4-isocyanatomethyl-2,2-bis(trifluoromethyl)-[1,3]oxathiolan-5-one | 170997-01-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 4-isocyanatomethyl-2,2-bis(trifluoromethyl)-[1,3]oxathiolan-5-one
• 英文别名: 4-(Isocyanatomethyl)-2,2-bis(trifluoromethyl)-1,3-oxathiolan-5-one
• CAS: 170997-01-0
• 化学式: C₇H₃F₆NO₃S
• 分子量: 295.162
• InChiKey: BSIAAMJOPQXQQI-UHFFFAOYSA-N

物化性质

• 沸点：
  321.9±42.0 °C(Predicted)
• 密度：
  1.72±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：
  81
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  9-芴甲醇 、 4-isocyanatomethyl-2,2-bis(trifluoromethyl)-[1,3]oxathiolan-5-one 以 氯仿 为溶剂， 以71%的产率得到(5-Oxo-2,2-bis-trifluoromethyl-[1,3]oxathiolan-4-ylmethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  硫代苹果酸合成DL-异半胱氨酸及其衍生物

  摘要：

  使用六氟丙酮作为保护和活化剂，将硫代马来酸转化为同型半胱氨酸。所获得的氨基甲酸酯5、6、7代表N-保护的，羧基活化的异半胱氨酸衍生物，非常适合进一步衍生化。

  DOI：

  10.1016/0040-4039(96)01837-0
• 作为产物：
  描述：

  [2,2-bis(trifluoromethyl)-5-oxo-1,3-oxathiolan-4-yl]acetic acid 在 氯化亚砜 、 叠氮基三甲基硅烷 作用下， 以 甲苯 为溶剂， 生成 4-isocyanatomethyl-2,2-bis(trifluoromethyl)-[1,3]oxathiolan-5-one
  参考文献：
  名称：

  硫代苹果酸合成DL-异半胱氨酸及其衍生物

  摘要：

  使用六氟丙酮作为保护和活化剂，将硫代马来酸转化为同型半胱氨酸。所获得的氨基甲酸酯5、6、7代表N-保护的，羧基活化的异半胱氨酸衍生物，非常适合进一步衍生化。

  DOI：

  10.1016/0040-4039(96)01837-0

文献信息

• Hexafluoroacetone as a Protecting and Activating Reagent. N- and O-Glycosylation of Isoserine and Isocysteine
  作者：Christoph B�ttcher、Jan Spengler、Lothar Hennig、Fernando Albericio、Klaus Burger

  DOI：10.1007/s00706-004-0248-9

  日期：2005.4

  Starting from HFA-protected malic and thiomalic acid a series of O- and N-glycoconjugates suitable for peptide and depsipeptide modification has been synthesized.
• Aggrecanase-2 inhibitors based on the acylthiosemicarbazide zinc-binding group
  作者：Lucie Maingot、Jamal Elbakali、Julie Dumont、Damien Bosc、Nicolas Cousaert、Agathe Urban、Gaelle Deglane、Bruno Villoutreix、Hideaki Nagase、Olivier Sperandio、Florence Leroux、Benoit Deprez、Rebecca Deprez-Poulain

  DOI：10.1016/j.ejmech.2013.08.027

  日期：2013.11

  Osteoarthritis is a disabling disease characterized by the articular cartilage breakdown. Aggrecanases are potential therapeutic targets for the treatment of this pathology. At the starting point of this project, an acylthiosemicarbazide was discovered to inhibit aggrecanase-2. The acylthiosemicarbazide Zn binding group is also a convenient linker for library synthesis. A focused library of 920 analogs was thus prepared and screened to establish structure-activity relationships. The modification of the acylthiosemicarbazide was also explored. This strategy combining library design and discrete compounds synthesis yielded inhibitor 35, that is highly selective for aggrecanases over a panel of metalloproteases and inhibits the degradation of native fully glycosylated aggrecan. A docking study generated binding conformations explaining the structure activity relationships. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Synthesis of DL-isocysteine and some derivatives from thiomalic acid
  作者：Raul Pires、Klaus Burger

  DOI：10.1016/0040-4039(96)01837-0

  日期：1996.11

  Thiomalic acid is transformed into isocysteine using hexafluoroacetone as protecting and activating agent. The urethanes 5, 6, 7 obtained represent N-protected, carboxylic group activated derivatives of isocysteine and are perfectly suited for further derivatizations.

  使用六氟丙酮作为保护和活化剂，将硫代马来酸转化为同型半胱氨酸。所获得的氨基甲酸酯5、6、7代表N-保护的，羧基活化的异半胱氨酸衍生物，非常适合进一步衍生化。