(S)-(-)-1-苄基-3-(叔丁氧羰基氨基)吡咯烷 | 131852-53-4

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-(-)-1-苄基-3-(叔丁氧羰基氨基)吡咯烷
• 中文别名: (S)-(-)-1-苄基-3-(boc-氨基)吡咯烷；(S)-(-)-1-苄基-3-(Boc-氨基)吡咯烷；(S)-1-苄基-3-N-Boc-吡咯烷；1-苄基-3-Boc-氨基-吡咯烷
• 英文名称: (S)-1-benzyl-3-(tert-butoxycarbonylamino)pyrrolidine
• 英文别名: tert-butyl (S)-(1-benzylpyrrolidine-3-yl)carbamate；tert-butyl (S)-(1-benzylpyrrolidin-3-yl)carbamate；(S)-1-benzyl-3-tert-butoxycarbonylaminopyrrolidine；1-N-benzyl-3(S)-(BOC-amino)-pyrrolidine；(S)-tert-Butyl (1-benzylpyrrolidin-3-yl)carbamate；tert-butyl N-[(3S)-1-benzylpyrrolidin-3-yl]carbamate
• CAS: 131852-53-4
• 化学式: C₁₆H₂₄N₂O₂
• 分子量: 276.379
• InChiKey: PHOIDJGLYWEUEK-AWEZNQCLSA-N

物化性质

• 熔点：
  77-81 °C(lit.)
• 沸点：
  385.1±31.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2933990090
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  存储条件：2-8℃，请保持干燥。

制备方法与用途

用途

(S)-(-)-1-苄基-3-(叔丁氧羰基氨基)吡咯烷主要应用于有机合成及化工医药的研发过程。

反应信息

• 作为反应物：
  描述：

  (S)-(-)-1-苄基-3-(叔丁氧羰基氨基)吡咯烷 在 5percent Pd/C 氢气 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 13.0h， 生成 (3S)-1-(2-adamantyl)pyrrolidin-3-amine
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Naphthamides as Dopamine D₃ Receptor Ligands

  摘要：

  A series of naphthamides were synthesized, and the affinities of these compounds were determined for dopamine D-2 and D-3 receptors using radioligand binding techniques. The naphthamide compounds that were prepared include N-(1-alkylpiperidin-4-yl)-4-bromo-1-methoxy-2-naphthamides (1-6), (S)-N-(1-alkylpyrrolidin-3-yl)-4-bromo-1-methoxy-2-naphthamides (7-12), (R)-N-(1-alkylpyrrolidin-3-yl)-4-bromo-1-methoxy-2-naphthamides (13-18), (S)-N-(1-alkyl-2-pyrrolidinylmethyl)-4-bromo-1-methoxy-2-naphthamides (19 -25), (R)-N-(1-alkyl-2-pyrrolidinylmethyl)-4-bromo-1-methoxy-2-naphthamides (26-31), and N-(9-alkyl-9-azabicyclo-[3.3.1]nonan-3 beta -yl)-4- bromo-1-methoxy-2-naphthamides (32, 33). The results of in vitro radioligand binding studies indicated that the majority of the naphthamide analogues bound with high affinity at both the D-2 and D-3 dopamine receptor subtypes and most of the compounds demonstrated some selectivity for the dopamine D-3 dopamine receptor subtype. These results demonstrated that both the structure of the central amine moiety (piperidine, pyrrolidine, and 9-azabicyclo[3.3.1]nonane) ring and the N-(alkyl) substitution on the amine significantly effects the binding affinity at D-2 and D-3 dopamine receptors. The bulkiness of the N-(1-alkyl) substituent was found to (a) have no effect on pharmacologic selectivity, (b) increase the affinity at Ds receptors, or (c) decrease the affinity at D-2 receptors. The most potent analogue in this series was (S)-N-(1-cycloheptylpyrrolidin-3-yl)-4-bromo-1-methoxy-2-naphthamide (10), which had equilibrium dissociation (K-i) values of 1.8 and 0.2 nM for D-2 and D-3 receptors, respectively. The most selective analogue was (R)-N-(1-cycloheptyl-2-pyrrolidinylmethyl)-4-bromo-1-methoxy-2-naphthamide (30), which had K-i values of 62.8 and 2.4 nM for D-2 and D-3 receptors, respectively. Radioligand binding results for sigma receptors indicated that the structure of the amine moiety and the N-(l-alkyl) substitutions also significantly influence the affinity and selectivity of these compounds at the sigma (1) and sigma (2) sigma receptor subtypes. The two naphthamides containing a 9-azabicyclo[3.3.1]nonan-3 beta -yl central ring were found to be selective for sigma (2) receptors.

  DOI：

  10.1021/jm0100077
• 作为产物：
  描述：

  BOC-L-天冬氨酸二甲酯 在 sodium tetrahydroborate 、 三乙胺 、 calcium chloride 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 (S)-(-)-1-苄基-3-(叔丁氧羰基氨基)吡咯烷
  参考文献：
  名称：

  手性 α-氨基酸向对映体纯 3-氨基环胺的有效转化

  摘要：

  摘要 对映异构纯的 3-氨基环胺，如 3-氨基吡咯烷、3-氨基哌啶和 2,3,4,5,6,7-六氢-1H-氮杂已从光学活性的天然α -氨基酸，例如 L-天冬氨酸、L-谷氨酸、L-2-氨基己二酸及其对映体。

  DOI：

  10.1080/00397919808004949

文献信息

• [EN] BENZENESULFONAMIDE COMPOUNDS AND THEIR USE AS THERAPEUTIC AGENTS<br/>[FR] COMPOSÉS BENZÈNESULFONAMIDES ET LEUR UTILISATION EN TANT QU'AGENTS THÉRAPEUTIQUES
  申请人：XENON PHARMACEUTICALS INC

  公开号：WO2017201468A1

  公开（公告）日：2017-11-23

  This invention is directed to benzenesulfonamide compounds, as stereoisomers, enantiomers, tautomers thereof or mixtures thereof; or pharmaceutically acceptable salts, solvates or prodrugs thereof, for the treatment of diseases or conditions associated with voltage-gated sodium channels, such as epilepsy.

  本发明涉及苯磺酰胺化合物，包括它们的立体异构体、对映异构体、互变异构体或其混合物；或用于治疗与电压门控钠通道相关的疾病或病症的药用可接受盐、溶剂化物或前药，例如癫痫。
• PROCESS FOR PRODUCING NITROGENOUS HETEROCYCLIC COMPOUND
  申请人：Toray Fine Chemicals Co., Ltd.

  公开号：EP1640364A1

  公开（公告）日：2006-03-29

  A nitrogenous heterocyclic compound such as 3-aminopyrrolidine derivative is produced by hydrogenolysis of an N-substituted nitrogenous heterocyclic compound with normal pressure hydrogen in a water-based solvent in presence of a catalyst. In the case an optically active 1-substituted-3-aminopyrrrolidine derivative is used as a raw material, an optically active 3-aminopyrrolidine derivative can be obtained as a product practically without racemination.

  通过在水基溶剂中，在催化剂的存在下，用常压氢对N-取代的氮杂环化合物进行氢解，可以制备氮杂环化合物，如3-氨基吡咯啉衍生物。如果使用具有光学活性的1-取代-3-氨基吡咯啉衍生物作为原料，则可以在实际上不经过消旋作用的情况下获得光学活性的3-氨基吡咯啉衍生物作为产物。
• 2-SUBSTITUTED-THIENOQUINOLONES AND RELATED COMPOUNDS AS ANTI-INFECTIVE AGENTS
  申请人：Phadke Avinash

  公开号：US20130165471A1

  公开（公告）日：2013-06-27

  Disclosed herein are 2-substituted-thienoquinolones and related compounds and their pharmaceutically acceptable salts useful as antiviral agents and having the general formula in which the variables R 2 , R 3 , and R 7 are defined herein. Certain compounds provided herein possess potent antibacterial, antiprotozoal, or antifungal activity and are particularly efficacious for the treatment of MRSA infections. The invention also provides pharmaceutical compositions, pharmaceutical compositions containing a 2-substituted-thienoquinolone in combination with one or more other active agent, and methods of treating microbial infections in animals by administering an effective amount of a 2-substituted-thienoquinolone to an animal suffering from a microbial infection.

  本文公开了2-取代噻吩喹啉及相关化合物和其药学上可接受的盐，作为抗病毒剂，并具有以下一般式中定义的变量R2，R3和R7。本文提供的某些化合物具有强大的抗菌、抗原虫或抗真菌活性，特别适用于治疗MRSA感染。本发明还提供了制药组合物，其中包含2-取代噻吩喹啉与一种或多种其他活性剂的组合物，以及通过向患有微生物感染的动物施用有效量的2-取代噻吩喹啉来治疗动物的微生物感染的方法。
• [EN] QUINOLIZINONE TYPE COMPOUNDS<br/>[FR] COMPOSES DU TYPE DE LA QUINOLIZINONE
  申请人：ABBOTT LABORATORIES

  公开号：WO1995010519A1

  公开（公告）日：1995-04-20

  (EN) Antibacterical coumpounds having formula (I) and the pharmaceutically acceptable salts, esters and amides thereof, preferred examples of which include those coumpounds wherein R1 is cycloalkyl of from three to eight carbon atoms or substituted phenyl; R2is selected from the group consisting of (a) halogen, (b) loweralkyl, (c) loweralkenyl, (d) cycloalkyl of from three to eight carbons, (e) cycloalkenyl of from four to eight carbons, (f) loweralkoxy, (g) aryloxy, (h) aryl(loweralkyl)oxy, (i) aryl(loweralkyl), (j) cycloalkyl(loweralkyl), (k) amino, (l) (loweralkyl)amino, (m) aryl(loweralkyl)amino, (n) hydroxy substituted (loweralkyl)amino, (o) phenyl, (p) substituted phenyl, (q) bicyclic nitrogen-containing heterocycle, (r) nitrogen-containingaromatic heterocycle, and (s) nitrogen-containing heterocycle having formula (Ia) where x is between zero and three; R3 is halogen; R4 is hydrogen, loweralkyl, a pharmaceutically acceptable cation, or a prodrug ester group; R5 is hydrogen, loweralkyl, halo(loweralkyl), or -NR13R14; and R6 is loweralkyl, as wellas pharmaceutical compositions containing such compounds and the use of the same in the treatment of bacterial infections.(FR) Composés antibactériens de la formule (I) et sels, esters et amides pharmaceutiquement acceptables de ceux-ci, dont des exemples préférés comprennent des composés dans lesquels: R1 est un cycloalcoyle avec deux à huit atomes de carbone ou un phényle substitué; R2 est sélectionné dans le groupe comprenant: (a) halogène, (b) alcoyle inférieur, (c) alcényle inférieur, (c) cycloalcoyle avec trois à huit atomes de carbone, (e) cycloalcényle avec quatre à huit atomes de carbone, (f) alcoxy inférieur, (g) aroyloxy, (h) aroyl(alcoyle inférieur)oxy, (I) aroyl(alcoyle inférieur), (j) cycloalcoyle(alcoyle inférieur), (k) amino, (l) (alcoyle inférieur)amino, (m) aroyl(alcoyle inférieur)amino, (n) (alcoyle inférieur)amino substitué par hydroxy, (o) phényle, (p) phényle substitué, (q) hétérocycle dicyclique azoté, (r) hétérocycle aromatique azoté et (s) hétérocycle azoté de la formule (Ia), dans laquelle R3 est un halogène; R4 est l'hydrogène, un alcoyle inférieur, un cation pharmaceutiquement acceptable ou un groupe ester promédicamenteux; R5 est l'hydrogène, un alcoyle inférieur, un halo(alcoyle inférieur) ou -NR13R14; et R6 est un alcoyle inférieur. L'invention décrit également des compositions pharmaceutiques contenant ces composés et l'utilisation de celles-ci dans le traitement des infections bactériennes.

  (中) 具有公式(I)及其药学上可接受的盐、酯和酰胺的抗菌化合物，其中R1是由三到八个碳原子的环烷基或取代的苯基; R2选自以下组中：(a)卤素，(b)较低的烷基，(c)较低的烯基，(d)由三到八个碳原子的环烷基，(e)由四到八个碳原子的环烯基，(f)较低的烷氧基，(g)芳氧基，(h)芳基(较低的烷氧基)，(i)芳基(较低的烷基)，(j)环烷基(较低的烷基)，(k)氨基，(l)(较低的烷基)氨基，(m)芳基(较低的烷基)氨基，(n)羟基取代的(较低的烷基)氨基，(o)苯基，(p)取代的苯基，(q)含氮的双环杂环，(r)含氮芳香杂环，(s)具有公式(Ia)的含氮杂环，其中x在零到三之间; R3是卤素; R4是氢、较低的烷基、药学上可接受的阳离子或前药酯基; R5是氢、较低的烷基、卤代(较低的烷基)或-NR13R14; R6是较低的烷基，以及包含这种化合物的药物组合物和在治疗细菌感染中使用它们的用途。
• Process for producing nitrogenous heterocyclic compound
  申请人：Morii Seiji

  公开号：US20060270847A1

  公开（公告）日：2006-11-30

  A nitrogenous heterocyclic compound such as 3-aminopyrrolidine derivative is produced by hydrogenolysis of an N-substituted nitrogenous heterocyclic compound with normal pressure hydrogen in a water-based solvent in presence of a catalyst. In the case an optically active 1-substituted-3-aminopyrrrolidine derivative is used as a raw material, an optically active 3-aminopyrrolidine derivative can be obtained as a product practically without racemination.

  一种含氮杂环化合物，例如3-氨基吡咯烷衍生物，通过在水基溶剂中，在催化剂存在下，用常压氢气对N-取代的含氮杂环化合物进行氢解反应制备而成。如果使用手性的1-取代-3-氨基吡咯烷衍生物作为原料，则可以实现无外消旋合成手性的3-氨基吡咯烷衍生物。