(2R,5S)-5-allyl-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(2-propynyl)pyrazine | 194287-29-1

• 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-allyl-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(2-propynyl)pyrazine
• 英文别名: (2R,5S)-3,6-dimethoxy-2-propan-2-yl-5-prop-2-enyl-5-prop-2-ynyl-2H-pyrazine
• CAS: 194287-29-1
• 化学式: C₁₅H₂₂N₂O₂
• 分子量: 262.352
• InChiKey: QIWLMXOARYTTRH-IUODEOHRSA-N

物化性质

• 沸点：
  330.3±27.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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-allyl-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(2-propynyl)pyrazine 在 盐酸 作用下， 以 1,4-二氧六环 、 正己烷 为溶剂， 反应 6.5h， 生成 methyl (3S,5S)-3-amino-7-oxobicyclo[3.3.0]oct-8(1)-ene-3-carboxylate
  参考文献：
  名称：

  THE PAUSON-KHAND REACTION IN SYNTHESIS OF BICYCLIC RIGID α-AMINO ACIDS

  摘要：

  The combination of intramolecular Pauson-Khand methodology for Co-2(CO)(8) mediated cyclization, and the Scholkopf chiral auxiliary for stereoselective preparation of appropriate 1,6-heptenynes constitutes a powerful method for the preparation of rigidified bicyclic alpha -amino acids.

  DOI：

  10.1081/scc-100103996
• 作为产物：
  描述：

  3-溴丙炔 、 (2R,5S)-5-Allyl-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine 在 正丁基锂 作用下， 生成 (2R,5S)-5-allyl-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.
• THE PAUSON-KHAND REACTION IN SYNTHESIS OF BICYCLIC RIGID α-AMINO ACIDS
  作者：Jing Wang、Mette Lene Falck-Pedersen、Christian Rømming、Kjell Undheim

  DOI：10.1081/scc-100103996

  日期：2001.1.1

  The combination of intramolecular Pauson-Khand methodology for Co-2(CO)(8) mediated cyclization, and the Scholkopf chiral auxiliary for stereoselective preparation of appropriate 1,6-heptenynes constitutes a powerful method for the preparation of rigidified bicyclic alpha -amino acids.