(S)-N-butanoyl-4-isopropyl-1,3-thiazolidine-2-thione | 117606-74-3

• 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)-N-butanoyl-4-isopropyl-1,3-thiazolidine-2-thione
• 英文别名: 2-Thiazolidinethione, 4-(1-methylethyl)-3-(1-oxobutyl)-, (4S)-；1-[(4S)-4-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-3-yl]butan-1-one
• CAS: 117606-74-3
• 化学式: C₁₀H₁₇NOS₂
• 分子量: 231.383
• InChiKey: DHIAIYZBQPQVCD-MRVPVSSYSA-N

物化性质

• 沸点：
  312.7±25.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

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：

  Alpha-甲基苯乙酸甲酯 、 (S)-N-butanoyl-4-isopropyl-1,3-thiazolidine-2-thione 在 六甲基磷酰三胺 、 lithium cyclohexylisopropylamide 作用下， 生成 methyl (2S)-2-methyl-3-oxo-2-phenylhexanoate
  参考文献：
  名称：

  Highly enantioselective Claisen-type acylation and Dieckmann annulation

  摘要：

  DOI：

  10.1021/jo00260a040
• 作为产物：
  描述：

  (S)-4-异丙基噻唑烷-2-硫 、 丁酰氯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.83h， 以74%的产率得到(S)-N-butanoyl-4-isopropyl-1,3-thiazolidine-2-thione
  参考文献：
  名称：

  Stereoselective Alkylation of (S)-N-Acyl-4-isopropyl-1,3-thiazolidine-2-thiones Catalyzed by (Me₃P)₂NiCl₂

  摘要：

  The structurally simple (Me3P)(2)NiCl2 complex catalyzes S(N)1-type alkylations of chiral N-acyl thiazolidinethiones with diarylmethyl methyl ethers and other stable carbenium cations. The former can contain a variety of functional groups and heteroatoms at the alpha-position. The resultant adducts are isolated as single diastereomers in high yields and can be converted into enantiomerically pure derivatives in a straightforward manner.

  DOI：

  10.1021/acs.orglett.5b01626

文献信息

• Stereoselective Synthesis of the C9–C19 Fragment of Peloruside A
  作者：Stuart C. D. Kennington、Juan M. Romo、Pedro Romea、Fèlix Urpí

  DOI：10.1021/acs.orglett.6b01428

  日期：2016.6.17

  A concise synthesis of the C9–C19 fragment of peloruside A that is both highly stereoselective and efficient is described. Achieving an overall yield of 23% over 14 steps, this synthesis not only is high yielding but also involves four chromatography steps. This approach is based on the addition of metal enolates of chiral auxiliary scaffolds generated by either catalytic or stoichiometric amounts

  描述了脑白蛋白A的C9–C19片段的简洁合成，该片段具有很高的立体选择性和效率。通过14个步骤可实现23％的总产率，该合成不仅产率高，而且涉及四个色谱步骤。该方法基于通过催化或化学计量的镍（II）或钛（IV）路易斯酸生成的手性辅助支架的金属烯醇盐的添加。
• Diastereoselective and Catalytic α-Alkylation of Chiral <i>N</i>-Acyl Thiazolidinethiones with Stable Carbocationic Salts
  作者：Stuart C. D. Kennington、Mònica Ferré、Juan Manuel Romo、Pedro Romea、Fèlix Urpí、Mercè Font-Bardia

  DOI：10.1021/acs.joc.7b00657

  日期：2017.6.16

  nickel-catalyzed alkylation of chiral N-acyl-4-isopropyl-1,3-thiazolidine-2-thiones using a commercially available nickel(II) complex, (Me3P)2NiCl2, has been developed for tropylium and trityl tetrafluoroborate salts. The reaction provides a single diastereomer of the corresponding adducts in good to high yields, which, in turn, can be easily converted into a wide array of enantiomerically pure compounds that

  已经开发了用于对和三苯甲基的镍的手性N-酰基-4-异丙基-1,3-噻唑烷-2-硫酮的直接镍催化的烷基化反应，使用市售的镍（II）配合物（Me 3 P）2 NiCl 2。四氟硼酸盐。该反应以高产率至高产率提供了相应的加合物的单一非对映异构体，进而可以容易地转化成对映体纯的化合物的广泛范围，这些化合物很难通过其他不对称方法获得。
• Stereoselective Synthesis of the Western Hemisphere of Salinomycin
  作者：Igor Larrosa、Pedro Romea、Fèlix Urpí

  DOI：10.1021/ol052900w

  日期：2006.2.1

  [structure: see text]. A convergent and module-based strategy for the asymmetric synthesis of the western hemisphere (C1-C17 fragment) of salinomycin has been devised. This new synthetic approach relies on highly stereoselective C-glycosidation and aldol processes.

  [结构：见文字]。已经设计了基于收敛和基于模块的盐霉素的西半球（C1-C17片段）不对称合成策略。这种新的合成方法依赖于高度立体选择性的C-糖基化和羟醛工艺。
• Highly enantioselective Claisen-type acylation and Dieckmann annulation
  作者：Yoshimitsu Nagao、Yuichi Hagiwara、Toshiaki Tohjo、Yukari Hasegawa、Masahito Ochiai、Motoo Shiro

  DOI：10.1021/jo00260a040

  日期：1988.12
• Stereoselective Alkylation of (<i>S</i>)-<i>N</i>-Acyl-4-isopropyl-1,3-thiazolidine-2-thiones Catalyzed by (Me₃P)₂NiCl₂
  作者：Javier Fernández-Valparís、Juan Manuel Romo、Pedro Romea、Fèlix Urpí、Hubert Kowalski、Mercè Font-Bardia

  DOI：10.1021/acs.orglett.5b01626

  日期：2015.7.17

  The structurally simple (Me3P)(2)NiCl2 complex catalyzes S(N)1-type alkylations of chiral N-acyl thiazolidinethiones with diarylmethyl methyl ethers and other stable carbenium cations. The former can contain a variety of functional groups and heteroatoms at the alpha-position. The resultant adducts are isolated as single diastereomers in high yields and can be converted into enantiomerically pure derivatives in a straightforward manner.