(Boc-Ile-OCH2C)2 | 1376937-27-7

• 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: (Boc-Ile-OCH2C)2
• CAS: 1376937-27-7
• 化学式: C₂₆H₄₄N₂O₈
• 分子量: 512.644
• InChiKey: CCOSDBALTUWFED-MUGJNUQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  36.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  129.26
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (Boc-Ile-OCH2C)2 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 苯甲醚 为溶剂， 反应 6.0h， 生成 (Boc-Val-Ala-Ile-OCH2C)2
  参考文献：
  名称：

  Conformational behavior of symmetrical and unsymmetrical mono(alkynylpeptide)-tungsten complexes

  摘要：

  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.

  DOI：

  10.1016/j.jorganchem.2012.03.021
• 作为产物：
  描述：

  丁炔二醇 、 BOC-L-异亮氨酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 以73%的产率得到(Boc-Ile-OCH2C)2
  参考文献：
  名称：

  Conformational behavior of symmetrical and unsymmetrical mono(alkynylpeptide)-tungsten complexes

  摘要：

  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.

  DOI：

  10.1016/j.jorganchem.2012.03.021