sodium (R)-[2-²H₁]-fluoroacetate | 1447204-39-8

• 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: sodium (R)-[2-²H₁]-fluoroacetate
• 英文别名: sodium;(2R)-2-deuterio-2-fluoroacetate
• CAS: 1447204-39-8
• 化学式: C₂H₂FO₂*Na
• 分子量: 101.017
• InChiKey: JGFYQVQAXANWJU-XTOJGXFPSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -4.29
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  sodium (R)-[2-²H₁]-fluoroacetate 、 正己醇 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以66%的产率得到n-hexyl (R)-[1-²H₁]-fluoroacetate
  参考文献：
  名称：

  Chiral fluoroacetic acid: synthesis of (R)- and (S)-[2H1]-fluoroacetate in high enantiopurity

  摘要：

  A two-step synthesis of (R)- and (S)-[H-2(1)]-fluoroacetate (sodium salts) in high enantioselectivity is reported. The synthesis is the development of a previous one in which the enantioselectivity has been increased from similar to 38% ee to >95% ee. The improvement in enantioselectivity applied Bio's methodology, which involved a deoxyfluorination reaction with DAST on either enantiomer of [H-2(1)]-benzyl alcohol, adding TMS-morpholine to the reaction. The additive promotes an S(N)2 inversion process, and suppresses a competing non-stereospecific S(N)1 reaction course, and as a result significantly improves the stereointegrity of the C-F bond formation. The intermediate [H-2(1)]-benzyl alcohols, [H-2(1)]-benzyl fluorides and the product [H-2(1)]-fluoroacetates as their hexyl esters were separately assayed for their stereochemical integrity, using the Courtieu method. This method involved measuring their H-2 NMR spectra in a chiral matrix of poly-gamma-benzyl L-glutamate. The chiral assay demonstrated that there was no significant loss in stereointegrity during the deoxyfluorination reaction and showed that the enantiomers of [H-2(1)]-fluoroacetate were generated with high enantiomeric purity (95% ee). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.05.001
• 作为产物：
  描述：

  (R)-7-[²H₁]-benzyl fluoride 在 sodium periodate 、 ruthenium(III) trichloride hydrate 、 sodium hydroxide 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 48.0h， 以17%的产率得到sodium (R)-[2-²H₁]-fluoroacetate
  参考文献：
  名称：

  Chiral fluoroacetic acid: synthesis of (R)- and (S)-[2H1]-fluoroacetate in high enantiopurity

  摘要：

  A two-step synthesis of (R)- and (S)-[H-2(1)]-fluoroacetate (sodium salts) in high enantioselectivity is reported. The synthesis is the development of a previous one in which the enantioselectivity has been increased from similar to 38% ee to >95% ee. The improvement in enantioselectivity applied Bio's methodology, which involved a deoxyfluorination reaction with DAST on either enantiomer of [H-2(1)]-benzyl alcohol, adding TMS-morpholine to the reaction. The additive promotes an S(N)2 inversion process, and suppresses a competing non-stereospecific S(N)1 reaction course, and as a result significantly improves the stereointegrity of the C-F bond formation. The intermediate [H-2(1)]-benzyl alcohols, [H-2(1)]-benzyl fluorides and the product [H-2(1)]-fluoroacetates as their hexyl esters were separately assayed for their stereochemical integrity, using the Courtieu method. This method involved measuring their H-2 NMR spectra in a chiral matrix of poly-gamma-benzyl L-glutamate. The chiral assay demonstrated that there was no significant loss in stereointegrity during the deoxyfluorination reaction and showed that the enantiomers of [H-2(1)]-fluoroacetate were generated with high enantiomeric purity (95% ee). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.05.001

文献信息

• Chiral fluoroacetic acid: synthesis of (R)- and (S)-[2H1]-fluoroacetate in high enantiopurity
  作者：Rudy D.P. Wadoux、Xiaowei Lin、Neil S. Keddie、David O’Hagan

  DOI：10.1016/j.tetasy.2013.05.001

  日期：2013.6

  A two-step synthesis of (R)- and (S)-[H-2(1)]-fluoroacetate (sodium salts) in high enantioselectivity is reported. The synthesis is the development of a previous one in which the enantioselectivity has been increased from similar to 38% ee to >95% ee. The improvement in enantioselectivity applied Bio's methodology, which involved a deoxyfluorination reaction with DAST on either enantiomer of [H-2(1)]-benzyl alcohol, adding TMS-morpholine to the reaction. The additive promotes an S(N)2 inversion process, and suppresses a competing non-stereospecific S(N)1 reaction course, and as a result significantly improves the stereointegrity of the C-F bond formation. The intermediate [H-2(1)]-benzyl alcohols, [H-2(1)]-benzyl fluorides and the product [H-2(1)]-fluoroacetates as their hexyl esters were separately assayed for their stereochemical integrity, using the Courtieu method. This method involved measuring their H-2 NMR spectra in a chiral matrix of poly-gamma-benzyl L-glutamate. The chiral assay demonstrated that there was no significant loss in stereointegrity during the deoxyfluorination reaction and showed that the enantiomers of [H-2(1)]-fluoroacetate were generated with high enantiomeric purity (95% ee). (C) 2013 Elsevier Ltd. All rights reserved.