(2R,5S,2'R)-5-(2-acetoxy-3-butenyl)-5-(3-butenyl)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine | 210431-30-4

• 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,2'R)-5-(2-acetoxy-3-butenyl)-5-(3-butenyl)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine
• 英文别名: [(2R)-1-[(2R,5S)-5-but-3-enyl-3,6-dimethoxy-2-propan-2-yl-2H-pyrazin-5-yl]but-3-en-2-yl] acetate
• CAS: 210431-30-4
• 化学式: C₁₉H₃₀N₂O₄
• 分子量: 350.458
• InChiKey: SHYCBANGCGHRJV-FCEWJHQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  69.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,5S,2'R)-5-(2-acetoxy-3-butenyl)-5-(3-butenyl)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine 在 Grubbs catalyst first generation 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以93%的产率得到[(3R,6S,8R)-2,5-dimethoxy-3-propan-2-yl-1,4-diazaspiro[5.6]dodeca-1,4,9-trien-8-yl] acetate
  参考文献：
  名称：

  Ru(II)-catalyzed ring closing metathesis in stereoselective syntheses of constrained homoserine analogues

  摘要：

  Stereoselective syntheses of cyclic alpha-amipo-gamma-hydroxycyclohexene- and cycloheptene-alpha-carboxylic acids are described. RCM cyclization reactions were effected by Ru(II)-catalysis on sterically homogenous hydroxylated dienes. The diene substrates were available by stepwise, stereoselective alkylations of (R)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine with bromoalkenes, ethylene oxide and subsequent transformations. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00626-7
• 作为产物：
  描述：

  (2R,5S)-5-(3-butenyl)-2,5-dihydro-3,6-dimethoxy-5-(2-hydroxyethyl)-2-isopropylpyrazine 在 4-二甲氨基吡啶 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (2R,5S,2'R)-5-(2-acetoxy-3-butenyl)-5-(3-butenyl)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine
  参考文献：
  名称：

  Ru(II)-catalyzed ring closing metathesis in stereoselective syntheses of constrained homoserine analogues

  摘要：

  Stereoselective syntheses of cyclic alpha-amipo-gamma-hydroxycyclohexene- and cycloheptene-alpha-carboxylic acids are described. RCM cyclization reactions were effected by Ru(II)-catalysis on sterically homogenous hydroxylated dienes. The diene substrates were available by stepwise, stereoselective alkylations of (R)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine with bromoalkenes, ethylene oxide and subsequent transformations. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00626-7

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.
• Ru(II)-catalyzed ring closing metathesis in stereoselective syntheses of constrained homoserine analogues
  作者：Kristin Hammer、Christian Rømming、Kjell Undheim

  DOI：10.1016/s0040-4020(98)00626-7

  日期：1998.9

  Stereoselective syntheses of cyclic alpha-amipo-gamma-hydroxycyclohexene- and cycloheptene-alpha-carboxylic acids are described. RCM cyclization reactions were effected by Ru(II)-catalysis on sterically homogenous hydroxylated dienes. The diene substrates were available by stepwise, stereoselective alkylations of (R)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine with bromoalkenes, ethylene oxide and subsequent transformations. (C) 1998 Elsevier Science Ltd. All rights reserved.