ethyl 2-acetamido-2-ethoxycarbonyl-4-methyl-4-pentenoic acid | 37944-29-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-acetamido-2-ethoxycarbonyl-4-methyl-4-pentenoic acid
• 英文别名: diethyl 2-acetamido-2-methallylmalonate；acetylamino-methallyl-malonic acid diethyl ester；Acetylamino-methallyl-malonsaeure-diaethylester；1-Acetamino-3-methyl-buten-(3)-dicarbonsaeure-(1.1)-diaethylester；Acetamino-methallyl-malonsaeure-diaethylester；(acetylamino)(2-methyl-2-propenyl)-propanedioic acid, diethyl ester；Diethyl acetamido(2-methylprop-2-en-1-yl)propanedioate；diethyl 2-acetamido-2-(2-methylprop-2-enyl)propanedioate
• CAS: 37944-29-9
• 化学式: C₁₃H₂₁NO₅
• mdl: MFCD10039347
• 分子量: 271.313
• InChiKey: BXUSHPORVLKTKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-acetamido-2-ethoxycarbonyl-4-methyl-4-pentenoic acid 在 乙醇 、 镍 作用下， 生成 acetylamino-isobutyl-malonic acid diethyl ester
  参考文献：
  名称：

  The Use of Ethyl Acetamidomalonate in the Synthesis of Amino Acids. The Preparation of dl-Histidine, dl-Phenylalanine and dl-Leucine

  摘要：

  DOI：

  10.1021/ja01218a046
• 作为产物：
  描述：

  3-溴-2-甲基丙烯 、 乙酰氨基丙二酸二乙酯 在 sodium ethanolate 作用下， 生成 ethyl 2-acetamido-2-ethoxycarbonyl-4-methyl-4-pentenoic acid
  参考文献：
  名称：

  The Structures of Thiolutin and Aureothricin, Antibiotics Containing a Unique Pyrrolinonodithiole Nucleus

  摘要：

  DOI：

  10.1021/ja01615a058

文献信息

• Syntheses of protected vinylic amino acids by intermolecular Lewis acid catalyzed ene reactions
  作者：K. Agouridas、J.M. Girodeau、R. Pineau

  DOI：10.1016/s0040-4039(00)98632-5

  日期：1985.1

  Intermolecular ene reaction between ethylglyoxylate and allylic amino acid derivatives gave highly functionalized unsaturated pimelic acids in one step. This synthetic approach appears as a new efficient method for the synthesis of vinylic amino acids.

  乙醛酸乙酯与烯丙基氨基酸衍生物之间的分子间烯反应一步就得到了高度官能化的不饱和庚二酸。这种合成方法似乎是合成乙烯基氨基酸的一种新的有效方法。
• The Total Synthesis of Eponemycin
  作者：Ulrich Schmidt、Johannes Schmidt

  DOI：10.1055/s-1994-25464

  日期：——

  Eponemycin, an antibiotic with a highly potent and specific antitumor activity against B16 melanoma cells in vivo, has been synthesized. The framework of the western half of the molecule was built up from N-trityl-γ, δ-didehydroleucinal and the dilithium derivative LiO-CH2C(Li)=CH2. In the final step, a vinyl ketone was oxidized nonstereoselectively to give a mixture of three isomers from which eponemycin was isolated in 40% yield.

  表鬼臼霉素是一种抗生素，具有高度强效且特异性的体内抗B16黑色素瘤细胞活性，现已合成成功。该分子的西半部分结构由N-三苯甲基-γ, δ-二脱氢亮氨醛和二锂衍生物LiO-CH₂C(Li)=CH₂构建而成。在最后一步中，乙烯基酮非立体选择性地氧化生成三种异构体混合物，从中分离得到表鬼臼霉素，产率为40%。
• Peptides Containing γ,δ-Dihydroxy-<scp>l</scp>-leucine
  作者：Benson J. Edagwa、Carol M. Taylor

  DOI：10.1021/jo900459f

  日期：2009.6.5

  (+/-)-Dehydroleucine was prepared and resolved by porcine kidney acylase. Under the conditions of the Sharpless asymmetric dihydroxylation (SAD), employing AD-mix-alpha N alpha-carbobenzyloxy-(2S)-4,5-dehydroleucine methyl ester (16) gave rise to a 6.5:1.0 mixture of gamma-lactones 17, favoring the 4R configuration. Such carbamate-protected alpha-amino-gamma-hydroxylactones are not recommended as intermediates for peptide synthesis, since model studies showed that lactone 13 was unreactive toward an-Lines. Moreover, the lactone ring could not be opened hydrolytically without epimerization at C alpha. N alpha-Carbobenzyioxy-(2S)-4,5-dehydroleucine (22) was condensed with valine ethyl ester (19) to give dipeptide 23. Treatment of 23 with AD-ntix-beta, under the SAD conditions, converted the dehydroleucine residue to gamma,delta-dihydroxyleucine with 4S configuration, as occurs in alloviroidin (3), a natural product isolated from Amanita suballiacea.

  (±)-脱氢亮氨酸的制备及拆分通过猪肾酰酶完成。在夏普莱斯不对称二羟基化（SAD）条件下，使用AD-mix-alpha，α-羧苄氧基-(2S)-4,5-脱氢亮氨酸甲酯（16）生成了6.5:1.0比例的γ-内酯（17），主要为4R构型。这种羰基保护的α-氨基-γ-羟基内酯不建议作为肽合成的中间体，因为模型研究表明，内酯13对α-氨基酸无反应性。此外，内酯环在α位不发生环状水解。α-羧苄氧基-(2S)-4,5-脱氢亮氨酸（22）与缬氨酸乙酯（19）缩合生成二肽（23）。将23与AD-mix-beta在SAD条件下处理，将脱氢亮氨酸残基转化为具有4S构型的γ,δ-二羟基亮氨酸，如alloviroidin（3）（源自Amanita suballiacea的天然产物）。
• Preparation of leucine
  申请人：WINTHROP STEARNS INC

  公开号：US02445817A1

  公开（公告）日：1948-07-27
• The lysine pathway as a target for a new genera of synthetic antibacterial antibiotics?
  作者：Jean Marc Girodeau、Constantin Agouridas、Maryse Masson、Roland Pineau、Francois Le Goffic

  DOI：10.1021/jm00156a021

  日期：1986.6

  Unsaturated analogues of diaminopimelic acid have been synthesized. The amino acids were designed so that they would be reversible or irreversible inhibitors of both of the two last enzymes of the lysine pathway. The compounds were tested with meso-diaminopimelate decarboxylase. trans-3,4-Didehydrodiaminopimelic acid (2) was found to be the most potent inhibitor. The antibacterial activities did not correlate with enzyme inhibiting activities. 4-Methylenediaminopimelic acid 4 showed strong antibacterial properties. It is suggested that L,L-diaminopimelate epimerase could be the target enzyme.