

  Asymmetric aldol additions using chlorotitanium enolates of thiazolidinethione propionates proceed with high diastereoselectivity for the "Evans" or "non-Evans" syn product depending on the nature and amount of the base used. With (-)-sparteine as the base, selectivities of 97:3 to >99:1 were obtained for the Evans syn products with 2 equivalents of base and for the non-Evans syn when 1 equiv of base was employed. The thiazolidinethione auxiliaries are easily removed, and the aldol adducts can be readily transformed to various functional groups. Even direct reduction to the aldehyde with diisobutylaluminum hydride is possible.
• Asymmetric Aldol Additions:  Use of Titanium Tetrachloride and (−)-Sparteine for the Soft Enolization of <i>N-</i>Acyl Oxazolidinones, Oxazolidinethiones, and Thiazolidinethiones
  作者：Michael T. Crimmins、Bryan W. King、Elie A. Tabet、Kleem Chaudhary

  DOI：10.1021/jo001387r

  日期：2001.2.1

  N-methyl-2-pyrrolidinone, selectivities of 97:3 to > 99:1 were obtained for the Evans syn aldol products using N-propionyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones. The non-Evans syn aldol adducts are available with the oxazolidinethione and thiazolidinethiones by altering the Lewis acid/amine base ratios. The change in facial selectivity in the aldol additions is proposed to be a result of

  使用N-酰基氧杂唑烷酮，恶唑烷硫酮和噻唑烷硫酮丙酸酯的氯化钛烯醇盐的不对称羟醛加成物对Evans或非Evans合成产物具有高非对映选择性，这取决于所用碱的性质和量。以1当量的四氯化钛和2当量的（-）-天冬氨酸为碱或1当量的（-）-天冬氨酸和1当量的N-甲基-2-吡咯烷酮，选择性为97：3至> 99：1使用N-丙酰基恶唑烷二酮，恶唑烷硫酮和噻唑烷硫酮获得Evans合成羟醛产物。通过改变路易斯酸/胺碱的比例，可与非恶唑烷硫醇和噻唑烷硫酮一起获得非埃文斯顺醛醇加合物。有人建议在醛醇添加物中的面部选择性的变化是在螯合和非螯合过渡态之间机械途径转换的结果。助剂可以通过亲核酰基取代被还原性去除或裂解。具有高非对映选择性的迭代羟醛序列也可以实现。