(5R)-2-allyl-2,5-dihydro-3,6-dimethoxy-5-isopropylpyrazine | 190079-30-2

• 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: (5R)-2-allyl-2,5-dihydro-3,6-dimethoxy-5-isopropylpyrazine
• 英文别名: (5R)-2-allyl-3,6-dimethoxy-5-isopropyl-2,5-dihydropyrazine；(2R)-3,6-dimethoxy-2-propan-2-yl-5-prop-2-enyl-2,5-dihydropyrazine
• CAS: 190079-30-2
• 化学式: C₁₂H₂₀N₂O₂
• 分子量: 224.303
• InChiKey: HAHQBQXWZSNMSA-QVDQXJPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (5R)-2-allyl-2,5-dihydro-3,6-dimethoxy-5-isopropylpyrazine 在 4-二甲氨基吡啶 、 正丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 124.33h， 生成 methyl 2-acetamido-2-allylpent-4-enoate
  参考文献：
  名称：

  闭环复分解中的钌（II）用于立体选择性制备环状1-氨基-1-羧酸

  摘要：

  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。

  DOI：

  10.1016/s0040-4020(96)01132-5
• 作为产物：
  描述：

  (R)-2,5-二氢-3,6-二甲氧基-2-异丙基吡嗪 、 3-溴丙烯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到(5R)-2-allyl-2,5-dihydro-3,6-dimethoxy-5-isopropylpyrazine
  参考文献：
  名称：

  闭环复分解中的钌（II）用于立体选择性制备环状1-氨基-1-羧酸

  摘要：

  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。

  DOI：

  10.1016/s0040-4020(96)01132-5

文献信息

• DIPHENYL SULFIDE DERIVATIVES AND MEDICINES CONTAINING SAME AS ACTIVE INGREDIENT
  申请人：Kohno Yasushi

  公开号：US20120101068A1

  公开（公告）日：2012-04-26

  Provided are diphenyl sulfide derivatives which have excellent S1P3 antagonistic activity and are useful as drugs. Intensive studies have been made for the purpose of creating a compound having S1P3 antagonistic activity. As a result of the intensive studies, it has been found that diphenyl sulfide derivatives represented by general formula (1) have excellent S1P3 antagonistic activity. In general formula (1), R 1 is a hydrogen atom or the like; R 2 is an optionally substituted alkyl group having 1 to 6 carbon atoms, or the like; X is a methylene group which may be substituted with one or two fluorine atoms, or the like; Y is a hydrogen atom or the like; and Z is a halogen atom.

  提供了具有优异S1P3拮抗活性并且可用作药物的二苯基硫醚衍生物。为了创造具有S1P3拮抗活性的化合物，进行了深入研究。经过深入研究，发现由通式（1）表示的二苯基硫醚衍生物具有优异的S1P3拮抗活性。在通式（1）中，R1是氢原子或类似物；R2是具有1至6个碳原子的可选择取代的烷基基团或类似物；X是一个甲基基团，可能被一个或两个氟原子取代，或类似物；Y是氢原子或类似物；Z是卤素原子。
• DIPHENYL SULFIDE DERIVATIVE AND PHARMACEUTICAL PRODUCT WHICH CONTAINS SAME AS ACTIVE INGREDIENT
  申请人：Ishikawa Kumi

  公开号：US20130261089A1

  公开（公告）日：2013-10-03

  [Problem] To provide a diphenyl sulfide derivative which is useful as a pharmaceutical product that has excellent S1P3 antagonist activity. [Solution] The inventors have discovered that a diphenyl sulfide derivative represented by general formula (1) (wherein R1 represents an alkoxy group having 1-6 carbon atoms, R2 represents a propyl group or an allyl group, X represents methylene or an oxygen atom, and Z represents a halogen atom) has excellent S1P3 antagonist activity as a result of extensive researches for the production of a compound that has S1P3 antagonist activity.

  提供一种二苯硫醚衍生物，作为一种具有优异S1P3拮抗活性的药用产品。发明者发现，通过对具有S1P3拮抗活性的化合物的生产进行广泛研究，一种由通式（1）表示的二苯硫醚衍生物（其中R1代表具有1-6个碳原子的烷氧基，R2代表丙基基团或烯丙基团，X代表亚甲基或氧原子，Z代表卤素原子）具有优异的S1P3拮抗活性。
• Synthesis of conformationally restricted serine derivatives through ruthenium(II)-catalyzed ring closing metathesis
  作者：Kristin Hammer、Kjell Undheim

  DOI：10.1016/s0040-4020(97)00252-4

  日期：1997.4

  Stereoselective synthesis of α-amino-β-hydroxy acids where the α-carbon of the amino acid is incorporated into a five-, six- or seven-membered ring is described. The stereoselective control at the chiral auxiliary carbon results from stepwise alkenylation and aldol formation using metalated species of the chiral auxiliary (R)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine. Ring closing metathesis was

  描述了α-氨基-β-羟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。在手性辅助碳上的立体选择性控制是通过使用手性辅助（R）-2,5-二氢-3,6-二甲氧基-2-异丙基吡嗪的金属化物质逐步进行烯基化和羟醛形成而产生的。闭环易位是通过钌（II）催化实现的。通过温和的酸水解将螺-环烯烃中间体转化为1-氨基-2-羟基环烯烃-1-羧酸衍生物。
• Diphenyl sulfide derivative and pharmaceutical product which contains same as active ingredient
  申请人：Ishikawa Kumi

  公开号：US08993543B2

  公开（公告）日：2015-03-31

  [Problem] To provide a diphenyl sulfide derivative which is useful as a pharmaceutical product that has excellent S1P3 antagonist activity. [Solution] The inventors have discovered that a diphenyl sulfide derivative represented by general formula (1) (wherein R1 represents an alkoxy group having 1-6 carbon atoms, R2 represents a propyl group or an allyl group, X represents methylene or an oxygen atom, and Z represents a halogen atom) has excellent S1P3 antagonist activity as a result of extensive researches for the production of a compound that has S1P3 antagonist activity.

  [问题] 提供一种二苯基硫醚衍生物，该衍生物可用作具有优异S1P3拮抗活性的药物产品。[解决方案] 发明人已经发现，一种由通式（1）表示的二苯基硫醚衍生物（其中R1代表具有1-6个碳原子的烷氧基，R2代表丙基基团或烯丙基基团，X代表亚甲基或氧原子，Z代表卤素原子）具有优异的S1P3拮抗活性，这是对具有S1P3拮抗活性的化合物进行广泛研究的结果。
• A stereoselective synthesis of a spiro-bridged bis(α-amino acid) derivative based on Ru(II)-catalysed RCM reactions
  作者：Mioara Andrei、Jon Efskind、Kjell Undheim

  DOI：10.1016/j.tet.2007.03.008

  日期：2007.5

  Methodology for a stereoselective synthesis of a member of a novel family of spiro-bridged bis(a-amino acid) derivatives is described. The key step in the construction is a spirane annulation reaction effected by a Ru(Il)-catalysed ring-closing metathesis (RCM) reaction of an appropriately substituted tetraene. The latter became available after stereocontrolled allylations of 3,3-bis[2-((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)ethyl]-1,4-pentadiene, which was prepared in several reaction steps from (2R)-2,5-dihydro-2isopropyl-3,6-dimethoxypyrazine as a chiral starting material. (C) 2007 Elsevier Ltd. All rights reserved.