(S)-N-methyl-1-phenyl-2-(pyrrolidin-1-yl)ethanamine | 116508-51-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-N-methyl-1-phenyl-2-(pyrrolidin-1-yl)ethanamine
• 英文别名: (1S)-N-methyl-1-phenyl-2-(pyrrolidin-1-yl)ethanamine；methyl-[1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl]-amine；(S)-N-methyl-1-phenyl-2-(1-pyrrolidinyl) ethanamine；(1S)-N-methyl-1-phenyl-2-pyrrolidin-1-ylethanamine
• CAS: 116508-51-1
• 化学式: C₁₃H₂₀N₂
• 分子量: 204.315
• InChiKey: ZINZYRWMDNKTBY-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-N-methyl-1-phenyl-2-(pyrrolidin-1-yl)ethanamine 在 硫酸 、 硝酸 、 镍 、 肼 作用下， 以 乙醇 为溶剂， 生成 N-[(1S)-1-(3-aminophenyl)-2-(pyrrolidin-1-yl)ethyl]-2-(3,4-dichlorophenyl)-N-methylacetamide
  参考文献：
  名称：

  2-（3,4-二氯苯基）-N-甲基-N-[（1S）-1-（3-异硫氰酸根合苯基）-2-（1-吡咯烷基）乙基]乙酰胺：产生选择性且长效的阿片受体亲和标记对小鼠的持久κ拮抗作用。

  摘要：

  DOI：

  10.1021/jm00037a001
• 作为产物：
  描述：

  (S)-(+)-扁桃酸 在 lithium aluminium tetrahydride 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 copper dichloride 作用下， 以 四氢呋喃 、 乙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 57.0h， 生成 (S)-N-methyl-1-phenyl-2-(pyrrolidin-1-yl)ethanamine
  参考文献：
  名称：

  Synthesis of chiral non-racemic 1,2-diamines from O-acetyl mandelic acid: application in enantioselective deprotonation of epoxides and diethylzinc addition to aldehydes

  摘要：

  A variety of 1,2-diamines were synthesized from readily available O-acetyl mandelic acid. These diamines were used in the synthesis of key intermediates for the preparation of (-)-utenone A and carbovir involving enantioselective deprotonation of epoxides, The addition of Et2Zn catalysed by some of these diamines was also studied and although ees were not high, some interesting observations were made in the outcome of the stereochemistry of the product. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00376-9
• 作为试剂：
  描述：

  cis-tert-butyldimethylsilyl (3,4-epoxycyclopentyl)methyl ether 在 正丁基锂 、 (S)-N-methyl-1-phenyl-2-(pyrrolidin-1-yl)ethanamine 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 48.0h， 生成 (1S,4R)-(+)-4-(tert-butyldimethylsilanyloxymethyl)cyclopent-2-enol 、 cis-(1R,4S)-4-tert-butyldimethylsilyloxymethyl-2-cyclopenten-1-ol
  参考文献：
  名称：

  Synthesis of chiral non-racemic 1,2-diamines from O-acetyl mandelic acid: application in enantioselective deprotonation of epoxides and diethylzinc addition to aldehydes

  摘要：

  A variety of 1,2-diamines were synthesized from readily available O-acetyl mandelic acid. These diamines were used in the synthesis of key intermediates for the preparation of (-)-utenone A and carbovir involving enantioselective deprotonation of epoxides, The addition of Et2Zn catalysed by some of these diamines was also studied and although ees were not high, some interesting observations were made in the outcome of the stereochemistry of the product. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00376-9

文献信息

• Enantioselective conjugate addition to cyclic enones with scalemic lithium organo(amido)cuprates, Part IV. Relationship between ligand structure and enantioselectivity
  作者：Bryant E. Rossiter、Masakatsu Eguchi、Guobin Miao、Nicole M. Swingle、Amelia E. Hernández、Denise Vickers、Ezdan Fluckiger、R. Greg Patterson、K. Vásavi Reddy

  DOI：10.1016/s0040-4020(01)86278-5

  日期：1993.1

  Scalemic lithium amides derived from primary and secondary amines react with organocopper compounds in ether or dimethyl sulfide to form lithium organo(amido)cuprates capable of enantioselective conjugate addition to 2-cycloalkenones. The most successful heterocuprate, in which the chiral ligand is (S)-N-methyl-1-phenyl-2-(1-piperidinyl)ethanamine, (S)-MAPP, 13, reacts with cyclic enones to form products

  衍生自伯胺和仲胺的垢性锂酰胺与有机铜化合物在醚或二甲基硫醚中反应，形成能够对2-环烯酮进行对映选择性共轭加成的有机（酰胺基）碳酸锂。最成功的杂铜酸盐，其中手性配体为（S）-N-甲基-1-苯基-2-（1-哌啶基）乙胺，（S） -MAPP，13，与环状烯酮反应生成最高97％ee。观察到由配体13形成的铜酸盐的非线性不对称诱导。
• .kappa. Opioid Receptor Selective Affinity Labels: Electrophilic Benzeneacetamides as .kappa.-Selective Opioid Antagonists
  作者：An-Chih Chang、Akira E. Takemori、William H. Ojala、William B. Gleason、Philip S. Portoghese

  DOI：10.1021/jm00052a008

  日期：1994.12

  high binding affinity and selectivity of the 3-isothiocyanate 3 (DIPPA) to kappa opioid receptors, wash studies have suggested that this involves covalent binding. In the mouse tail-flick assay, the 3- and 4-substituted isomers (3 and 5, respectively) produced long-lasting antagonism of the antinociceptive effect of the kappa opioid agonist, (+/-)-trans-2-(3,4-dichlorophenyl)-N-methyl-N-[2-(1-pyrrolidinyl)

  合成了2-（3,4-二氯苯基）-N-甲基-N- [1-（3-或4-取代的苯基）-2-（1-吡咯烷基）乙基]-乙酰胺3-6作为κ选择性亲和力标记并评估阿片样物质的活性。在平滑肌制剂中，非亲电子母体化合物（+）-S-2和亲和标记3-6表现为kappa激动剂，因为它们被norbinaltorphimine（norBNI）强烈拮抗。除了3-异硫氰酸酯3（DIPPA）对κ阿片受体的高结合亲和力和选择性外，洗涤研究还表明这涉及共价结合。在小鼠甩尾试验中，3-和4-取代的异构体（分别为3和5）对kappa阿片激动剂（+/-）-trans-2-（3 ，4-二氯苯基）-N-甲基-N- [2-（1-吡咯烷基）环己基]乙酰胺（（+/-）-U50，488）。相反，在甩尾试验中，非亲电子母体化合物（+）-S-2和富马酸酯衍生物4没有拮抗活性。在小鼠腹部拉伸试验中，DIPPA（3）和4-异硫氰酸酯5的剂量基本不同，也
• Sulfonylamino phenylacetamide derivatives and methods of their use
  申请人：——

  公开号：US20040254156A1

  公开（公告）日：2004-12-16

  Sulfonylamino phenylacetamide derivatives of the general formula 1 are disclosed. Pharmaceutical compositions containing the compounds and methods for their use are also disclosed. In certain embodiments, the compounds of the invention that, preferably: (1) bind with high affinity to &kgr; opioid receptors; (2) display good opioid receptor selectivity of &kgr; versus &mgr; and &kgr; versus &dgr;; and (3) do not substantially inhibit cytochrome P450 enzymatic activity, in particular CYP2D6, CYP2C9 and CYP3A4.

  揭示了通式1的磺酰氨基苯乙酰胺衍生物。还公开了含有这些化合物的药物组合物和它们的使用方法。在某些实施例中，本发明的化合物最好具有以下特征：(1) 与κ阿片受体结合的亲和力高；(2) 在κ与μ受体以及κ与δ受体之间显示良好的阿片受体选择性；以及(3) 不显著抑制细胞色素P450酶的活性，特别是CYP2D6、CYP2C9和CYP3A4。
• Structure activity studies related to 2-(3,4-dichlorophenyl)-N-methyl-N-[2-(1-pyrrolidinyl)-1-substituted-ethyl]acetamides: a novel series of potent and selective .kappa.-opioid agonists
  作者：Jeffrey J. Barlow、Thomas P. Blackburn、Gerard F. Costello、Roger James、David J. Le Count、Brian G. Main、Robert J. Pearce、Keith Russell、John S. Shaw

  DOI：10.1021/jm00115a001

  日期：1991.11

  optimum was found to be exemplified by 2-(3,4-dichlorophenyl)-N-methyl-N-[(1S)-1-(1-methylethyl)-2- (1-pyrrolidinyl)ethyl]acetamide (13). Subsequently, racemic or chiral amino acids were used to introduce other alkyl and aryl substituents at C1 of the ethyl linking moiety. A series of potent compounds, bearing substituted-aryl groups at C1, were discovered, typified by 2-(3,4-dichloro-phenyl)-N-methyl-N-[(1R

  本文描述了一系列N- [2-（1-吡咯烷基）乙基]乙酰胺及其相关类似物的合成，以及它们作为阿片样物质的生物学评价，这些酰胺在邻近酰胺氮（C1）的碳上被取代。激动剂。在研究的第一部分中，研究了当C1处的取代基为1-甲基乙基时，N-酰基，N-烷基和氨基官能团的变异体，并以2-（3,4-二氯苯基）为例进行了研究。 ）-N-甲基-N-[（1S）-1-（1-甲基乙基）-2-（1-吡咯烷基）乙基]乙酰胺（13）。随后，使用外消旋或手性氨基酸在乙基连接部分的C1处引入其他烷基和芳基取代基。发现了一系列在C1上带有取代芳基的有效化合物，其典型值为2-（3,4-二氯-苯基）-N-甲基-N-[（1R，
• 2-(3,4-Dichlorophenyl)-N-methyl-N-[2-(1-pyrrolidinyl)-1-substituted-ethyl]-acetamides: the use of conformational analysis in the development of a novel series of potent opioid .kappa. agonists
  作者：Gerard F. Costello、Roger James、John S. Shaw、Anthony M. Slater、Neil C. J. Stutchbury

  DOI：10.1021/jm00105a027

  日期：1991.1

  describes the synthesis of a series of N-[2-(1-pyrrolidinyl)ethyl]acetamides (1), methylated at C1 and/or C2 of the ethyl linking group, and their biological evaluation as opioid kappa agonists. Conformational analysis of corresponding desaryl analogues 2 suggested that only those compounds capable of occupying an energy minimum close to that of the known kappa agonist N-[2-(1-pyrrolidinyl)cyclohexyl]

  本文介绍了一系列在乙基连接基团的C1和/或C2处甲基化的N- [2-（1-吡咯烷基）乙基]乙酰胺（1）的合成及其作为阿片类κ激动剂的生物学评价。相应的脱芳基类似物2的构象分析表明，只有那些能占据最小能量接近已知的Kappa激动剂N- [2-（1-吡咯烷基）环己基]乙酰胺U-50488的化合物才可能具有Kappa激动剂性能。从手性氨基酸开始，在乙基连接部分的C1处引入了其他烷基和芳基取代基，得到的化合物能够采用与U-50488相同的构象。其中最有效的是2-（3,4-二氯苯基）-N-甲基-N-[（1S）-1-苯基-2-（1-吡咯烷基）乙基]乙酰胺（8），