2-methyl-2-(2'-methylprop-2'-enyl)propanedioate | 78331-65-4

• 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: 2-methyl-2-(2'-methylprop-2'-enyl)propanedioate
• 英文别名: diethyl 2-methyl-2-(2-methylallyl)malonate；Methyl-methallyl-malonsaeure-diethylester；Methallyl-methyl-malonsaeure-diethylester；methyl-(2-methyl-allyl)-malonic acid diethyl ester；diethyl methyl-(2-methyl-2-propenyl)-propanedioate；Diethyl 2-methyl-2-(2-methylprop-2-enyl)propanedioate
• CAS: 78331-65-4
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: FDQVHMSKOAZVCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  2-methyl-2-(2'-methylprop-2'-enyl)propanedioate 在 氢氧化钾 、 三氯化铝 作用下， 反应 5.0h， 生成 2,4-dimethyl-4-phenylpentanoic acid
  参考文献：
  名称：

  Fallon, Gary D.; Holland, Kelvyn A.; Rae, Ian D., Australian Journal of Chemistry, 1990, vol. 43, # 3, p. 521 - 533

  摘要：

  DOI：
• 作为产物：
  描述：

  5-(methallyl)-1,2,3,4,5-penta(4-acetylphenyl)cyclopentadiene 、 甲基丙二酸二乙酯 在 sodium hydride 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 4.25h， 以71%的产率得到2-methyl-2-(2'-methylprop-2'-enyl)propanedioate
  参考文献：
  名称：

  取代的环戊二烯基阴离子向氧化加成的离去基电位

  摘要：

  证明了取代的环戊二烯基阴离子可以用作钯催化的烯丙基化反应的离去基团的设施。显示了几种烯丙基环戊二烯基底物的反应。碳与氮的亲核取代是通过烯丙基五-对乙酰基苯基环戊二烯与N-甲基苄基胺的脱甲酰作用实现的。

  DOI：

  10.1021/ol901598n

文献信息

• TETRAHYDROFURANS: I. 2,2-DIMETHYL-4-SUBSTITUTED-4-HYDROXYMETHYLTETRAHYDROFURANS AND RELATED COMPOUNDS
  作者：B. K. Wasson、C. H. Gleason、I. Levi、J. M. Parker、L. M. Thompson、C. H. Yates

  DOI：10.1139/v61-113

  日期：1961.4.1

  xymethyltetrahydrofuran (IVe) with acetic anhydride – pyridine hydrochloride yielded 2-allyl-2-methallyl-1,3-propanediol diacetate (Xe). Catalytic reduction of IVe gave 2,2-dimethyl-4-n-propyl-4-hydroxymethyltetrahydrofuran (IVd). Reductive cleavage of the tosylate VIIIb of 2,2,4-trimethyl-4-hydroxymethyltetrahydrofuran (IVb) with lithium aluminum hydride yielded the known 2,2,4,4-tetramethyltetrahydrofuran

  取代的甲基烯丙基丙二酸酯 (I) 用氢化铝锂还原成相应的 2-甲基烯丙基-1,3-丙二醇 (II)。这些二醇II在用无机酸处理后环化成异构的2,2-二甲基-4-取代-4-羟甲基四氢呋喃(IV)。II 和 IV 分别转化为氨基甲酸酯 III 和 V，显示出药理活性。通过红外分析和以下转化证明了环状化合物IV的指定结构。2,2-二甲基-4-烯丙基-4-羟甲基四氢呋喃 (IVe) 与乙酸酐 - 吡啶盐酸盐的断环产生 2-烯丙基-2-甲基烯丙基-1,3-丙二醇二乙酸酯 (Xe)。IVe 的催化还原得到 2,2-二甲基-4-n-丙基-4-羟甲基四氢呋喃 (IVd)。2,2 的甲苯磺酸盐 VIIIb 的还原裂解，
• Reactions of organocobalt complexes with bromoesters: regiospecific synthesis of allyl- and cyclopropylmethyl-substituted malonic and acetoacetic esters
  作者：M. Veber、K.N-.V- Duong、A. Gaudemer、M.D. Johnson

  DOI：10.1016/s0022-328x(00)81195-x

  日期：1981.4

  Allyl(pyridine)cobaloximes RCo(dmgH)2Py (R = allyl) react readily with diethyldibromomalonate, diethylbromomethylmalonate and ethyl 2-bromoacetoacetate to give the corresponding allyl-substituted esters. Transfer of the allyl group occurs with complete rearrangement in all but one cases. Buten-3-yl(pyridine)cobaloximes react with diethylbromomalonate giving cyclopropylmethylmalonic esters.

  烯丙基（吡啶）钴肟肟RCo（dmgH）2 Py（R =烯丙基）与二乙基二溴丙二酸酯，二乙基溴甲基丙二酸酯和2-溴乙酰乙酸乙酯容易反应，得到相应的烯丙基取代的酯。除一种情况外，烯丙基的转移均发生完全重排。丁-3-基（吡啶）钴肟与溴代丙二酸二乙酯反应，生成环丙基甲基丙二酸酯。
• Novel aminopimelic acids
  申请人：Roussel Uclaf

  公开号：US05030715A1

  公开（公告）日：1991-07-09

  A) Compounds selected from the group consisting of a compound of the formula ##STR1## wherein U is ##STR2## m and n are individually 1 or 2 of one, the dotted lines is a single double bond optionally of cis or trans configuration, a is selected from the group consisting of hydrogen, methyl and methylene, Y is selected from the group consisting of hydrogen, residue of an amino acid with an .alpha.-or .omega.-carboxyl and a peptide or 2,3 or 4 amino acids with the amine optionally acylated with an optionally unsaturated aliphatic carboxylic acid of 6 to 24 carbon atoms or alkylated with alkyl of 1 to 8 carbon atoms, R is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon, alkenyl and alkynyl of 2 to 8 carbon atoms optionally substituted with at least one halogen with the proviso that if Y is hydrogen, alanine or proline and if a is hydrogen, U contains a double bond; and B) their non-toxic, pharmaceutically acceptable salts with bases or acids, the alkyl esters of 1 to 6 carbon atoms and their primary and secondary amides having remarkable immunomodulatric properties and anti-bacterial activity.

  从以下化合物组合中选择化合物：其中U为##STR2##，m和n分别为1或2，虚线是一根单独的双键，可选为顺式或反式构型，a选择自氢、甲基和亚甲基组成的群，Y选择自氢、一种氨基酸的残基，具有α-或ω-羧基和一个肽或2、3或4个氨基酸，其胺基可选择酰化，酰基为6至24个碳原子的不饱和脂肪族羧酸或烷基化，烷基为1至8个碳原子，R选择自氢、1至8个碳原子的烷基、2至8个碳原子的烯烃和炔烃，可选择地取代至少一种卤素，但若Y为氢、丙氨酸或脯氨酸，且a为氢，则U含有双键；以及它们与碱或酸形成的非毒性、药用接受的盐、1至6个碳原子的烷基酯及具有显著的免疫调节性质和抗菌活性的一级和二级酰胺。
• de Moura Campos,M.; do Amaral,L., Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft, 1965, vol. 298, # 2, p. 92 - 100
  作者：de Moura Campos,M.、do Amaral,L.

  DOI：——

  日期：——
• Nickel-Catalyzed Arylative Ring-Opening of 3-Methylenecycloalkane-1,1-dicarboxylates
  作者：Yuto Sumida、Hideki Yorimitsu、Koichiro Oshima

  DOI：10.1021/ol100599c

  日期：2010.5.21

  An arylative ring-opening reaction of cyclic allylmalonates with arylzinc reagents under nickel catalysis has been developed. Upon the ring-opening sp(3)C-sp(3)C bond cleavage, the allylic moiety serves as an allylic electrophile to react with arylzinc reagents. Simultaneously, the malonate moiety is converted to the corresponding zinc enolate, which can react further with electrophiles. The overall process increases molecular complexity and diversity starting from readily available substrates and is useful in organic synthesis.