(S)-<2-<(2(R)-hydroxypropyl)amino>-1-methyl-2-oxoethyl>carbamic acid 1,1-dimethylethyl ester | 170568-60-2

• 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: (S)-<2-<(2(R)-hydroxypropyl)amino>-1-methyl-2-oxoethyl>carbamic acid 1,1-dimethylethyl ester
• 英文别名: (2R)-N-(N’-α-tert-butyloxycarbonyl-L-alanyl)-1-amino-2-propanol；tert-butyl N-[(2S)-1-[[(2R)-2-hydroxypropyl]amino]-1-oxopropan-2-yl]carbamate
• CAS: 170568-60-2
• 化学式: C₁₁H₂₂N₂O₄
• 分子量: 246.307
• InChiKey: QBYGMGDPOWAXSC-SFYZADRCSA-N

物化性质

• 沸点：
  441.2±30.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 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：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-<2-<(2(R)-hydroxypropyl)amino>-1-methyl-2-oxoethyl>carbamic acid 1,1-dimethylethyl ester 在 dimethyl sulfide borane 、 N,N-二异丙基乙胺 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 5-((3S,5S)-3,5-Dimethyl-piperazine-1-carbonyl)-7-trifluoromethyl-4,5-dihydro-imidazo[1,5-a]quinoxaline-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Piperazine Imidazo[1,5-a]quinoxaline Ureas as High-Affinity GABA_A Ligands of Dual Functionality

  摘要：

  A series of imidazo[1,5-alpha]quinoxaline piperazine ureas appended with a tert-butyl ester side chain at the 3-position was developed. Analogues within this series have high affinity for the gamma-aminobutyric acid A (GABA(A))/benzodiazepine receptor complex with efficacies ranging from inverse agonists to full agonists. Many analogues were found to be partial agonists as indicated by [S-35]TBPS and Cl- current ratios. Uniquely, a number of these analogues were found to have a bell-shaped dose-response profile in the alpha(1)beta(2)gamma(2) subtype as determined by whole cell patch-clamp technique, where in vitro efficacy was found to decrease with increasing drug concentration. Many of the compounds from this series were effective in antagonizing metrazole-induced seizures, consistent with anticonvulsant and possibly anxiolytic activity. Additionally, several analogues were also effective in lowering cGMP levels (to control values) after applied stress, also consistent with anxiolytic-like properties. The most effective compounds in these screens were also active in animal models of anxiety such as the Vogel and Geller assays. The use of the piperazine substituent allowed for excellent drug levels and a long duration of action in the central nervous system for many of the quinoxalines, as determined by ex vivo assay. Pharmacokinetic analysis of several compounds indicated excellent oral bioavailability and a reasonable half-life in rats. From this series emerged two partial agonists (55, 91) which had good activity in anxiolytic models, acceptable pharmacokinetics, and minimal benzodiazepine-type side effects.

  DOI：

  10.1021/jm9801307
• 作为产物：
  描述：

  Boc-L-丙氨酰胺 、 (R)-(+)-环氧丙烷 在 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 反应 14.5h， 以84.4%的产率得到(S)-<2-<(2(R)-hydroxypropyl)amino>-1-methyl-2-oxoethyl>carbamic acid 1,1-dimethylethyl ester
  参考文献：
  名称：

  一种2,6-二甲基哌嗪二盐酸盐的制备方法

  摘要：

  本发明提供了一种2,6‑二甲基哌嗪二盐酸盐的制备方法，所述制备方法以N‑Boc‑丙氨酰胺和环氧丙烷为原料，经过开环反应、基团保护反应、环化反应和还原反应后得到2,6‑二甲基哌嗪二盐酸盐。所述制备方法以L‑N‑Boc‑丙氨酰胺和R‑环氧丙烷为原料时，制备得到(2S,6S)‑2,6‑二甲基哌嗪二盐酸盐，以D‑N‑Boc‑丙氨酰胺和S‑环氧丙烷为原料时，制备得到(2R,6R)‑2,6‑二甲基哌嗪二盐酸盐。本发明提供的制备方法合成路线较短，且反应条件温和，适合工业化生产和应用。

  公开号：

  CN111646949B

文献信息

• Rhodium-Catalyzed Asymmetric Transfer Hydrogenation of Aryl Alkyl Ketones Employing Ligands Derived from Amino Acids
  作者：Jenny Wettergren、Alexey B. Zaitsev、Hans Adolfsson

  DOI：10.1002/adsc.200700345

  日期：2007.12.10

  The combination of (pentamethylcyclopentadienyl)rhodium dichloride dimer [RhCl2Cp*}2] and pseudodipeptide ligands, formed from N-Boc protected amino acids and amino alcohols, resulted in efficient and selective catalysts for the asymmetric transfer hydrogenation of ketones in 2-propanol. A number of different secondary alcohols was obtained in high yields and in excellent enantioselectivity using

  （五甲基环戊二烯基）二氯化铑二聚体[RhCl 2 Cp *} 2 ]和由N- Boc保护的氨基酸和氨基醇形成的假二肽配体的组合，导致了高效且选择性的催化剂，用于2-酮的不对称转移加氢丙醇。使用这些原位形成的催化剂，以高收率和优异的对映选择性获得了许多不同的仲醇。氘标记实验表明，氢化物转移反应是通过单氢途径发生的。
• Highly Enantioselective Ruthenium-Catalyzed Reduction of Ketones Employing Readily Available Peptide Ligands
  作者：Anders Bøgevig、Isidro M. Pastor、Hans Adolfsson

  DOI：10.1002/chem.200305553

  日期：2004.1.5

  Highly efficient and selective catalysts for the asymmetric reduction of aryl alkyl ketones under hydrogen-transfer conditions (2-propanol) were obtained by combining a novel class of pseudo-dipeptide ligands with [[RuCl(2)(p-cymene)](2)]. A library of 36 dipeptide-like ligands was prepared from N-Boc-protected alpha-amino acids and the enantiomers of 2-amino-1-phenylethanol and 1-amino-2-propanol

  通过将新型伪二肽配体与[[RuCl（2）（p-cymene）]（2 ）]。由N-Boc保护的α-氨基酸和2-氨基-1-苯基乙醇和1-氨基-2-丙醇的对映异构体制备了36种二肽样配体的文库。用苯乙酮的还原来评估催化剂库，并且用几种新型催化剂获得了1-苯基乙醇的优异对映选择性。发现基于N-Boc-L-丙氨酸和（S）-1-氨基-2-丙醇（配体A-（S）-4）的组合的配体特别有效。当该配体的原位形成的钌络合物用作各种芳基烷基酮的氢转移反应的催化剂时，
• Cyclic Carbo-Isosteric Depsipeptides and Peptides as a Novel Class of Peptidomimetics
  作者：Stéphanie M. Guéret、Peter Meier、Hans-Jörg Roth

  DOI：10.1021/ol5003797

  日期：2014.3.7

  A novel and highly efficient cyclization method has been developed to access a new class of cyclic carbo-isosteric depsipeptides and carbo-isosteric peptides. Our strategy requires easily accessible C-terminal methyl ketone ester or amide functionalized linear precursors as starting materials. The well-known reductive amination has then been used to afford cyclic tetra- to octa-pseudopeptides via a

  已经开发出一种新颖且高效的环化方法来获得新型的环状碳-等排的二肽和碳-等排的肽。我们的策略需要容易获得的C末端甲基酮酯或酰胺官能化的线性前体作为起始原料。众所周知的还原胺化已被用于通过在适度稀释下选择性地分子内形成甘氨酸拟肽单元来提供环状的四至八伪肽。
• EP0729469B1
  申请人：——

  公开号：EP0729469B1

  公开（公告）日：1998-09-23
• [EN] IMIDAZO[1,5-a]QUINOLINES FOR TREATMENT OF ANXIETY AND SLEEP DISORDERS<br/>[FR] IMIDAZO[1,5-a]QUINOLINES POUR LE TRAITEMENT DE L'ANXIETE ET DES TROUBLES DU SOMMEIL
  申请人：THE UPJOHN COMPANY

  公开号：WO1995014020A1

  公开（公告）日：1995-05-26

  (EN) Imidazo[1,5-a]quinolines of formula (I) which are useful pharmaceutical agents for the treatment of anxiety, sleep disorders, panic states, convulsions and muscle disorders.(FR) Imidazo[1,5-a]quinolines présentant la formule (I) qui sont des agents pharmaceutiques utiles dans le traitement de l'anxiété, des troubles du sommeil, des états de panique, des convulsions et des troubles musculaires.