pentachlorophenyl 5-oxo-(S)-2-tetrahydrofurancarboxylate | 192050-80-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: pentachlorophenyl 5-oxo-(S)-2-tetrahydrofurancarboxylate
• 英文别名: Pentachlorophenyl (2s)-5-oxo-2-tetrahydrofurancarboxylate；(2,3,4,5,6-pentachlorophenyl) (2S)-5-oxooxolane-2-carboxylate
• CAS: 192050-80-9
• 化学式: C₁₁H₅Cl₅O₄
• 分子量: 378.423
• InChiKey: IXKIYKAGFGNCBS-VKHMYHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  pentachlorophenyl 5-oxo-(S)-2-tetrahydrofurancarboxylate 在 palladium on activated charcoal 吡啶 、 sodium azide 、 乙醇 、 氯仿 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 25.0~60.0 ℃ 、310.27 kPa 条件下， 反应 45.0h， 生成 (2S)-2-hydroxy-1-N-(hydrochloride 6-amino-n-hexyl)amidopentan-5-oic acid 5,2-lactone
  参考文献：
  名称：

  Stereocontrolled synthesis of stereoregular, chiral analogs of nylon 5, 5 and nylon 5,6

  摘要：

  L-glutamic acid (1) was employed as a chiral template in the preparation of the pentachlorophenyl ester of (4S)-carboxy-1,4-butirolactone (3), a key precursor of chiral analogs of nylon 5,5 and nylon 5,6. Stereocontrol in the synthesis of these polymers was achieved by chemoselective condensation of the ester group of 3 with aminoalcohols. The alcohol function of the resulting N-(hydroxyalkyl)amides (4 and 9) was converted into amine by tosylation, azide substitution and hydrogenolysis. The amino lactones 7 and 12 thus obtained were conveniently functionalized for the polycondensation, which led to the stereoregular, crystalline polyamides 8 and 13. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00121-3
• 作为产物：
  描述：

  五氯酚 、 (S)-(+)-5-氧代-2-四氢呋喃羧酸 在 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以90%的产率得到pentachlorophenyl 5-oxo-(S)-2-tetrahydrofurancarboxylate
  参考文献：
  名称：

  Stereocontrolled synthesis of stereoregular, chiral analogs of nylon 5, 5 and nylon 5,6

  摘要：

  L-glutamic acid (1) was employed as a chiral template in the preparation of the pentachlorophenyl ester of (4S)-carboxy-1,4-butirolactone (3), a key precursor of chiral analogs of nylon 5,5 and nylon 5,6. Stereocontrol in the synthesis of these polymers was achieved by chemoselective condensation of the ester group of 3 with aminoalcohols. The alcohol function of the resulting N-(hydroxyalkyl)amides (4 and 9) was converted into amine by tosylation, azide substitution and hydrogenolysis. The amino lactones 7 and 12 thus obtained were conveniently functionalized for the polycondensation, which led to the stereoregular, crystalline polyamides 8 and 13. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00121-3

文献信息

• Synthesis of regioisomeric, stereoregular AABB-type polyamides from chiral diamines and diacids derived from natural amino acids
  作者：Romina V. Gómez、Oscar Varela

  DOI：10.1016/j.tetasy.2007.09.010

  日期：2007.9

  which the building blocks derived from 1 and 4 are linked through an amido group. Compounds 11 and 15 are, in fact, α,ω-amino acids having amino and lactone groups, and hence activated for polycondensation. Thus, polymerization of 11 took place under regio- and stereo-control to afford stereoregular poly[N-(1′-amino-(S)-2′-propyl)-carboxyamido-(S)-2-hydroxypentan-5-oic acid] (16). Similar polycondensation

  已经使用1-谷氨酸1和1-丙氨醇4作为手性来源合成了两种区域异构和立构规整的AABB型聚酰胺。从4制备了手性二胺的两种衍生物，并与衍生自1的五氯苯基5-氧代-（S）-2-四氢呋喃羧酸盐3进行区域选择性缩合。官能团的操纵和方便的脱保护导致了N- [1'-氨基-（S）-2'-丙基]-和N -[（S）-2'-氨基-1'-丙基]-的铵盐5-氧代-（S）-2-四氢呋喃羧酰胺11和15分别由1和4衍生的结构单元通过酰胺基连接。实际上，化合物11和15是具有氨基和内酯基的α，ω-氨基酸，因此被活化用于缩聚。因此，在区域和立体控制下进行11的聚合，得到立体规则的聚[ N-（1'-氨基-（S）-2'-丙基）-羧基酰胺基-（S）-2-羟基戊烷-5-oic酸]（16）。在合成16所用的最佳条件下，类似的15的缩聚反应得到了区域异构聚酰胺17，表现出低于16的分子量。描述了光学活性AABB-聚酰胺16和17的热和光谱性质。