(S)-4-isopropyl-N-(2-pivaloyloxyacetyl)-1,3-thiazolidine-2-thione | 1400585-44-5

• 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-isopropyl-N-(2-pivaloyloxyacetyl)-1,3-thiazolidine-2-thione
• 英文别名: [2-oxo-2-[(4S)-4-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-3-yl]ethyl] 2,2-dimethylpropanoate
• CAS: 1400585-44-5
• 化学式: C₁₃H₂₁NO₃S₂
• 分子量: 303.447
• InChiKey: UQGBRPQYGWKHRT-SECBINFHSA-N

物化性质

• 沸点：
  384.5±44.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-4-isopropyl-N-(2-pivaloyloxyacetyl)-1,3-thiazolidine-2-thione 在 4-二甲氨基吡啶 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 8.58h， 生成
  参考文献：
  名称：

  Stereoselective synthesis of C-glycosides by addition of titanium enolates from a chiral N-glycolyl thiazolidinethione to glycals

  摘要：

  The Lewis acid-mediated addition of the titanium enolate from the pivaloyl-protected (S) N-glycolyl-4-isopropyl-1,3-thiazolidine-2-thione to glycals affords the corresponding syn C-alpha-glycosides in high yields and excellent diastereomeric ratios. Further removal of the chiral auxiliary permits access to enantiomerically pure C1'-pivaloyloxy pyrans in a straightforward manner. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.028
• 作为产物：
  描述：

  三甲基乙酰氯 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 76.0h， 生成 (S)-4-isopropyl-N-(2-pivaloyloxyacetyl)-1,3-thiazolidine-2-thione
  参考文献：
  名称：

  镍（II）配合物催化的手性N-羟乙酰基噻唑烷硫酮与乙缩醛的直接抗乙醇酸羟醛缩醛反应

  摘要：

  极少量的市售且易于处理的（Me 3 P）2 NiCl 2触发了手性N -2-新戊酰氧基乙酰基噻唑烷硫酮7在缩醛中的立体选择性羟醛加成反应，从而以高效的方式提供了相应的抗乙醇酸酯加合物。

  DOI：

  10.1002/ejoc.201901097

文献信息

• Diastereoselective Methyl Orthoformate Alkylations of Chiral<i>N</i>-Acylthiazolidinethiones Catalyzed by Nickel(II) Complexes
  作者：Juan Manuel Romo、Erik Gálvez、Ignasi Nubiola、Pedro Romea、Fèlix Urpí、Max Kindred

  DOI：10.1002/adsc.201300521

  日期：2013.10.11

  AbstractThe completely diastereoselective silyl triflate‐mediated methyl orthoformate alkylation of chiral N‐acyl‐4‐isopropyl‐1,3‐thiazolidine‐2‐thiones catalyzed by commercially available nickel(II) complexes is reported. The simple experimental procedure requires 2.5–5 mol% of bis(phosphine)nickel dichloride [(R3P)2NiCl2] complexes, proceeds under very mild conditions, and covers a wide array of acyl groups. Furthermore, it can potentially be expanded to different electrophiles.magnified image
• Diastereoselective Additions of Titanium Enolates from <i>N</i>-Glycolyl Thiazolidinethiones to Acetals
  作者：Jessica Baiget、Marta Caba、Erik Gálvez、Pedro Romea、Fèlix Urpí、Mercè Font-Bardia

  DOI：10.1021/jo301569x

  日期：2012.10.5

  The stereochemical outcome of the Lewis acid-mediated glycolate addition of the titanium enolates from protected N-hydroxyacetyl-4-isopropyl-1,3-thiazolidine-2-thiones to dimethyl and dibenzyl acetals depends on the hydroxyl protecting group. Particularly, the pivaloyl protected glycolate derivative provides the reluctant anti adducts in high yields and diastereomeric ratios, which can be isolated and further converted in enantiomerically pure form to beta-methoxy or beta-benzyloxy alpha-pivaloyloxy carbonyl fragments in a straightforward manner.
• 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.
• Stereoselective synthesis of C-glycosides by addition of titanium enolates from a chiral N-glycolyl thiazolidinethione to glycals
  作者：Erik Gálvez、Miriam Sau、Pedro Romea、Fèlix Urpí、Mercè Font-Bardia

  DOI：10.1016/j.tetlet.2013.01.028

  日期：2013.3

  The Lewis acid-mediated addition of the titanium enolate from the pivaloyl-protected (S) N-glycolyl-4-isopropyl-1,3-thiazolidine-2-thione to glycals affords the corresponding syn C-alpha-glycosides in high yields and excellent diastereomeric ratios. Further removal of the chiral auxiliary permits access to enantiomerically pure C1'-pivaloyloxy pyrans in a straightforward manner. (C) 2013 Elsevier Ltd. All rights reserved.
• Direct <i>anti</i> Glycolate Aldol Reaction of Protected Chiral <i>N</i> -Hydroxyacetyl Thiazolidinethiones with Acetals Catalyzed by a Nickel(II) Complex
  作者：Juan Manuel Romo、Pedro Romea、Fèlix Urpí

  DOI：10.1002/ejoc.201901097

  日期：2019.9.30

  Tiny amounts of commercially available and easy to handle (Me3P)2NiCl2 trigger the stereoselective aldol addition of chiral N‐2‐pivaloyloxyacetyl thiazolidinethione 7 to acetals to provide the corresponding anti glycolate adducts in a highly efficient manner.

  极少量的市售且易于处理的（Me 3 P）2 NiCl 2触发了手性N -2-新戊酰氧基乙酰基噻唑烷硫酮7在缩醛中的立体选择性羟醛加成反应，从而以高效的方式提供了相应的抗乙醇酸酯加合物。