((5S)-2,2-bis-(trifluoromethyl)-4-oxo-1,3-dioxolan-5-yl)-acetyl chloride | 172540-28-2

• 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)-acetyl chloride
• 英文别名: [(5S)-2,2-Bis(trifluoromethyl)-4-oxo-1,3-dioxolan-5-yl] acetyl chloride；2-[(4S)-5-oxo-2,2-bis(trifluoromethyl)-1,3-dioxolan-4-yl]acetyl chloride
• CAS: 172540-28-2
• 化学式: C₇H₃ClF₆O₄
• 分子量: 300.542
• InChiKey: ZKFGWHOTJFOCSJ-REOHCLBHSA-N

物化性质

• 沸点：
  254.2±35.0 °C(Predicted)
• 密度：
  1.688±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：
  52.6
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ((5S)-2,2-bis-(trifluoromethyl)-4-oxo-1,3-dioxolan-5-yl)-acetyl chloride 在 叠氮基三甲基硅烷 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 40.0h， 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：

  [(5S)-2,2-Bis(trifluoromethyl)-4-oxo-1,3-dioxolan-5-yl] acetic acid 在 氯化亚砜 作用下， 反应 10.0h， 生成 ((5S)-2,2-bis-(trifluoromethyl)-4-oxo-1,3-dioxolan-5-yl)-acetyl chloride
  参考文献：
  名称：

  由（S）-和（R）-苹果酸和（S）-和（R）-柠檬酸中的4,4-二氟-2-羟基丁酸的高效立体保守合成

  摘要：

  描述了使用六氟丙酮作为保护和活化剂的高手性4,4-二氟-2-羟基丁酸和4,4-二氟-2-羟基-2-甲基丁酸的制备简单立体保守性合成。

  DOI：

  10.1016/s0022-1139(99)00296-1

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。
• <b>Hexafluoroacetone as a Protecting and Activating Reagent: Synthesis of New Types of Fluoro-Substituted α-Amino, α-Hydroxy and α-Mercapto Acids</b>
  作者：Klaus Burger、Sergej Osipov、Torsten Lange、Pavel Tsouker、Jan Spengler、Lothar Hennig、Beate Koksch、Stefan Berger、Salah El-Kousy

  DOI：10.1055/s-2004-829131

  日期：——

  (S)-malic, (S)-citramalic and (S,R)-thiomalic acid, new types of 4,4-difluoro-substituted a-ami- no-, a-hydroxy- and a-mercaptopentanoic acids have been synthe- sized, applying hexafluoroacetone as protecting and activating reagent. The new partially fluorinated a-functionalized carboxylic acids represent interesting monomers for peptide and depsipeptide modification and for rational design and elucidation

  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。
• 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。
• A Preparatively Simple Access to Homochiral Heterocyclic α-Hydroxy Acids and their Derivatives
  作者：Klaus Burger、Elisabeth Windeisen、Elisabeth Heistracher、Torsten Lange、Abdel-Aleem H. Abdel-Aleem

  DOI：10.1007/s007060270005

  日期：2002.1

   The synthesis of homochiral heterocyclic α-hydroxy acids starting from ( S )- and ( R )-malic acid using hexafluoroacetone as protecting and activating agent is described. The new compounds are useful building blocks for peptide and depsipeptide modification.

  描述了使用六氟丙酮作为保护和活化剂 从（ S ）-和（ R ）-苹果酸开始合成手性杂环α-羟基酸 。新化合物是肽和二肽修饰的有用组成部分。
• Hexafluoroacetone as Protecting and Activating Reagent. Glycosylated Malic, Citramalic, and Thiomalic Acid Derivatives, New Glycosylated Building Blocks for Drug Design [1]
  作者：Christoph B�ttcher、Jan Spengler、Klaus Burger

  DOI：10.1007/s00706-004-0187-5

  日期：2004.10

  Glycosylated α-hydroxy and α-mercapto acids have been synthesized starting from malic/citramalic/thiomalic acid and Ac 4-β- D - Glc -NH2/ Bzl 4-β- D - Glc -NH2 using hexafluoroacetone as protecting and activating reagent.

  糖基化的α-羟基酸和α-巯基酸是从苹果酸/柠康酸/硫代苹果酸和 Ac 4- β- D - Glc -NH 2 / Bzl 4- β- D - Glc -NH 2出发， 以六氟丙酮为保护基并活化而合成的 试剂。