methyl (2S)-5-[[3-[2-[4-[2-[3-[[(4S)-4-acetamido-5-[[(2S)-1-[[2-methyl-1-[[(2S)-1-[(2-methyl-1-oxo-1-phenacyloxypropan-2-yl)amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-5-oxopentyl]carbamoyl]phenyl]ethynyl]phenyl]ethynyl]benzoyl]amino]-2-[[2-methyl-2-[[(2S)-2-[[2-methyl-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoyl]amino]propanoyl]amino]propanoyl]amino]pentanoate | 1147767-90-5

• 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: methyl (2S)-5-[[3-[2-[4-[2-[3-[[(4S)-4-acetamido-5-[[(2S)-1-[[2-methyl-1-[[(2S)-1-[(2-methyl-1-oxo-1-phenacyloxypropan-2-yl)amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-5-oxopentyl]carbamoyl]phenyl]ethynyl]phenyl]ethynyl]benzoyl]amino]-2-[[2-methyl-2-[[(2S)-2-[[2-methyl-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoyl]amino]propanoyl]amino]propanoyl]amino]pentanoate
• CAS: 1147767-90-5
• 化学式: C₇₈H₁₀₀N₁₂O₁₈
• 分子量: 1493.72
• InChiKey: VEOWAOSNGTXPNM-CQYSTALUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  108
• 可旋转键数：
  41
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  428
• 氢给体数：
  12
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  methyl (2S)-5-[[3-[2-[4-[2-[3-[[(4S)-4-acetamido-5-[[(2S)-1-[[2-methyl-1-[[(2S)-1-[(2-methyl-1-oxo-1-phenacyloxypropan-2-yl)amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-5-oxopentyl]carbamoyl]phenyl]ethynyl]phenyl]ethynyl]benzoyl]amino]-2-[[2-methyl-2-[[(2S)-2-[[2-methyl-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoyl]amino]propanoyl]amino]propanoyl]amino]pentanoate 在 sodium hydroxide 、 苯甲醚 、 三氟乙酸 、 N-羟基-7-氮杂苯并三氮唑 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 以14%的产率得到
  参考文献：
  名称：

  Chirally Twisted Oligo(phenyleneethynylene) by Cyclization with α-Helical Peptide

  摘要：

  A novel cyclic conjugate of a helical decapeptide and oligo(phenyleneethynylene) (OPE), C-OPE10, was synthesized. The conformation and the optical properties of the cyclic conjugate were studied by circular dichroism (CD), absorption, and emission spectroscopies. In the cyclic conjugate, the rotational motion around the molecular axis of the OPE moiety was hindered to take a chirally twisted conformation, which is a distorted form from the coplanar conjugated structure, as revealed by observation of an induced negative Cotton effect of the OPE moiety. Molecular simulation using time dependant-density functional theory indicated a right-handed twist conformation of the OPE moiety for the negative Cotton effect. This conjugate therefore provides a new way to obtain a pi-conjugated compound having, main-chain chirality. The optical properties of the OPE moiety taking the twist conformation in the cyclic conjugate are also discussed in depth.

  DOI：

  10.1021/jo9001905
• 作为产物：
  描述：

  Ac-Orn(Bz(3-I))-Ala-Aib-Ala-Aib-OGly-Ph 、 methyl (2S)-5-[[3-[2-(4-ethynylphenyl)ethynyl]benzoyl]amino]-2-[[2-methyl-2-[[(2S)-2-[[2-methyl-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoyl]amino]propanoyl]amino]propanoyl]amino]pentanoate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以48%的产率得到methyl (2S)-5-[[3-[2-[4-[2-[3-[[(4S)-4-acetamido-5-[[(2S)-1-[[2-methyl-1-[[(2S)-1-[(2-methyl-1-oxo-1-phenacyloxypropan-2-yl)amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-5-oxopentyl]carbamoyl]phenyl]ethynyl]phenyl]ethynyl]benzoyl]amino]-2-[[2-methyl-2-[[(2S)-2-[[2-methyl-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoyl]amino]propanoyl]amino]propanoyl]amino]pentanoate
  参考文献：
  名称：

  Chirally Twisted Oligo(phenyleneethynylene) by Cyclization with α-Helical Peptide

  摘要：

  A novel cyclic conjugate of a helical decapeptide and oligo(phenyleneethynylene) (OPE), C-OPE10, was synthesized. The conformation and the optical properties of the cyclic conjugate were studied by circular dichroism (CD), absorption, and emission spectroscopies. In the cyclic conjugate, the rotational motion around the molecular axis of the OPE moiety was hindered to take a chirally twisted conformation, which is a distorted form from the coplanar conjugated structure, as revealed by observation of an induced negative Cotton effect of the OPE moiety. Molecular simulation using time dependant-density functional theory indicated a right-handed twist conformation of the OPE moiety for the negative Cotton effect. This conjugate therefore provides a new way to obtain a pi-conjugated compound having, main-chain chirality. The optical properties of the OPE moiety taking the twist conformation in the cyclic conjugate are also discussed in depth.

  DOI：

  10.1021/jo9001905

文献信息

• Chirally Twisted Oligo(phenyleneethynylene) by Cyclization with α-Helical Peptide
  作者：Hidenori Nakayama、Shunsaku Kimura

  DOI：10.1021/jo9001905

  日期：2009.5.1

  A novel cyclic conjugate of a helical decapeptide and oligo(phenyleneethynylene) (OPE), C-OPE10, was synthesized. The conformation and the optical properties of the cyclic conjugate were studied by circular dichroism (CD), absorption, and emission spectroscopies. In the cyclic conjugate, the rotational motion around the molecular axis of the OPE moiety was hindered to take a chirally twisted conformation, which is a distorted form from the coplanar conjugated structure, as revealed by observation of an induced negative Cotton effect of the OPE moiety. Molecular simulation using time dependant-density functional theory indicated a right-handed twist conformation of the OPE moiety for the negative Cotton effect. This conjugate therefore provides a new way to obtain a pi-conjugated compound having, main-chain chirality. The optical properties of the OPE moiety taking the twist conformation in the cyclic conjugate are also discussed in depth.