diethyl-2-(2-bromoethylidene)malonte | 51385-79-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: diethyl-2-(2-bromoethylidene)malonte
• 英文别名: diethyl-2-bromoethylidene malonate；Diethyl (2-bromoethylidene)propanedioate；diethyl 2-(2-bromoethylidene)propanedioate
• CAS: 51385-79-6
• 化学式: C₉H₁₃BrO₄
• 分子量: 265.104
• InChiKey: XSLZBBONCONAIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl-2-(2-bromoethylidene)malonte 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 diethyl 2-<2-(2-aminopurin-9-yl)ethyl>malonate
  参考文献：
  名称：

  Regiospecific Michael additions with 2-aminopurines

  摘要：

  N-9 alkylated materials are the sole products obtained from extended reaction of 2-aminopurines (potential guanine precursors) with Michael acceptors. This was used as the basis for a highly regioselective synthesis of famciclovir. the oral form of the anti-herpesvirus agent penciclovir.

  DOI：

  10.1016/s0040-4039(00)61326-6
• 作为产物：
  描述：

  dimethyloxosulfonium-3,3-dicarboethoxyallylide 在 氢溴酸 作用下， 以 二氯甲烷 、 水 为溶剂， 以55%的产率得到diethyl-2-(2-bromoethylidene)malonte
  参考文献：
  名称：

  通过一个碳原子的延伸方便合成2-（2-卤代亚乙基）丙二酸二烷基酯，氰基乙酸酯和卤代巴豆酸酯

  摘要：

  2-卤代亚乙基丙二酸酯是高反应性物种，是用于合成抗病毒药物Famvir®的有用合成子。没有制备2-卤代亚烷基丙二酸酯的简单方法。我们已经开发了一种新颖且不麻烦的方法，该方法通过二甲基（2-烷氧基亚甲基）丙二酸酯，氰基乙酸酯和3-烷氧基丙烯酸酯与一个二甲基亚砜基的碳原子延伸来合成2-（2-卤代亚乙基）丙二酸二烷基酯，氰基乙酸酯和卤代巴豆酸酯。

  DOI：

  10.1016/j.tetlet.2015.05.015

文献信息

• Acyclic and Cyclopropyl Analogues of Adenosine Bisphosphate Antagonists of the P2Y₁ Receptor:  Structure−Activity Relationships and Receptor Docking
  作者：Hak Sung Kim、Dov Barak、T. Kendall Harden、José L. Boyer、Kenneth A. Jacobson

  DOI：10.1021/jm010082h

  日期：2001.9.1

  to platelet aggregation, and selective antagonists are sought as potential antithrombotic agents. We reported (Kim et al. J. Med. Chem. 2000, 43, 746-755) that acyclic analogues of adenine nucleotides, containing two phosphate groups on a symmetrically branched aliphatic chain, attached at the 9-position of adenine, are moderately potent P2Y1 receptor antagonists. In this study we have varied the chain

  血小板中 P2Y1 受体的激活有助于血小板聚集，因此寻求选择性拮抗剂作为潜在的抗血栓剂。我们报道 (Kim et al. J. Med. Chem. 2000, 43, 746-755) 腺嘌呤核苷酸的无环类似物，在对称支链脂肪链上含有两个磷酸基团，连接在腺嘌呤的 9 位强效 P2Y1 受体拮抗剂。在这项研究中，我们改变了链结构，包括不对称取代、烯属和环丙基。这些拮抗剂在微摩尔范围内抑制由 30 nM 2-MeS-ADP 诱导的火鸡红细胞膜中的磷脂酶 C 的刺激。在被两个磷酸基团取代的一系列对称支化脂肪族基团中，最佳拮抗剂效力发生在 2-甲基丙基基团。2-氯-N(6)-甲基腺嘌呤衍生物，2-[2-(2-chloro-6-methylaminopurin-9-yl)methyl]propane-1,3-bisoxy(diammoniumphosphate) (7)，是一个完整的P2Y1 受体拮抗剂，IC(50)
• Process for the preparation of purine derivatives as antiviral agents
  申请人：Beecham Group p.l.c.

  公开号：US05220024A1

  公开（公告）日：1993-06-15

  A process for the preparation of a compound of formula (A): ##STR1## wherein X is hydrogen, hydroxy, chloro, C.sub.1-6 alkoxy or phenyl C.sub.1-6 alkoxy and R.sub.a and R.sub.b are hydrogen, including acyl and phosphate derivatives thereof; which process comprises: i) the preparation of a compound of formula (I): ##STR2## wherein R.sub.1 is C.sub.1-6 alkyl, or phenyl C.sub.1-6 alkyl in which the phenyl group is optionally substituted; R.sub.2 is hydrogen, hydroxy, chlorine, C.sub.1-6 alkoxy, phenyl C.sub.1-6 alkoxy or amino; and R.sub.3 is halogen, C.sub.1-6 alkylthio, C.sub.1-6 alkylsulphonyl, azido, an amino group or a protected amino group, which process comprises the reaction of a compound of formula (II): ##STR3## with a compound of formula (VII): ##STR4## wherein Q is a leaving group, J is hydrogen or halo and R.sub.1 is as hereinbefore defined; to give a compound of formula (VIII): ##STR5## followed by reduction of the compound of formula (VIII) to give a compound of formula (I) as hereinbefore defined; and, as necessary or desired, interconverting variables R.sub.1, R.sub.2 and R.sub.3 to further values of R.sub.1, R.sub.2 and R.sub.3 ; (ii) the conversion of the resulting compound of formula (I) to a compound of formula (A) by converting variable R.sub.3, when other than amino, to amino, reducing the ester groups CO.sub.2 R.sub.1 to CH.sub.2 OH and optionally forming acyl or phosphate derivatives thereof, and as necessary or desired converting variable R.sub.2 in the compound of formula (I) to variable X in the compound of formula (A).

  一种制备式（A）化合物的方法：其中X为氢、羟基、氯、C.sub.1-6烷氧基或苯基C.sub.1-6烷氧基，R.sub.a和R.sub.b为氢，包括酰基和磷酸酯衍生物；该方法包括：i）制备式（I）化合物：其中R.sub.1为C.sub.1-6烷基或苯基C.sub.1-6烷基，其中苯基可以选择性取代；R.sub.2为氢、羟基、氯、C.sub.1-6烷氧基、苯基C.sub.1-6烷氧基或氨基；R.sub.3为卤素、C.sub.1-6烷基硫醇、C.sub.1-6烷基磺酰、叠氮化物、氨基或保护氨基，其中该过程包括化合物式（II）与化合物式（VII）的反应：其中Q为离去基团，J为氢或卤素，R.sub.1如上所述，得到化合物式（VIII），然后还原化合物式（VIII）得到化合物式（I），如有必要或需要，可以将变量R.sub.1、R.sub.2和R.sub.3互相转化为R.sub.1、R.sub.2和R.sub.3的其他值；ii）将所得到的化合物式（I）转化为化合物式（A），通过将变量R.sub.3（当不是氨基时）转化为氨基，将酯基CO.sub.2R.sub.1还原为CH.sub.2OH，并选择性地形成酰基或磷酸酯衍生物，如有必要或需要，将化合物式（I）中的变量R.sub.2转化为化合物式（A）中的变量X。
• Regioselective N-Alkylation of 4-Formylimidazole
  作者：Qiaogong Su、Jeffery L. Wood

  DOI：10.1080/00397910008086978

  日期：2000.9

  We describe here a high yield and highly regioselective N-alkylation of 4-formylimidazole via reversible Michael Reaction.
• A convenient synthesis of dialkyl 2-(2-haloethylidene)malonates, cyanoacetates and halocrotonates by one carbon extension
  作者：S. Sathishkumar、S. Mahasampathgowri、K.K. Balasubramanian、R. Saiganesh

  DOI：10.1016/j.tetlet.2015.05.015

  日期：2015.6

  and useful synthons for the synthesis of Famvir®, an antiviral drug. Simple methods for the preparation of 2-haloalkylidenemalonates are not available. We have developed a novel and non-cumbersome methodology for the synthesis of dialkyl 2-(2-haloethylidene)malonates, cyanoacetates and halocrotonates by one carbon extension of dialkyl (2-alkoxymethylene)malonates, cyanoacetates and 3-alkoxyacrylates with

  2-卤代亚乙基丙二酸酯是高反应性物种，是用于合成抗病毒药物Famvir®的有用合成子。没有制备2-卤代亚烷基丙二酸酯的简单方法。我们已经开发了一种新颖且不麻烦的方法，该方法通过二甲基（2-烷氧基亚甲基）丙二酸酯，氰基乙酸酯和3-烷氧基丙烯酸酯与一个二甲基亚砜基的碳原子延伸来合成2-（2-卤代亚乙基）丙二酸二烷基酯，氰基乙酸酯和卤代巴豆酸酯。
• Regiospecific Michael additions with 2-aminopurines
  作者：Graham R. Geen、Peter M. Kincey、Bernadette M. Choudary

  DOI：10.1016/s0040-4039(00)61326-6

  日期：1992.8

  N-9 alkylated materials are the sole products obtained from extended reaction of 2-aminopurines (potential guanine precursors) with Michael acceptors. This was used as the basis for a highly regioselective synthesis of famciclovir. the oral form of the anti-herpesvirus agent penciclovir.