α-(Difluoromethyl)alanine, hydrochloride | 67654-64-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: α-(Difluoromethyl)alanine, hydrochloride
• 英文别名: (S)-(-)-2-difluoromethylalanine hydrochloride；α-difluoromethylalanin hydrochloride；2-Amino-3,3-difluoro-2-methylpropanoic acid hydrochloride；2-amino-3,3-difluoro-2-methylpropanoic acid;hydrochloride
• CAS: 67654-64-2
• 化学式: C₄H₇F₂NO₂*ClH
• 分子量: 175.563
• InChiKey: QUSSSNWYBQEOGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.48
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  63.3
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,3-Difluoro-2-<(2S)-2-methoxymethyl-1-pyrrolidinylmethyleneamino>-2-methylpropanoic acid, methyl ester 在 盐酸 作用下， 生成 α-(Difluoromethyl)alanine, hydrochloride
  参考文献：
  名称：

  Kolb, Michael; Barth, Jacqueline, Liebigs Annalen der Chemie, 1983, # 10, p. 1668 - 1688

  摘要：

  DOI：

文献信息

• Utilization of fluoroform for difluoromethylation in continuous flow: a concise synthesis of α-difluoromethyl-amino acids
  作者：Manuel Köckinger、Tanja Ciaglia、Michael Bersier、Paul Hanselmann、Bernhard Gutmann、C. Oliver Kappe

  DOI：10.1039/c7gc02913f

  日期：——

  be considered as an ideal reagent for difluoromethylation reactions. However, due to the low reactivity of fluoroform, only very few applications have been reported so far. Herein we report a continuous flow difluoromethylation protocol on sp3 carbons employing fluoroform as a reagent. The protocol is applicable for the direct Cα-difluoromethylation of protected α-amino acids, and enables a highly atom

  氟仿（CHF 3）被认为是二氟甲基化反应的理想试剂。然而，由于氟仿的低反应性，迄今为止仅报道了很少的应用。在本文中，我们报告了使用氟仿作为试剂在sp 3碳上连续流动的二氟甲基化方案。该协议是适用于直接Ç α保护的α氨基酸的-difluoromethylation，并且使活性药物成分依氟鸟氨酸的高度原子有效合成。
• Umpolung Reactivity of Difluoroenol Silyl Ethers with Amines and Amino Alcohols. Application to the Synthesis of Enantiopure α-Difluoromethyl Amines and Amino Acids
  作者：Florent Huguenot、Anne Billac、Thierry Brigaud、Charles Portella

  DOI：10.1021/jo702328v

  日期：2008.4.1

  Difluoroenol silyl ethers, produced in situ from acylsilanes and CF3TMS, react as electrophiles with amines to give difluoroimines, via the corresponding hemiaminal adduct, as evidenced by F-19 NMR spectroscopy. Reaction with (R)-phenylglycinol led to 2-difluoromethyloxazolidines. After separation of the diastereomers, reduction with LAH and Strecker-type synthesis gave enantiopure alpha-difluoromethy-lamines and alpha-difluoromethyl-alpha-amino acids, respectively.
• Kolb, Michael; Barth, Jacqueline, Liebigs Annalen der Chemie, 1983, # 10, p. 1668 - 1688
  作者：Kolb, Michael、Barth, Jacqueline

  DOI：——

  日期：——