Triethyl 1-(formylamino)-5-(methanesulfonyloxy)-3-methylene-1,1,5-pentane tricarboxylate | 104573-02-6

• 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: Triethyl 1-(formylamino)-5-(methanesulfonyloxy)-3-methylene-1,1,5-pentane tricarboxylate
• 英文别名: Triethyl 1-formamido-3-methylidene-5-methylsulfonyloxypentane-1,1,5-tricarboxylate
• CAS: 104573-02-6
• 化学式: C₁₇H₂₇NO₁₀S
• 分子量: 437.468
• InChiKey: HNMLHCCEMYCFNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  29
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  160
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Triethyl 1-(formylamino)-5-(methanesulfonyloxy)-3-methylene-1,1,5-pentane tricarboxylate 在 Lindlar's catalyst sodium azide 、 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 diethyl 2-(ethoxycarbonyl)-2-formamido-4-methylene-6-<(tert-butoxycarbonyl)amino>-1,7-heptanedioate
  参考文献：
  名称：

  The lysine pathway as a target for a new genera of synthetic antibacterial antibiotics?

  摘要：

  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.

  DOI：

  10.1021/jm00156a021
• 作为产物：
  描述：

  Triethyl 1-(formylamino)-5-hydroxy-3-methylene-1,1,5-pentanetricarboxylate 、 甲基磺酰氯 在 吡啶 作用下， 反应 15.0h， 生成 Triethyl 1-(formylamino)-5-(methanesulfonyloxy)-3-methylene-1,1,5-pentane tricarboxylate
  参考文献：
  名称：

  The lysine pathway as a target for a new genera of synthetic antibacterial antibiotics?

  摘要：

  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.

  DOI：

  10.1021/jm00156a021

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。
• Novel heterocyclic dicarboxylic acids
  申请人：Roussel Uclaf

  公开号：US05081135A1

  公开（公告）日：1992-01-14

  A compound selected from the group consisting of a compound of the formula ##STR1## wherein the dotted lines represent a possible endo or exo double bond, R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, aryl of 6 to 14 carbon atoms, aralkyl of 7 to 18 carbon atoms and ##STR2## R'.sub.2 is alkyl of 1 to 8 carbon atoms or aryl of 6 to 14 carbon atoms, X is --O-- or --NR--, R is selected from the group consisting of hydrogen ##STR3## and --COOR', R' is hydrogen or alkyl of 1 to 8 carbon atoms, Y is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms and alkenyl and alkynyl of 2 to 8 carbon atoms, all optionally substituted with at least one halogen or --OH, with the proviso that if Y is --OH, X is not --NH-- and their non-toxic, pharmaceutically acceptable addition salts of acids or bases having antibacterial and immunological properties.

  该化合物选自以下化合物组：公式## STR1 ##其中虚线代表可能的内部或外部双键，R.sub.1和R.sub.2分别选自以下组：氢，1至8个碳原子的烷基，2至8个碳原子的烯基和炔基，6至14个碳原子的芳基，7至18个碳原子的芳基烷基和## STR2 ## R'.sub.2是1至8个碳原子的烷基或6至14个碳原子的芳基，X是- O-或-NR-，R选自以下组：氢，## STR3 ##和-COOR'，R'是氢或1至8个碳原子的烷基，Y选自以下组：氢，1至8个碳原子的烷基和2至8个碳原子的烯基和炔基，所有这些基团都可以被至少一个卤素或-OH取代，但是如果Y是-OH，则X不是-NH-，并且它们的非毒性，药学上可接受的酸或碱盐具有抗菌和免疫性能。