N-tert-butoxycarbonyl-α-aminobutyric acid ethylamide | 187680-40-6

• 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: N-tert-butoxycarbonyl-α-aminobutyric acid ethylamide
• 英文别名: tert-butyl N-[(2S)-1-(ethylamino)-1-oxobutan-2-yl]carbamate
• CAS: 187680-40-6
• 化学式: C₁₁H₂₂N₂O₃
• 分子量: 230.307
• InChiKey: VFEAKMVOEWLNOB-QMMMGPOBSA-N

物化性质

• 沸点：
  387.4±25.0 °C(Predicted)
• 密度：
  1.006±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-α-aminobutyric acid ethylamide 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以90%的产率得到(S)-2-Amino-N-ethyl-butyramide; hydrochloride
  参考文献：
  名称：

  Specificity of Lysine:N6-Hydroxylase: A Hypothesis for a Reactive Substrate Intermediate in the Catalytic Mechanism

  摘要：

  The recombinant cytoplasmic preparation of lysine: N-6-hydroxlase catalyzes the conversion of L-lysine to its N-6-hydroxy derivative when supplemented with the cofactors NADPH and FAD. A number of lysine analogs reflecting minor alterations in the inherent structural features of the amino acid as well compounds with relatively high affinity for lysine binding domains in other proteins were examined for their ability to serve as substrates of lysine: N-6-hydroxylase. These studies have revealed that the enzyme does not tolerate any change in the structural features of L-lysine, its preferred substrate, with the exception of the replacement of the CgammaH2-methylene group by sulfur, as in (S)-2-aminoethyl-L-cysteine. L-Norleucine is a potent inhibitor of the enzyme while L-norvaline and L-alpha-aminobutyric acid do not exhibit such effect, indicating the importance of a C-4 hydrophobic side chain for effective interaction with the enzyme. Among the N-alkyl amides of hydrophobic amino acids, only L-norleucine methylamide and L-alpha-aminobutyric acid ethylamide serve as moderate inhibitors of lysine : N-6-hydroxylase. Based on the enzyme's stringent substrate specificity, a mechanism involving the conversion of L-lysine to 2-aminocaprolactam prior to its oxygenation by the 4a-peroxyflavin intermediate in the catalytic cycle is proposed. (C) 1996 Academic Press, Inc.

  DOI：

  10.1006/bioo.1996.0034
• 作为产物：
  描述：

  BOC-L-2-氨基丁酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.28h， 生成 N-tert-butoxycarbonyl-α-aminobutyric acid ethylamide
  参考文献：
  名称：

  Specificity of Lysine:N6-Hydroxylase: A Hypothesis for a Reactive Substrate Intermediate in the Catalytic Mechanism

  摘要：

  The recombinant cytoplasmic preparation of lysine: N-6-hydroxlase catalyzes the conversion of L-lysine to its N-6-hydroxy derivative when supplemented with the cofactors NADPH and FAD. A number of lysine analogs reflecting minor alterations in the inherent structural features of the amino acid as well compounds with relatively high affinity for lysine binding domains in other proteins were examined for their ability to serve as substrates of lysine: N-6-hydroxylase. These studies have revealed that the enzyme does not tolerate any change in the structural features of L-lysine, its preferred substrate, with the exception of the replacement of the CgammaH2-methylene group by sulfur, as in (S)-2-aminoethyl-L-cysteine. L-Norleucine is a potent inhibitor of the enzyme while L-norvaline and L-alpha-aminobutyric acid do not exhibit such effect, indicating the importance of a C-4 hydrophobic side chain for effective interaction with the enzyme. Among the N-alkyl amides of hydrophobic amino acids, only L-norleucine methylamide and L-alpha-aminobutyric acid ethylamide serve as moderate inhibitors of lysine : N-6-hydroxylase. Based on the enzyme's stringent substrate specificity, a mechanism involving the conversion of L-lysine to 2-aminocaprolactam prior to its oxygenation by the 4a-peroxyflavin intermediate in the catalytic cycle is proposed. (C) 1996 Academic Press, Inc.

  DOI：

  10.1006/bioo.1996.0034

文献信息

• Substituted 1,2-ethylenediamines, Methods for Preparing Them and Uses Thereof
  申请人：Eickmeier Christian

  公开号：US20060223759A1

  公开（公告）日：2006-10-05

  The present invention relates to substituted 1,2-ethylenediamines of general formula (I) wherein the groups R 1 to R 15 , A, B, L, i as well as X 1 -X 4 are defined as in the specification and claims and the use thereof for the treatment of Alzheimer's disease (AD) and similar diseases.

  本发明涉及通式（I）的取代1,2-乙二胺化合物，其中基团R1至R15，A，B，L，i以及X1-X4如规范和权利要求中所定义，并且其用于治疗阿尔茨海默病（AD）和类似疾病。
• Substituted Ethane-1,2-Diamines for the Treatment of Alzheimer's Disease II
  申请人：Peters Stefan

  公开号：US20080293680A1

  公开（公告）日：2008-11-27

  The invention relates to a compound of the formula (I), wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are defined as in the specification and claims and to its use for treating or preventing Alzheimer's disease and other similar diseases.
• SUBSTITUTED 1,2-ETHYLENEDIAMINES, METHODS FOR PREPARING THEM AND USES THEREOF
  申请人：EICKMEIER Christian

  公开号：US20100204160A1

  公开（公告）日：2010-08-12

  The present invention relates to substituted 1,2-ethylenediamines of general formula (I) wherein the groups R 1 to R 15 , A, B, L, i as well as X 1 -X 4 are defined as in the specification and claims and the use thereof for the treatment of Alzheimer's disease (AD) and similar diseases.
• US7713961B2
  申请人：——

  公开号：US7713961B2

  公开（公告）日：2010-05-11
• [EN] SUBSTITUTED ETHANE-1,2-DIAMINES FOR THE TREATMENT OF ALZHEIMER'S DISEASE II<br/>[FR] ETHANE-1,2-DIAMINES SUBSTITUES POUR LE TRAITEMENT DE LA MALADIE D'ALZHEIMER II
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2007014946A1

  公开（公告）日：2007-02-08

  [EN] The invention relates to a compound of the formula (I), wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are defined as in the specification and claims and to its use for treating or preventing Alzheimer's disease and other similar diseases.
  [FR] La présente invention concerne, d'une part un composé représenté par la formule (I), dans laquelle R¹, R², R³, R⁴, R⁵, R⁶, R⁷ et R⁸ sont tels que définis dans la spécification et les revendications, et d'autre part son utilisation pour le traitement ou la prévention de la maladie d'Alzheimer et d'autres maladies similaires.