(9H-fluoren-9-yl)methyl N-[(2-{1,1-dimethyl-2-[methyl(phenyl)amino]-2-thioxoethyl}amino)-2-oxoethyl]carbamate | 457058-36-5

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: (9H-fluoren-9-yl)methyl N-[(2-{1,1-dimethyl-2-[methyl(phenyl)amino]-2-thioxoethyl}amino)-2-oxoethyl]carbamate
• 英文别名: Fmoc-Gly-Aib-Ψ(CS)-N(Me)Ph
• CAS: 457058-36-5
• 化学式: C₂₈H₂₉N₃O₃S
• 分子量: 487.623
• InChiKey: PCNAJKGCTLDBSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  70.67
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (9H-fluoren-9-yl)methyl N-[(2-{1,1-dimethyl-2-[methyl(phenyl)amino]-2-thioxoethyl}amino)-2-oxoethyl]carbamate 在 lithium hydroxide 、 camphor-10-sulfonic acid 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 溶剂黄146 、 二乙胺 、 N,N-二异丙基乙胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 279.53h， 生成 Boc-Trp-Ile-Gly-[1,3-thiazol-5(4H)-imine]Aib-Ile-Val-Aib-Leu-Aib-Pro-Ome
  参考文献：
  名称：

  Formation of 1,3-Thiazol-5(4H)-imines and 1,3-Oxazol-5(4H)-imines in Aib-Containing Thiopeptides

  摘要：

  When tripeptides of type Axx'-Aib-Axx-OH were coupled with amino acid methyl esters by means of commonly used coupling reagents, the formation of 1,3-thiazol-5(4H)-imines and 1,3-oxazol-5(411)-imines was observed. With the aim Of understanding which structure elements are required for this reaction, several model peptides have been prepared according to our recently described methodology, a modification of the 'azirine/oxazolone method', followed by selective isomerization of the peptide thioamides. In addition, attempts to prepare peptides that contain more than one C=S group by the same methodology also led to the formation of 1,3-thiazol-5(4H)-imine-containing derivatives. An additional C=S group can be introduced into the peptide, when the 1,3-thiazol-5(4H)-imines were treated with H2S, although mixtures of epimers were obtained. The structures of an endothiohexapeptide, two 1,3-thiazol-5(4H)-imine, and two peptides containing a 1,3-thiazol5(4H)-imine moiety have been established by X-ray crystal-structure analysis.

  DOI：

  10.1002/1522-2675(200204)85:4<990::aid-hlca990>3.0.co;2-6
• 作为产物：
  描述：

  2,2-dimethyl-3-(N-methyl-N-phenylamino)-2H-azirine 在 N-甲基吗啉 、 盐酸 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 46.08h， 生成 (9H-fluoren-9-yl)methyl N-[(2-{1,1-dimethyl-2-[methyl(phenyl)amino]-2-thioxoethyl}amino)-2-oxoethyl]carbamate
  参考文献：
  名称：

  Formation of 1,3-Thiazol-5(4H)-imines and 1,3-Oxazol-5(4H)-imines in Aib-Containing Thiopeptides

  摘要：

  When tripeptides of type Axx'-Aib-Axx-OH were coupled with amino acid methyl esters by means of commonly used coupling reagents, the formation of 1,3-thiazol-5(4H)-imines and 1,3-oxazol-5(411)-imines was observed. With the aim Of understanding which structure elements are required for this reaction, several model peptides have been prepared according to our recently described methodology, a modification of the 'azirine/oxazolone method', followed by selective isomerization of the peptide thioamides. In addition, attempts to prepare peptides that contain more than one C=S group by the same methodology also led to the formation of 1,3-thiazol-5(4H)-imine-containing derivatives. An additional C=S group can be introduced into the peptide, when the 1,3-thiazol-5(4H)-imines were treated with H2S, although mixtures of epimers were obtained. The structures of an endothiohexapeptide, two 1,3-thiazol-5(4H)-imine, and two peptides containing a 1,3-thiazol5(4H)-imine moiety have been established by X-ray crystal-structure analysis.

  DOI：

  10.1002/1522-2675(200204)85:4<990::aid-hlca990>3.0.co;2-6