(S)-<3,3,4,4,4-pentafluoro-1-(1-methylethyl)-2-oxobutyl>carbamic acid 1,1-dimethylethyl ester | 135836-64-5

• 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: (S)-<3,3,4,4,4-pentafluoro-1-(1-methylethyl)-2-oxobutyl>carbamic acid 1,1-dimethylethyl ester
• 英文别名: tert-butyl N-[(3S)-5,5,6,6,6-pentafluoro-2-methyl-4-oxohexan-3-yl]carbamate
• CAS: 135836-64-5
• 化学式: C₁₂H₁₈F₅NO₃
• 分子量: 319.272
• InChiKey: VYRBLIMTJCHZGK-ZETCQYMHSA-N

物化性质

• 沸点：
  294.7±40.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-<3,3,4,4,4-pentafluoro-1-(1-methylethyl)-2-oxobutyl>carbamic acid 1,1-dimethylethyl ester 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以96%的产率得到(S)-4-amino-1,1,1,2,2,-pentafluoro-5-methyl-3-hexanone hydrochloride
  参考文献：
  名称：

  Inhibition of Human Neutrophil Elastase with Peptidyl Electrophilic Ketones. 2. Orally Active PG-Val-Pro-Val Pentafluoroethyl Ketones

  摘要：

  Valylprolylvalyl pentafluoroethyl ketones with different N-protecting groups were evaluated in vitro and in vivo as inhibitors of human neutrophil elastase (HNE). Several of these compounds were found to be orally active in HNE-induced rat and hamster lung hemorrhage models. The compound with 4-(4-morpholinylcarbonyl)benzoyl as the protecting group, 71 (MDL 101,146), was studied in greater detail. Hydration and epimerization studies were performed on 71 and related compounds in various media, including human blood serum. Highperformance liquid chromatography studies on a reversed-phase system as a measure of the Lipophilicity of 71. and related compounds revealed a small range of relative retention times wherein the orally active compounds fell. The K-i value determined for 71 vs HNE was 25 nM.

  DOI：

  10.1021/jm00052a013
• 作为产物：
  描述：

  N-Boc-L-缬氨酸 在 N-甲基吗啉 、 methyllithium lithium bromide 、 氯甲酸异丁酯 作用下， 以 乙醚 为溶剂， 生成 (S)-<3,3,4,4,4-pentafluoro-1-(1-methylethyl)-2-oxobutyl>carbamic acid 1,1-dimethylethyl ester
  参考文献：
  名称：

  Efficient preparation of peptidyl pentaflouroethly ketones

  摘要：

  A concise method for the preparation of alpha-amino pentafluoroethyl ketone salts from amino acids is described. These intermediates are useful for the preparation of peptidyl pentafluoroethyl ketones.

  DOI：

  10.1016/s0040-4039(00)92063-x

文献信息

• Implementation of the Dakin-West reaction for the preparation of an α-amino-pentafluoroethyl ketone
  作者：Timothy T. Curran

  DOI：10.1016/0022-1139(95)03251-8

  日期：1995.9

  We have successfully implemented the Dakin-West reaction to prepare 4-(carbamoyl- or benzoylamino)-5-methyl-1,1,1,2,2-pentaffuorohexan-3-one (3, 7a and 7b). We also isolated and characterized the impurities obtained from this Dakin-West reaction. Although we were successful in the literature-described conversion of 3 to 4, we have been unsuccessful at benzamide cleavage of 7a or 7b under a variety

  我们已经成功地实施了达金-西反应来制备4-（氨基甲酰基或苯甲酰基氨基）-5-甲基- 1,1,1,2,2- pentaffuorohexan -3-酮（3，图7a和图7b）。我们还分离并表征了从该Dakin-West反应中获得的杂质。尽管我们成功地完成了文献中描述的3到4的转化，但由于各种亲电性的五氟乙基酮部分的存在，我们未能在多种条件下成功裂解7a或7b的苯甲酰胺。我们说明了5-五氟乙基恶唑15可以衍生自N-苯甲酰基-五氟乙基酮7a恶唑15也具有抗开环性。
• Efficient preparation of peptidyl pentaflouroethly ketones
  作者：Michael R. Angeloastro、Joseph P. Burkhart、Philippe Bey、Norton P. Peet

  DOI：10.1016/s0040-4039(00)92063-x

  日期：1992.6

  A concise method for the preparation of alpha-amino pentafluoroethyl ketone salts from amino acids is described. These intermediates are useful for the preparation of peptidyl pentafluoroethyl ketones.
• Inhibition of Human Neutrophil Elastase with Peptidyl Electrophilic Ketones. 2. Orally Active PG-Val-Pro-Val Pentafluoroethyl Ketones
  作者：Michael R. Angelastro、Larry E. Baugh、Philippe Bey、Joseph P. Burkhart、Teng-Man Chen、Sherrie L. Durham、C. Michelle Hare、Edward W. Huber、Michael J. Janusz

  DOI：10.1021/jm00052a013

  日期：1994.12

  Valylprolylvalyl pentafluoroethyl ketones with different N-protecting groups were evaluated in vitro and in vivo as inhibitors of human neutrophil elastase (HNE). Several of these compounds were found to be orally active in HNE-induced rat and hamster lung hemorrhage models. The compound with 4-(4-morpholinylcarbonyl)benzoyl as the protecting group, 71 (MDL 101,146), was studied in greater detail. Hydration and epimerization studies were performed on 71 and related compounds in various media, including human blood serum. Highperformance liquid chromatography studies on a reversed-phase system as a measure of the Lipophilicity of 71. and related compounds revealed a small range of relative retention times wherein the orally active compounds fell. The K-i value determined for 71 vs HNE was 25 nM.