[(5S)-2,2-Bis(trifluoromethyl)-4-oxo-1,3-dioxolan-5-yl] acetic acid | 172540-27-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(5S)-2,2-Bis(trifluoromethyl)-4-oxo-1,3-dioxolan-5-yl] acetic acid
• 英文别名: [(5S)-2,2-bis(trifluoromethyl)-4-oxo-1,3-dioxolan-5-yl]acetic acid；(5S)-2,2-Bis(trifluoromethyl)-4-oxo-1,3-dioxolan-5-ylacetic acid；2,2-bis(trifluoromethyl)-1,3-dioxolan-4-one；2-[(4S)-5-oxo-2,2-bis(trifluoromethyl)-1,3-dioxolan-4-yl]acetic acid
• CAS: 172540-27-1
• 化学式: C₇H₄F₆O₅
• 分子量: 282.096
• InChiKey: AKAMXKBFJWZRDT-REOHCLBHSA-N

物化性质

• 沸点：
  309.1±37.0 °C(Predicted)
• 密度：
  1.719±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(5S)-2,2-Bis(trifluoromethyl)-4-oxo-1,3-dioxolan-5-yl] acetic acid 在 氯化亚砜 、 叠氮基三甲基硅烷 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 46.0h， 生成 5-<(5S)-<(9-Fluorenylmethoxycarbonyl)amino>methyl>-2,2-bis(trifluoromethyl)-1,3-dioxolan-4-one
  参考文献：
  名称：

  New Efficient Strategy for the Incorporation of (S)-Isoserine into Peptides

  摘要：

  A new efficient synthesis of (S)-isoserine derivatives from (S)-malic acid using hexafluoroacetone as protecting and activating reagent is described. Via this route (S)-isoserine is obtained as mono- and diactivated species suitable for the incorporation of isoserine into the N- and C-terminal positions of peptides.

  DOI：

  10.1021/jo00128a042
• 作为产物：
  描述：

  L-苹果酸 、 六氟丙酮 生成 [(5S)-2,2-Bis(trifluoromethyl)-4-oxo-1,3-dioxolan-5-yl] acetic acid
  参考文献：
  名称：

  六氟丙酮作为保护和活化试剂：新型氟取代的α-氨基、α-羟基和α-巯基酸的合成

  摘要：

  从(S)-天冬氨酸、(S)-苹果酸、(S)-柠苹果酸和(S,R)-硫代苹果酸开始，新型4,4-二氟取代的α-氨基-、α-羟基-和α-巯基戊酸已被合成，使用六氟丙酮作为保护和活化试剂。新的部分氟化的α-官能化羧酸代表了用于肽和缩肽修饰以及合理设计和阐明二级结构的有趣单体。

  DOI：

  10.1055/s-2004-829131

文献信息

• Hexafluoroacetone as a Protecting and Activating Reagent. Regioselective Esterification of Aspartic, Malic, and Thiomalic Acid
  作者：Ksenia Pumpor、Elisabeth Windeisen、Jan Spengler、Fernando Albericio、Klaus Burger

  DOI：10.1007/s00706-004-0183-9

  日期：2004.11

  Hexafluoroacetone reacts with α-functionalized α,β-dicarboxy acids like aspartic, malic, and thiomalic acid to give exclusively five-membered lactones. The β-carboxylic groups remain unaffected and can be derivatized separately. They can be linked i.a. to orthogonal protecting groups or multivalent alcohols like pentaerythritol to give synthetically valuable building blocks.

  六氟丙酮与α-官能化的α，β-二羧酸（如天冬氨酸，苹果酸和硫代苹果酸）反应，仅生成五元内酯。β-羧基不受影响，可以单独衍生。它们可以连接 IA 以正交的保护基或多价醇如季戊四醇给予综合有价值的积木。
• Synthesis of the molecular hybrid inspired by Largazole and Psammaplin A
  作者：Xiaoling Yu、Bingbing Zhang、Guangsheng Shan、Yue Wu、Feng-Ling Yang、Xinsheng Lei

  DOI：10.1016/j.tet.2017.12.025

  日期：2018.2

  distinguishing examples, Largazole and Psammaplin A, which possess macrocyclic depsipeptide and simple linear amide scaffold respectively, we designed one novel molecular hybrid by replacing the alkene moiety in Largazole with a semirigid amide bond. This hybrid compound has been synthesized from l-malic acid in 10 steps with an overall yield of 7%. The preliminary biological assays suggest that the replacement

  HDAC（组蛋白去乙酰化酶）抑制剂的重要一类是具有结构多样性的含硫海洋天然产物。受两个分别具有大环depsipeptide和简单线性酰胺骨架的结构上不同的实例Largazole和Psammaplin A的启发，我们通过用半刚性酰胺键取代Largazole中的烯烃部分，设计了一种新型分子杂合物。该杂合化合物已经由1-苹果酸分十步合成，总收率为7％。初步的生物学分析表明，用酰胺键取代反式烯烃部分将对HDAC的抑制作用产生不利影响。
• New building blocks for peptide and depsipeptide synthesis: hexafluoroacetone protected l-homoisoserine and d,l-homoisocysteine derivatives
  作者：Gábor Radics、Raul Pires、Beate Koksch、Salah M El-Kousy、Klaus Burger

  DOI：10.1016/s0040-4039(02)02712-0

  日期：2003.1

  syntheses of l-homoisoserine and d,l-homoisocysteine derivatives starting from l-malic and d,l-thiomalic acid using hexafluoroacetone as protecting and activating agent are described. The new compounds are interesting building blocks for the preparation of non-natural peptides and depsipeptides as well as for the construction of new GABA derivatives.

  描述了使用六氟丙酮作为保护剂和活化剂从l-苹果酸和d，l-硫代苹果酸开始的l-高丝氨酸和d，l-同型半胱氨酸衍生物的高效合成。新化合物是制备非天然肽和二肽肽以及构建新GABA衍生物的有趣构建基。
• Amide-to-Ester Substitution Allows Fine-Tuning of the Cyclopeptide Conformational Ensemble
  作者：Tommaso Cupido、Jan Spengler、Javier Ruiz-Rodriguez、Jaume Adan、Francesc Mitjans、Jaume Piulats、Fernando Albericio

  DOI：10.1002/anie.200907274

  日期：2010.4.1

  Without affecting the overall 3D structure, amide‐to‐ester backbone substitution (or ester scan) exerts a pronounced influence on the conformational equilibrium of the RGD cyclopeptide cilengitide and its derivatives (see figure; RGD=Arg‐Gly‐Asp). The appropriate substitution, which stabilized the receptor‐complementary conformations, improved the biological activity of this integrin antagonist.

  在不影响整体3D结构的情况下，酰胺至酯主链取代（或酯扫描）对RGD环肽cilengitide及其衍生物的构象平衡产生显着影响（见图； RGD = Arg-Gly-Asp）。适当的取代可稳定受体互补构象，从而改善了这种整合素拮抗剂的生物活性。
• A Novel Protecting/Activating Strategy for β-Hydroxy Acids and Its Use in Convergent Peptide Synthesis
  作者：Jan Spengler、Javier Ruíz-Rodríguez、Francesc Yraola、Miriam Royo、Manfred Winter、Klaus Burger、Fernando Albericio

  DOI：10.1021/jo7025788

  日期：2008.3.1

  β-Hydroxy acids were reacted with hexafluoroacetone and carbodiimides to give carboxy-activated six-membered lactones in good yields. On reaction with amines, the corresponding amides were obtained. We demonstrate the following applications of this protecting/activating strategy: preparation of carboxamides in solution and on solid phase (both normal and reverse mode); recovery and reuse of the excess

  β-羟基酸与六氟丙酮和碳二亚胺反应，以高收率得到羧基活化的六元内酯。与胺反应后，获得相应的酰胺。我们证明了这种保护/活化策略的以下应用：在溶液中和固相上（正向和反向模式）制备羧酰胺；固相合成中多余材料的回收和再利用；聚合固相肽合成（CSPPS），其肽段带有C端Ser或Thr，且差向异构化水平非常低（<1％，HPLC）。