dimethyl (S)-2-(benzylidenamino)pentanedioate

• 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: dimethyl (S)-2-(benzylidenamino)pentanedioate
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: AFQVWKBRDSOMCX-XBUHWIKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  64.96
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  dimethyl (S)-2-(benzylidenamino)pentanedioate 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.17h， 生成 dimethyl (-)-(S)-2-[N-benzyl-N-(2-chloroacetyl)amino]pentanedioate
  参考文献：
  名称：

  Synthesis of chiral non-racemic 3-(dioxopiperazin-2-yl)propionic acid derivatives

  摘要：

  Starting with the proteinogenic amino acid (S)-glutamate (3) a facile, high yielding synthesis of the chiral non-racemic 3-(dioxo-piperazin-2-yl)propionates 6, 11, and 14 is presented. Key intermediates in the synthesis of Ne-benzyl substituted (dioxopiperazin-2-yl)propionates 11 and 14 are the N-monobenzylglutamate 8 and the chloroacetamide 12, which allow introduction of various substituents in position 4 of the piperazine ring. In receptor binding studies with radioligands the 3-(piperazin-2-yl)propanol 15 was found to have promising affinity for sigma(1)-receptors (K-i=66.1 nM). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01212-1
• 作为产物：
  描述：

  L-谷氨酸 在 sodium sulfate 、 三乙胺 作用下， 以 甲醇 、 正戊烷 为溶剂， 反应 32.0h， 生成 dimethyl (S)-2-(benzylidenamino)pentanedioate
  参考文献：
  名称：

  Synthesis of chiral non-racemic 3-(dioxopiperazin-2-yl)propionic acid derivatives

  摘要：

  Starting with the proteinogenic amino acid (S)-glutamate (3) a facile, high yielding synthesis of the chiral non-racemic 3-(dioxo-piperazin-2-yl)propionates 6, 11, and 14 is presented. Key intermediates in the synthesis of Ne-benzyl substituted (dioxopiperazin-2-yl)propionates 11 and 14 are the N-monobenzylglutamate 8 and the chloroacetamide 12, which allow introduction of various substituents in position 4 of the piperazine ring. In receptor binding studies with radioligands the 3-(piperazin-2-yl)propanol 15 was found to have promising affinity for sigma(1)-receptors (K-i=66.1 nM). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01212-1

文献信息

• Sodium borohydride: A versatile reagent in the reductive <i>N</i>-monoalkylation of α-amino acids and α-amino methyl esters
  作者：Giancarlo Verardo、Paola Geatti、Elena Pol、Angelo G Giumanini

  DOI：10.1139/v02-083

  日期：2002.7.1

  α-Amino acids and α-amino methyl esters are easily converted to their N-monoalkyl derivatives by a reductive condensation reaction using several carbonyl compounds in the presence of sodium borohydride. This reducing agent has shown a wide versatility with minor but essential procedural variations. The reaction allows the α-monodeuterium labeling of the new N-substituent by use of sodium borodeuteride.Key words: α-amino acid, α-amino methyl esters, sodium borohydride, reductive N-monoalkylation, carbonyl compounds.

  α-氨基酸和α-氨基甲酯可以通过还原缩合反应在存在苏打硼氢化钠的情况下，利用几种羰基化合物轻松转化为它们的N-单烷基衍生物。这种还原剂在轻微但必要的程序变化下显示出广泛的多功能性。该反应允许通过使用苏打硼氘化钠对新的N-取代基进行α-单氘标记。关键词：α-氨基酸，α-氨基甲酯，苏打硼氢化钠，还原性N-单烷基化，羰基化合物。
• Electroreductive Intramolecular Coupling of Aromatic Imino Esters:  Is Four-Membered Cyclization Much More Favorable than Six-Membered Cyclization?
  作者：Naoki Kise、Yuuki Hirano、Yoshi Tanaka

  DOI：10.1021/ol053144x

  日期：2006.3.1

  electroreduction of an aromatic imino ester prepared from (S)-glutamic acid in the presence of chlorotrimethylsilane and triethylamine afforded a four-membered cyclized product, a mixed ketal of cis-2,4-disubstituted azetidine-3-one, stereospecifically. Calculations for the transition states by the DFT method support the predominant formation of the azetidine. The electroreduction of an aromatic imino ester prepared

  [反应：见正文]在氯代三甲基硅烷和三乙胺的存在下，由（S）-谷氨酸制得的芳族亚氨基酯的电还原得到四元环化产物，即顺式-2,4-二取代氮杂环丁烷-3的混合缩酮-一，立体定向。通过DFT方法对过渡态的计算支持了氮杂环丁烷的主要形成。由（S）-天冬氨酸制得的芳香亚氨基酯的电还原得到几乎等量的顺式-2,4-二取代的氮杂环丁烷-3-酮非对映体纯的混合缩酮和2,5-二取代的吡咯烷-的非对映体混合物3个
• Synthesis of chiral non-racemic 3-(dioxopiperazin-2-yl)propionic acid derivatives
  作者：Manuela Weigl、Bernhard Wünsch

  DOI：10.1016/s0040-4020(01)01212-1

  日期：2002.2

  Starting with the proteinogenic amino acid (S)-glutamate (3) a facile, high yielding synthesis of the chiral non-racemic 3-(dioxo-piperazin-2-yl)propionates 6, 11, and 14 is presented. Key intermediates in the synthesis of Ne-benzyl substituted (dioxopiperazin-2-yl)propionates 11 and 14 are the N-monobenzylglutamate 8 and the chloroacetamide 12, which allow introduction of various substituents in position 4 of the piperazine ring. In receptor binding studies with radioligands the 3-(piperazin-2-yl)propanol 15 was found to have promising affinity for sigma(1)-receptors (K-i=66.1 nM). (C) 2002 Elsevier Science Ltd. All rights reserved.