(S)‐4‐isobutylthiazolidine‐2‐thione | 185137-28-4

• 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: (S)‐4‐isobutylthiazolidine‐2‐thione
• 英文别名: (S)-4-isobutyl-1,3-thiazolidine-2-thione；(S)-4-(isobutyl)-2-thiazolidinethione；(S)-4-isobutylthiazolidine-2-thione；(S)-4-i-butylthiazolidine-2-thione；(4S)-4-(2-methylpropyl)-1,3-thiazolidine-2-thione
• CAS: 185137-28-4
• 化学式: C₇H₁₃NS₂
• 分子量: 175.319
• InChiKey: YTCCBPWGHFWCNS-LURJTMIESA-N

物化性质

• 熔点：
  48-50 °C
• 沸点：
  242.3±23.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)‐4‐isobutylthiazolidine‐2‐thione 在 四氯化钛 、 三乙胺 、 鹰爪豆碱 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3R)-3-hydroxy-1-[(4S)-4-isobutyl-2-thioxo-thiazolidin-3-yl]-2,5-dimethyl-hexan-1-one
  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
• 作为产物：
  描述：

  L-亮氨醇 在 盐酸 、 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 生成 (S)‐4‐isobutylthiazolidine‐2‐thione
  参考文献：
  名称：

  Yadav; Dubey, Suman, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 3, p. 593 - 595

  摘要：

  DOI：

文献信息

• Asymmetric transfer hydrogenation of ketones using Ru(0) nanoparticles modified by Chiral Thiones
  作者：Noor U. Din Reshi、Dineshchakravarthy Senthurpandi、Ashoka G. Samuelson

  DOI：10.1002/aoc.4885

  日期：2019.5

  The catalytic asymmetric transfer hydrogenation (ATH) of acetophenone in isopropanol by Ru(0) nanoparticles (NPs) obtained by the in‐situ reduction of Ru (II) half‐sandwich complexes of chiral 2‐oxazolidinethiones and 2‐thiozolidinethiones was examined and compared with the catalytic activity of Ru(0) NPs formed in‐situ by the reduction of [Ru(p‐cymene)(Cl)2]2 in presence of optically active ligands

  考察并比较了通过手性2-恶唑烷硫酮和2-硫唑烷硫酮的Ru（II）半三明治复合物原位还原得到的Ru（0）纳米颗粒（NPs）在异丙醇中对苯乙酮的催化不对称转移氢化（ATH）通过还原[Ru（对伞花烃）（Cl）2 ] 2原位形成Ru（0）NPs的催化活性（S）-4-异丁基噻唑烷-2-硫酮，（S）-4-异丙基-2-（-2-吡啶基）-2-恶唑啉，（8S，9R）-（-）-辛可尼定，（S）-亮氨酸，（S）-苯丙氨醇和（S）-亮氨酸。然后检查了三个最佳的催化体系中十三种具有不同电子和空间特性的芳族酮的ATH。使用苯乙酮TH中Ru（II）半三明治复合物与（S）-4-异丁基噻唑烷-2-硫酮的NP最多可得到24％ee。通过TEM和DLS测量来表征NP。动力学研究和中毒实验证实，该反应是由原位形成的手性NP催化的。还进行了复合物的完整表征，包括两个复合物的X射线晶体学表征。
• A Versatile Synthesis of Various Substituted Taurines from Vicinal Amino Alcohols and Aziridines
  作者：Ning Chen、Weiyi Jia、Jiaxi Xu

  DOI：10.1002/ejoc.200900759

  日期：2009.11

  Taurine and structurally diverse substituted taurines have been synthesized by peroxyformic acid oxidation of the thiazolidine-2-thione intermediates generated from vicinal amino alcohols or aziridines and carbon disulfide. Thestereochemistry and mechanisms of the reactions are disscussed. The method is a salt-free and versatile route, convenient in terms of purification, and can be used to synthesize

  牛磺酸和结构不同的取代牛磺酸已经通过由邻氨基醇或氮丙啶和二硫化碳产生的噻唑烷-2-硫酮中间体的过氧甲酸氧化合成。讨论了反应的立体化学和机理。该方法为无盐通用路线，纯化方便，可用于合成光学活性取代牛磺酸。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Total Synthesis of (+)-Laurencin:  An Asymmetric Alkylation−Ring-Closing Metathesis Approach to Medium Ring Ethers
  作者：Michael T. Crimmins、Kyle A. Emmitte

  DOI：10.1021/ol991201e

  日期：1999.12.1

  enantioselective total synthesis of (+)-laurencin 1 is achieved in 18 steps from (S)-(+)-4-benzyl-3-benzyloxyacetyl-2-oxazolidinone. The key steps in this synthesis are an asymmetric glycolate alkylation leading to acyl oxazolidinone 2 and a subsequent ring-closing olefin metathesis to construct the oxocene core of 1. The approach to medium ring ethers utilized in this synthesis provides a general and efficient

  [式：见正文]（+）-劳伦霉素1的对映选择性全合成是由（S）-（+）-4-苄基-3-苄氧基乙酰基-2-恶唑烷酮分十八步完成的。该合成过程中的关键步骤是导致酰基恶唑烷酮2的不对称乙醇酸酯烷基化反应和随后的闭环烯烃复分解反应，以构建1的茂新烯核。用于该合成反应的中环醚的方法为合成该化合物提供了一条通用而有效的途径。其他海洋天然产物的循环核心。
• Stereoselective synthesis of maresin 1
  作者：Jørn E. Tungen、Marius Aursnes、Trond Vidar Hansen

  DOI：10.1016/j.tetlet.2015.02.080

  日期：2015.4

  Maresin 1 is a potent anti-inflammatory and pro-resolving lipid mediator derived from docosahexaenoic acid. The total synthesis of maresin 1 is achieved in 10 steps and in 7% overall yield. The Evans–Nagao aldol reaction between (2E,4E)-5-bromopenta-2,4-dienal and different chiral auxiliaries is investigated. The reported synthesis is efficient and highly stereoselective, affording multi-milligram

  Maresin 1是衍生自二十二碳六烯酸的有效消炎和促分解脂质介质。Maresin 1的总合成可通过10个步骤完成，总产率为7％。研究了（2 E，4 E）-5-溴戊达2,4-二烯醛与不同手性助剂之间的Evans–Nagao羟醛反应。报道的合成是有效的和高度立体选择性的，提供了数毫克量的这种生物学上有趣的脂质介体。
• 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.