(2R,5S)-5-(3-butenyl)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(2-propynyl)pyrazine | 194287-30-4

• 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)-5-(3-butenyl)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(2-propynyl)pyrazine
• 英文别名: (2R,5S)-5-but-3-enyl-3,6-dimethoxy-2-propan-2-yl-5-prop-2-ynyl-2H-pyrazine
• CAS: 194287-30-4
• 化学式: C₁₆H₂₄N₂O₂
• 分子量: 276.379
• InChiKey: SMOJEMSHHLBPHU-CZUORRHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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)-5-(3-butenyl)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(2-propynyl)pyrazine 在 4-二甲氨基吡啶 、 正丁基锂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2R,5S)-5-(4-acetoxy-2-butynyl)-5-(3-butenyl)-2,5-dihydro-3,6-dimethoxy-n-2-isopropylpyrazine
  参考文献：
  名称：

  Ruthenium-catalyzed enyne metathesis in stereoselective preparation of cyclic 1-amino-1-carboxylic acids

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(97)00671-6
• 作为产物：
  描述：

  3-溴丙炔 、 (2R,5S)-5-(But-3-enyl)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine 在 正丁基锂 作用下， 生成 (2R,5S)-5-(3-butenyl)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(2-propynyl)pyrazine
  参考文献：
  名称：

  Ruthenium-catalyzed enyne metathesis in stereoselective preparation of cyclic 1-amino-1-carboxylic acids

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(97)00671-6

文献信息

• [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.
• 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.