3-(1H-Indol-3-yl)-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid benzyl ester | 131792-12-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(1H-Indol-3-yl)-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid benzyl ester
• 英文别名: benzyl 3-(1H-indol-3-yl)-2-(triphenyl-lambda5-phosphanylidene)propanoate；benzyl 3-(1H-indol-3-yl)-2-(triphenyl-λ5-phosphanylidene)propanoate
• CAS: 131792-12-6
• 化学式: C₃₆H₃₀NO₂P
• 分子量: 539.613
• InChiKey: CFYWRXVNGJCEPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(1H-Indol-3-yl)-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid benzyl ester 在 sodium periodate 、 N-甲基吲哚酮 、 sodium carbonate 、 二溴三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.67h， 生成 Benzyl (4RS)-(E)-4-Bromo-5-<(tert-butoxycarbonyl)amino>-2-(3-indolylmethyl)-2-pentenoate
  参考文献：
  名称：

  Novel methodology for the synthesis of trans-alkene dipeptide isosteres

  摘要：

  Natural amino acids were converted to the corresponding allylic alcohols A, from which key precursors C were obtained via a three-step sequence [(a) Ac2O/Py or CbzOSu/Et3N/DMAP; (b) NMO/NaIO4/OsO4(cat.); (c) Ph3P = CR2CO2Bn]. The allylic alcohols D were further transformed to the desired pseudodipeptides I through the corresponding bromo derivatives E via a reductive deconjugation process.

  DOI：

  10.1021/jo00006a027

文献信息

• Amide bond surrogates: A general synthetic route to trans carbon-carbon double bono isosteres.
  作者：Youe-Kong Shue、George M. Carrera、Alex M. Nadzan

  DOI：10.1016/s0040-4039(00)95477-7

  日期：1987.1

  A practical synthesis toward trans double bond replacements of amide bond pseudo-peptides has been accomplished. This methodology provides a general route to a wide range of modified peptide analogs which may have biological significance.

  已经完成了对酰胺键伪肽的反式双键置换的实用合成。该方法学提供了获得广泛的修饰的肽类似物的一般途径，这些修饰的肽类似物可能具有生物学意义。
• US5340802A
  申请人：——

  公开号：US5340802A

  公开（公告）日：1994-08-23
• Novel methodology for the synthesis of trans-alkene dipeptide isosteres
  作者：Youe Kong Shue、George M. Carrera、Michael D. Tufano、Alex M. Nadzan

  DOI：10.1021/jo00006a027

  日期：1991.3

  Natural amino acids were converted to the corresponding allylic alcohols A, from which key precursors C were obtained via a three-step sequence [(a) Ac2O/Py or CbzOSu/Et3N/DMAP; (b) NMO/NaIO4/OsO4(cat.); (c) Ph3P = CR2CO2Bn]. The allylic alcohols D were further transformed to the desired pseudodipeptides I through the corresponding bromo derivatives E via a reductive deconjugation process.