4-methyl-1-(2-thioxothiazolidin-3-yl)pentan-1-one

• 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: 4-methyl-1-(2-thioxothiazolidin-3-yl)pentan-1-one
• 英文别名: N-(4-methylpentanoyl)-1,3-thiazolidine-2-thione；4-Methyl-1-(2-sulfanylidene-1,3-thiazolidin-3-yl)pentan-1-one；4-methyl-1-(2-sulfanylidene-1,3-thiazolidin-3-yl)pentan-1-one
• 化学式: C₉H₁₅NOS₂
• 分子量: 217.356
• InChiKey: JEELMDGBLAPGKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  4-methyl-1-(2-thioxothiazolidin-3-yl)pentan-1-one 、 原甲酸三甲酯 在 2,6-二甲基吡啶 、 [Ni((S)-Tol-BINAP)]OTf₂ 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (R)-2-(dimethoxymethyl)-4-methyl-1-(2-thioxothiazolidin-3-yl)pentan-1-one 、 (S)-2-(dimethoxymethyl)-4-methyl-1-(2-thioxothiazolidin-3-yl)pentan-1-one
  参考文献：
  名称：

  Ni(II) Tol-BINAP-Catalyzed Enantioselective Orthoester Alkylations of N-Acylthiazolidinethiones

  摘要：

  The development of a Ni(II) (S)-Tol-BINAP-catalyzed enantioselective alkylation of N-acylthiazolidinethiones with trimethyl orthoformate is described. The reaction is general with respect to the thiazolidinethione, providing the desired adducts in good to excellent yield and with high levels of enantioselectivity (11 examples, 51-92% yield, 90-99% ee). The products are readily converted into a variety of synthetically useful derivatives in a straightforward manner.

  DOI：

  10.1021/ja053386s
• 作为产物：
  描述：

  异己酰氯 、 2-巯基噻唑啉 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以74%的产率得到4-methyl-1-(2-thioxothiazolidin-3-yl)pentan-1-one
  参考文献：
  名称：

  Ni(II) Tol-BINAP-Catalyzed Enantioselective Orthoester Alkylations of N-Acylthiazolidinethiones

  摘要：

  The development of a Ni(II) (S)-Tol-BINAP-catalyzed enantioselective alkylation of N-acylthiazolidinethiones with trimethyl orthoformate is described. The reaction is general with respect to the thiazolidinethione, providing the desired adducts in good to excellent yield and with high levels of enantioselectivity (11 examples, 51-92% yield, 90-99% ee). The products are readily converted into a variety of synthetically useful derivatives in a straightforward manner.

  DOI：

  10.1021/ja053386s

文献信息

• Direct and Enantioselective Aldol Reactions Catalyzed by Chiral Nickel(II) Complexes
  作者：Stuart C. D. Kennington、Saul F. Teloxa、Miguel Mellado‐Hidalgo、Oriol Galeote、Sabrina Puddu、Marina Bellido、Pedro Romea、Fèlix Urpí、Gabriel Aullón、Mercè Font‐Bardia

  DOI：10.1002/anie.202104352

  日期：2021.7.5

  A direct and asymmetric aldol reaction of N-acyl thiazinanethiones with aromatic aldehydes catalyzed by chiral nickel(II) complexes is reported. The reaction gives the corresponding O-TIPS-protected anti-aldol adducts in high yields and with remarkable stereocontrol and atom economy. Furthermore, the straightforward removal of the achiral scaffold provides enantiomerically pure intermediates of synthetic

  报道了由手性镍 (II) 配合物催化的N-酰基噻嗪烷硫酮与芳香醛的直接和不对称醛醇反应。该反应以高产率和显着的立体控制和原子经济性得到相应的O -TIPS 保护的抗醛醇加合物。此外，非手性支架的直接去除提供了合成感兴趣的对映异构纯中间体，其中涉及抗-α-氨基-β-羟基和α，β-二羟基羧酸衍生物的前体。理论计算解释了观察到的高立体控制。
• EIGHT-ARM POLYETHYLENE GLYCOL DERIVATIVE, PRODUCTION METHOD THEREFOR, AND MODIFIEDBIO-RELATEDSUBSTANCETHEREOF
  申请人：XIAMEN SINOPEG BIOTECH CO., LTD

  公开号：US20180214561A1

  公开（公告）日：2018-08-02

  Disclosed are an eight-arm polyethylene glycol (PEG) derivative (formula I), production method therefor and modified bio-related substance thereby. Wherein, one tetravalent group U together with four trivalent groups E c form a highly symmetrical octavalent group CORE 0 ; L c connects the octavalent group to eight PEG chains having polydispersity or monodispersity and having n 1 to n 8 as the degree of polymerization thereof; the terminal of one PEG chain is connected to at least one functional group F (k≥1); said PEG chain and F therebetween can be directly connected (g=0) or be indirectly connected via a linking group L 0 to a terminal end-branching group G (g=1); the latter provides more reactive sites for binding more drug molecules and increases the drug loading. The eight-arm polyethylene glycol derivative has a centrosymmetric or approximately centrosymmetric structure, and leads to more precise control of the molecular weight in large-scale production and much narrower distribution of molecular weight for products. The modified bio-related substance thereby has a more uniform and controllable performance.