2-碘-3-甲氧基吡嗪 | 58139-04-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2-碘-3-甲氧基吡嗪
• 英文名称: 2-iodo-3-methoxypyrazine
• CAS: 58139-04-1
• 化学式: C₅H₅IN₂O
• 分子量: 236.012
• InChiKey: PDMRYBKGSOJHJJ-UHFFFAOYSA-N

物化性质

• 熔点：
  62℃
• 沸点：
  259℃
• 密度：
  1.935
• 闪点：
  110℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  2-甲氧基吡嗪	2-methoxypyrazine	3149-28-8	C5H6N2O	110.115

反应信息

• 作为反应物：
  描述：

  2-碘-3-甲氧基吡嗪 在 异丙基氯化镁 作用下， 以 四氢呋喃 为溶剂， 反应 0.12h， 生成 (3-methoxypyrazin-2-yl)magnesium chloride
  参考文献：
  名称：

  Towards a biomimetic synthesis of schischkiniin: assembling the bis-dihydropyrazinone cycloaddition precursor

  摘要：

  The final step in the biosynthesis of the natural product schischkiniin is proposed to be a photochemically driven [2+2]-cycloaddition between two dihydropyrazinone units tethered to a 1,1 '-bisindole. Herein, we describe the extensive efforts aimed at synthesizing the cycloaddition precursor 2, which has been obtained as its di-Boc protected derivative 30. Two bidirectional approaches were examined, both starting with the diallylated hydrazobenzene 19 undergoing two simultaneous intramolecular Heck cyclizations to give 3,3 '-dimethylene-1,1 '-bisindoline (20), which was readily converted to the 1,1 '-bisindole-3,3 '-dicarbaldehyde (14) by a bromination hydrolysis oxidation sequence. In the initial approach, the simultaneous addition of the pyrazinyl Grignard 15 to dicarbaldehyde 14 followed by reduction and demethylation was successful, but the imines in the resulting bis-pyrazinone 5 could not be selectively reduced to the cycloaddition precursor 2. A revised route involving simultaneous Horner-Wadsworth-Emmons reactions between dicarbaldehyde 14 and phosphonoglycine 23 followed by reduction gave 1,1 '-bistryptophan 25, which underwent two consecutive thermally driven amidations to the bisamide 27. Acid-mediated cyclization of 27 gave the di-Boc protected cycloaddition precursor 30, from which the Boc groups could not be removed under a variety of conditions. These results provide a platform for an eventual biomimetic synthesis of 1, as well as demonstrating that 1,1 '-bisindoles are sturdy heterocyclic motifs capable of surviving lengthy synthetic sequences. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.081
• 作为产物：
  描述：

  2-甲氧基吡嗪 在 2,2,6,6-四甲基哌啶 、 正丁基锂 、 cadmium(II) chloride-N,N,N',N'-tetramethylethylenediamine 、 碘 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以47%的产率得到2-碘-3-甲氧基吡嗪
  参考文献：
  名称：

  使用混合的锂-镉，锂-铟和锂-锌物种的功能化芳香剂的去质子化金属化

  摘要：

  在CDCl原位混合物2 ⋅TMEDA;（0.5当量TMEDA = Ñ，Ñ，N' ，N'四甲基乙二胺）或的InCl 3与[李（TMP）]（TMP = 2,2,6,6（0.33当量） -tetramethylpiperidino;分别为1.5或1.3当量，）与氯化锌的前述混合物进行了比较2 ⋅TMEDA（0.5当量），用于他们的能力去质子苯甲醚，苯并噻唑，和嘧啶和[李（TMP）]（1.5当量）。[（tmp）3当在室温下用于四氢呋喃中时，CdLi]被证明是最好的碱，随后用碘进行捕集证明了这一点。然后证明了Cd-Li碱适用于多种芳族化合物的金属化，包括带有反应性官能团的苯（CONEt 2，CO 2 Me，CN，COPh）或重卤素（Br，I）和杂环（来自呋喃） ，噻吩，吡咯，恶唑，噻唑，吡啶和二嗪系列）。得益于双重激活位置的五元杂环在室温下也被双去质子化。由此获得的芳族碳酸钙可参与钯催化的交叉偶联反应，或简单地用酰氯淬灭。

  DOI：

  10.1002/chem.200901432

文献信息

• [EN] OXADIAZOLYLTHIOPHENE DERIVATIVES USEFUL AS HISTONE DEACETYLASE INHIBITORS<br/>[FR] DÉRIVÉS D'OXADIAZOLYLTHIOPHÈNE À UTILISER EN TANT QU'INHIBITEURS DE L'HISTONE DÉSACÉTYLASE
  申请人：KARUS THERAPEUTICS LTD

  公开号：WO2019166824A1

  公开（公告）日：2019-09-06

  A compound of Formula I : (I) or a pharmaceutically acceptable salt thereof, wherein: each R' is QR1; each Q is independently selected from a bond, -C1-C10 alkylene, -C2-C10 alkenylene, -C(O)-, -C(O)O-, -C(O)N(R1)-, -C(O)N(R1)SO2- -N(R1)C(O)-, - N(R1)-, -N(SO2(R1)), -N(R1)SO2- -C(O)NR4R5-, -N(R4R5)C(O)-, -N(R4R5)- - S-, -SO-, -SO2-, -S(O)O-, -SO2N(R1)- and -O-; each R1 is independently selected from H, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C1-C10 haloalkyl, C1-C10 heteroalkyl, aryl, heteroaryl, C3-C10 cycloalkyl, -(C1-C10 alkylene)-C3-C10 cycloalkyl, halogen, cyano, C1-C10 alkylene- aryl, C1-C10 alkylene heteroaryl, C1-C10 heterocycloalkyl and -(C1-C10 alkylene)- C1-C10 heterocycloalkyl. The compounds are inhibitors of HDAC and therefore have potential utility in the therapy of a number of conditions including cancer and inflammation.

  一种Formula I的化合物：(I)或其药学上可接受的盐，其中：每个R'是QR1；每个Q独立地选自键，-C1-C10烷基，-C2-C10烯基，-C(O)-，-C(O)O-，-C(O)N(R1)-，-C(O)N(R1)SO2-，-N(R1)C(O)-，-N(R1)-，-N(SO2(R1))，-N(R1)SO2-，-C(O)NR4R5-，-N(R4R5)C(O)-，-N(R4R5)-，-S-，-SO-，-SO2-，-S(O)O-，-SO2N(R1)-和-O-；每个R1独立地选自H，C1-C10烷基，C2-C10烯基，C2-C10炔基，C1-C10卤代烷基，C1-C10杂原子烷基，芳基，杂芳基，C3-C10环烷基，-(C1-C10烷基)-C3-C10环烷基，卤素，氰基，C1-C10烷基-芳基，C1-C10烷基-杂原子芳基，C1-C10杂环烷基和-(C1-C10烷基)-C1-C10杂环烷基。这些化合物是HDAC的抑制剂，因此在治疗包括癌症和炎症在内的多种疾病中具有潜在用途。
• [EN] AKT / PKB INHIBITORS<br/>[FR] INHIBITEURS D'AKT/PKB
  申请人：ALMAC DISCOVERY LTD

  公开号：WO2011055115A1

  公开（公告）日：2011-05-12

  The invention relates to a series of compounds with particular activity as inhibitors of the serine-threonine kinase AKT. Also provided are pharmaceutical compositions comprising same as well as methods for treating cancer.

  这项发明涉及一系列具有特定活性的化合物，作为丝氨酸-苏氨酸激酶AKT的抑制剂。还提供了包含这些化合物的药物组合物，以及治疗癌症的方法。
• [EN] 5-(3-AMINOPHENYL)-5-ALKYL-5,6-DIHYDRO-2H-[1,4]OXAZIN-3-AMINE DERIVATIVES<br/>[FR] DÉRIVÉS DE 5-(3-AMINOPHÉNYL)-5-ALKYL-5,6-DIHYDRO-2H-[1,4]OXAZIN-3-AMINE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2013083556A1

  公开（公告）日：2013-06-13

  The present invention relates to novel 5-(3-aminophenyl)-5-alkyl-5,6-dihydro- 2H-[1,4]oxazin-3-amine derivatives as inhibitors of beta-secretase, also known as beta- site amyloid cleaving enzyme, BACE, BACE 1, Asp2, or memapsin2. The invention is also directed to pharmaceutical compositions comprising such compounds, to processes for preparing such compounds and compositions, and to the use of such compounds and compositions for the prevention and treatment of disorders in which beta-secretase is involved, such as Alzheimer's disease (AD), mild cognitive impairment, senility, dementia, dementia with Lewy bodies, cerebral amyloid angiopathy, multi-infarct dementia, Down's syndrome, dementia associated with stroke, dementia associated with Parkinson's disease and dementia associated with beta-amyloid. (Formula I)

  本发明涉及一种新型的5-(3-氨基苯基)-5-烷基-5,6-二氢-2H-[1,4]噁嗪-3-胺衍生物，作为β-分泌酶抑制剂，也被称为β-位点淀粉样蛋白裂解酶、BACE、BACE 1、Asp2或memapsin2。该发明还涉及包含这些化合物的药物组合物，用于制备这些化合物和组合物的工艺，以及利用这些化合物和组合物预防和治疗涉及β-分泌酶的疾病，如阿尔茨海默病（AD）、轻度认知障碍、老年痴呆、带有Lewy小体的痴呆、脑淀粉样脉管病、多梗塞性痴呆、唐氏综合征、与中风相关的痴呆、与帕金森病相关的痴呆以及与β-淀粉样蛋白相关的痴呆等疾病的治疗和预防。（化学式I）
• 5-(3-AMINOPHENYL)-5-ALKYL-5,6-DIHYDRO-2H-[1,4]OXAZIN-3-AMINE DERIVATIVES
  申请人：Janssen Pharmaceutica NV

  公开号：US20140364428A1

  公开（公告）日：2014-12-11

  The present invention relates to novel 5-(3-aminophenyl)-5-alkyl-5,6-dihydro-2H-[1,4]oxazin-3-amine derivatives as inhibitors of beta-secretase, also known as beta-site amyloid cleaving enzyme, BACE, BACE1, Asp2, or memapsin2. The invention is also directed to pharmaceutical compositions comprising such compounds, to processes for preparing such compounds and compositions, and to the use of such compounds and compositions for the prevention and treatment of disorders in which beta-secretase is involved, such as Alzheimer's disease (AD), mild cognitive impairment, senility, dementia, dementia with Lewy bodies, cerebral amyloid angiopathy, multi-infarct dementia, Down's syndrome, dementia associated with stroke, dementia associated with Parkinson's disease and dementia associated with beta-amyloid.

  本发明涉及一种新型5-(3-氨基苯基)-5-烷基-5,6-二氢-2H-[1,4]噁嗪-3-胺衍生物，作为β-分泌酶抑制剂，也被称为β-位点淀粉样蛋白裂解酶、BACE、BACE1、Asp2或memapsin2。该发明还涉及包含这些化合物的药物组合物，用于制备这些化合物和组合物的方法，以及将这些化合物和组合物用于预防和治疗涉及β-分泌酶的疾病，如阿尔茨海默病（AD）、轻度认知障碍、老年痴呆、带有Lewy小体的痴呆、脑淀粉样血管病、多发性梗塞性痴呆、唐氏综合征、中风相关的痴呆、帕金森病相关的痴呆和β-淀粉样蛋白相关的痴呆。
• AKT / PKB INHIBITORS
  申请人：Bell Mark Peter

  公开号：US20120309739A1

  公开（公告）日：2012-12-06

  The invention relates to a series of compounds with particular activity as inhibitors of the serine-threonine kinase AKT. Also provided are pharmaceutical compositions comprising same as well as methods for treating cancer.

  本发明涉及一系列化合物，其具有特定的抑制丝氨酸/苏氨酸激酶AKT活性的作用。还提供了包含该化合物的制药组合物，以及治疗癌症的方法。