Cbz-Ala-OCH2CCH | 125376-32-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Cbz-Ala-OCH2CCH
• 英文别名: N-[(Phenylmethoxy)carbonyl]-L-alanine 2-propyn-1-yl ester；prop-2-ynyl (2S)-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 125376-32-1
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: WFZWQFXKCGKLTR-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(azidomethyl)-7-hydroxy-2H-chromen-2-one 、 Cbz-Ala-OCH2CCH 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 乙醇 、 水 为溶剂， 以92%的产率得到(1-((7-hydroxy-2-oxo-2H-chromen-4-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl((benzyloxy)carbonyl)-L-alaninate
  参考文献：
  名称：

  Synthesis, Absorption, and Fluorescence Studies of Coumaryl-Labelled Amino Acids and Dipeptides Linked Via Triazole Ring

  摘要：

  通过铜催化叠氮或炔基化香豆素与炔基或叠氮官能化氨基酸和二肽之间的[3 + 2]环加成反应，合成了基于 4-三唑基、7-羟基-4-三唑基甲基、4-O-三唑基甲基和 7-O-三唑基甲基香豆素标记的氨基酸和二肽的荧光团，产率从良好到极佳。研究了合成共轭物的稳态吸收和荧光特性。通过进一步标记适当的 C 端或 N 端氨基酸，这些基于氨基酸和肽的荧光团的线性延伸成功地证明了它们的化学适用性。

  DOI：

  10.1071/ch14708
• 作为产物：
  描述：

  苄氧羰基-L-丙氨酸 、 3-溴丙炔 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以86%的产率得到Cbz-Ala-OCH2CCH
  参考文献：
  名称：

  Synthesis, Absorption, and Fluorescence Studies of Coumaryl-Labelled Amino Acids and Dipeptides Linked Via Triazole Ring

  摘要：

  通过铜催化叠氮或炔基化香豆素与炔基或叠氮官能化氨基酸和二肽之间的[3 + 2]环加成反应，合成了基于 4-三唑基、7-羟基-4-三唑基甲基、4-O-三唑基甲基和 7-O-三唑基甲基香豆素标记的氨基酸和二肽的荧光团，产率从良好到极佳。研究了合成共轭物的稳态吸收和荧光特性。通过进一步标记适当的 C 端或 N 端氨基酸，这些基于氨基酸和肽的荧光团的线性延伸成功地证明了它们的化学适用性。

  DOI：

  10.1071/ch14708

文献信息

• Conformational behavior of symmetrical and unsymmetrical mono(alkynylpeptide)-tungsten complexes
  作者：Timothy P. Curran、Whitney E. Smith、Peter C. Hendrickson

  DOI：10.1016/j.jorganchem.2012.03.021

  日期：2012.7

  A series of N-protected amino acid alkynylesters were prepared by reaction of the amino acid carboxylate group with either propargyl alcohol (to yield the asymmetric esters 2a-c) or with 1, 4-but-2-yne diol (to yield the symmetric esters 3a-d). The alkynylesters were reacted with W(CO)(3)(dmtc)(2) to yield monoalkyne complexes having the general formula W(CO)(dmtc)(2)(alkynyl ester). The monoalkyne complexes 6a-f were unstable in the presence of oxygen and had to be kept under an inert atmosphere. Analysis of the NMR spectra of the monoalkyne complexes showed that two diastereomers were formed in the synthesis, and that there was rapid rotation of the alkyne about the tungsten center at 23 degrees C and above with both diastereomers. At lower temperatures alkyne rotation is significantly slowed. Symmetric alkynylesters of a dipeptide (4) and tripeptide (5) were also prepared and reacted with W(CO)(3)(dmtc)(2) to yield monoalkyne complexes. The resulting complexes (6g and 6h) also formed two diastereomers and displayed rapid rotation of the alkyne about the tungsten center at 23 degrees C and above, and slow rotation at lower temperatures. The amide NH protons in 6g and 6h were probed by DMSO titration to see if they were involved in intramolecular hydrogen bonds; they were not, which indicates that the peptide portions of 6g and 6h adopt an extended conformation in solution. (C) 2012 Elsevier B. V. All rights reserved.