l-malic acid dibutyl ester | 2385-79-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: l-malic acid dibutyl ester
• 英文别名: linksdrehender Oxy-bernsteinsaeure-dibutylester；l-Aepfelsaeure-dibutylester；Dibutyl (s)-malate；dibutyl (2S)-2-hydroxybutanedioate
• CAS: 2385-79-7
• 化学式: C₁₂H₂₂O₅
• 分子量: 246.304
• InChiKey: PDSCSYLDRHAHOX-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  l-malic acid dibutyl ester 、 N-叔丁氧羰基-L-丙氨酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以81%的产率得到dibutyl 2(S)-<<(tert-butoxycarbonyl)-(S)-alanyl>oxy>-1,4-butanedioate
  参考文献：
  名称：

  Synthesis of modified partial structures of the bacterial cell wall. 1. Lipopeptides containing nonproteinogenic amino acids

  摘要：

  Two stereoisomeric lipopeptides 1 and 2 which can be regarded as modified peptidoglycans have been synthesized by using three different reaction sequences. The ene reaction of the alpha-allylated dipeptide 12 with butyl glyoxylate was used as a key step. The required enantiomerically pure substrates 9, 10, and 23 were obtained by enzymatic hydrolysis of the corresponding racemic alpha-allylated esters. The absolute configuration of both stereoisomers 1 and 2 was assigned by oxidative cleavage of the double bond in 18 and 19 followed by comparison of the esterified degradation products 28 and 29 with samples of authentic configuration, derived from (R)- and (S)-malic acid.

  DOI：

  10.1021/jo00055a022
• 作为产物：
  描述：

  L-苹果酸 、 正丁醇 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以89%的产率得到l-malic acid dibutyl ester
  参考文献：
  名称：

  Synthesis of modified partial structures of the bacterial cell wall. 1. Lipopeptides containing nonproteinogenic amino acids

  摘要：

  Two stereoisomeric lipopeptides 1 and 2 which can be regarded as modified peptidoglycans have been synthesized by using three different reaction sequences. The ene reaction of the alpha-allylated dipeptide 12 with butyl glyoxylate was used as a key step. The required enantiomerically pure substrates 9, 10, and 23 were obtained by enzymatic hydrolysis of the corresponding racemic alpha-allylated esters. The absolute configuration of both stereoisomers 1 and 2 was assigned by oxidative cleavage of the double bond in 18 and 19 followed by comparison of the esterified degradation products 28 and 29 with samples of authentic configuration, derived from (R)- and (S)-malic acid.

  DOI：

  10.1021/jo00055a022

文献信息

• An expeditive and green chemo-enzymatic route to diester sinapoyl-<scp>l</scp>-malate analogues: sustainable bioinspired and biosourced UV filters and molecular heaters
  作者：Benjamin Rioux、Louis M. M. Mouterde、Jimmy Alarcan、Temitope T. Abiola、Matthias J. A. Vink、Jack M. Woolley、Aurélien A. M. Peru、Matthieu M. Mention、Fanny Brunissen、Giel Berden、Jos Oomens、Albert Braeuning、Vasilios G. Stavros、Florent Allais

  DOI：10.1039/d3sc04836e

  日期：——

  A highly regioselective lipase-catalyzed transesterification enabled the synthesis of sinapoyl malate diesters with fatty chains that proved to be exceptional UV filters and molecular heaters for plants.

  通过脂肪酶催化的高区域选择性酯交换反应，合成了具有脂肪链的正己酰苹果酸二酯，这些脂肪链被证明是优异的紫外线过滤剂和植物分子加热器。
• Synthesis of modified partial structures of the bacterial cell wall. 1. Lipopeptides containing nonproteinogenic amino acids
  作者：Helmut Schneider、Gerhard Sigmund、Bettina Schricker、Klaus Thirring、Heinz Berner

  DOI：10.1021/jo00055a022

  日期：1993.1

  Two stereoisomeric lipopeptides 1 and 2 which can be regarded as modified peptidoglycans have been synthesized by using three different reaction sequences. The ene reaction of the alpha-allylated dipeptide 12 with butyl glyoxylate was used as a key step. The required enantiomerically pure substrates 9, 10, and 23 were obtained by enzymatic hydrolysis of the corresponding racemic alpha-allylated esters. The absolute configuration of both stereoisomers 1 and 2 was assigned by oxidative cleavage of the double bond in 18 and 19 followed by comparison of the esterified degradation products 28 and 29 with samples of authentic configuration, derived from (R)- and (S)-malic acid.