(2R,5S)-2-isopropyl-3,6-dimethoxy-5-pent-4-en-1-yl-2,5-dihydropyrazine | 188177-80-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: (2R,5S)-2-isopropyl-3,6-dimethoxy-5-pent-4-en-1-yl-2,5-dihydropyrazine
• 英文别名: (2R,5S)-2-isopropyl-3,6-dimethoxy-5-(pent-4-enyl)-2,5-dihydropyrazine；(2S,5R)-3,6-dimethoxy-2-pent-4-enyl-5-propan-2-yl-2,5-dihydropyrazine
• CAS: 188177-80-2
• 化学式: C₁₄H₂₄N₂O₂
• 分子量: 252.357
• InChiKey: RLILSAGTZZCCCW-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  43.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,5S)-2-isopropyl-3,6-dimethoxy-5-pent-4-en-1-yl-2,5-dihydropyrazine 在 dirhodium tetraacetate 、 正丁基锂 、 对甲苯磺酰叠氮 、 copper chloride 、 水 、 氧气 、 三乙胺 、 六甲基二硅氮烷 、 palladium dichloride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 16.67h， 生成 (2'R,3S,5'R)-3-(5-isopropyl-3,6-dimethoxy-2-propyl-2,5-dihydropyrazin-2-yl)cyclopentan-1-one
  参考文献：
  名称：

  Rh(II)-carbenoid insertion into chiron substrates for stereoselective amino acid construction

  摘要：

  Chemoselective and regioselective rhodium(II)-carbenoid insertion reactions have been used for the stereoselective preparation of novel alpha-cyclopentyl-alpha-quaternary alpha-amino acid derivatives. Regio and stereochemistry have been established by X-ray analysis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.030
• 作为产物：
  描述：

  5-碘-1-戊烯 、 (R)-2,5-二氢-3,6-二甲氧基-2-异丙基吡嗪 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 (2R,5S)-2-isopropyl-3,6-dimethoxy-5-pent-4-en-1-yl-2,5-dihydropyrazine
  参考文献：
  名称：

  Novel potent apoA-I peptide mimetics that stimulate cholesterol efflux and pre-β particle formation in vitro

  摘要：

  Reverse cholesterol transport (RCT) is believed to be the primary mechanism by which HDL and its major protein apoA-I protect against atherosclerosis. Starting from the inactive 22-amino acid peptide representing the consensus sequence of the class A amphipathic helical repeats of apoA-I, we designed novel peptides able to mobilize cholesterol from macrophages in vitro, and to stimulate the formation of 'nascent HDL' particles, with potency comparable to the entire apoA-I protein. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.128

文献信息

• Ruthenium(II) in ring closing metathesis for the stereoselective preparation of cyclic 1-amino-1-carboxylic acids
  作者：Kristin Hammer、Kjell Undheim

  DOI：10.1016/s0040-4020(96)01132-5

  日期：1997.2

  Stereoselective synthesis of α-amino acids where the α-carbon of the amino acid is incorporated into a five-, six- or seven-membered ring is described. The stereoselective control results from stepwise bisalkenylation of (R)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine. Ring closing metathesis was effected by ruthenium(II)-catalysis. The spiro-cycloalkene intermediates were further transformed into

  描述了α-氨基酸的立体选择性合成，其中氨基酸的α-碳结合到五元，六元或七元环中。立体选择性对照是由（R）-2，5-二氢-3，6-二甲氧基-2-异丙基吡嗪的逐步双烯基化产生的。闭环易位是通过钌（II）催化实现的。螺环烯烃中间体进一步转化成1 -aminocycloalkene- 1个通过弱酸水解羧酸衍生物。
• Ruthenium-catalyzed enyne metathesis in stereoselective preparation of cyclic 1-amino-1-carboxylic acids
  作者：Kristin Hammer、Kjell Undheim

  DOI：10.1016/s0040-4020(97)00671-6

  日期：1997.7

  Stereoselective syntheses of alpha-amino acids are described. The alpha-carbon of the amino acid is incorporated into a five- or six-membered ring which is a conjugated diene with one exocyclic double bond. Enynes were intermediates for the metathesis cyclization reaction effected by ruthenium(II)-catalysis. The enyne substrates were available in stereochemically pure form by stepwise alkylations of the chiral auxiliary (R)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine with bromo-alkenes and -alkynes. (C) 1997 Elsevier Science Ltd.
• [EN] AMINO ACID COMPOUNDS<br/>[FR] COMPOSES AMINOACIDES
  申请人：UNDHEIM, Kjell

  公开号：WO1998030535A1

  公开（公告）日：1998-07-16

  (EN) This invention relates to amino-acid analogs, in particular to analogs which may be used in place of serine or threonine in the preparation of peptidic compounds. The analogs are compounds of formula (I) (where D is a bridging group which together with the carbon atom to which it is attached forms a substituted and/or saturated 4 to 10 membered carbocyclic ring) and stereoisomers, stereoisomer mixtures, salts, esters, amides and protected derivatives thereof.(FR) La présente invention concerne des analogues d'aminoacides, en particulier à des analogues pouvant être utilisés à la place de la sérine ou de la thréonine dans la préparation de composés peptidiques. Les analogues sont des composés de la formule (I) (dans laquelle D est un groupe formant un pont qui constitue avec l'atome de carbone auquel il est relié un composé carbocyclique saturé et/ou substitué ayant entre 4 et 10 chaînons). L'invention concerne en outre des stéréoisomères, des mélanges de stéréoisomères, des sels, des esters, des amides et des protégés dérivés desdits composés.
• Novel potent apoA-I peptide mimetics that stimulate cholesterol efflux and pre-β particle formation in vitro
  作者：Raffaele Ingenito、Charlotte Burton、Annunziata Langella、Xun Chen、Karolina Zytko、Antonello Pessi、Jun Wang、Elisabetta Bianchi

  DOI：10.1016/j.bmcl.2009.10.128

  日期：2010.1

  Reverse cholesterol transport (RCT) is believed to be the primary mechanism by which HDL and its major protein apoA-I protect against atherosclerosis. Starting from the inactive 22-amino acid peptide representing the consensus sequence of the class A amphipathic helical repeats of apoA-I, we designed novel peptides able to mobilize cholesterol from macrophages in vitro, and to stimulate the formation of 'nascent HDL' particles, with potency comparable to the entire apoA-I protein. (C) 2009 Elsevier Ltd. All rights reserved.
• Rh(II)-carbenoid insertion into chiron substrates for stereoselective amino acid construction
  作者：Mioara Andrei、Christian Römming、Kjell Undheim

  DOI：10.1016/j.tetasy.2004.07.030

  日期：2004.9

  Chemoselective and regioselective rhodium(II)-carbenoid insertion reactions have been used for the stereoselective preparation of novel alpha-cyclopentyl-alpha-quaternary alpha-amino acid derivatives. Regio and stereochemistry have been established by X-ray analysis. (C) 2004 Elsevier Ltd. All rights reserved.