(5S)-5-methyl-N-prop-2-ynylheptanamide | 862014-97-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (5S)-5-methyl-N-prop-2-ynylheptanamide
• CAS: 862014-97-9
• 化学式: C₁₁H₁₉NO
• 分子量: 181.278
• InChiKey: LVYBJBKUVMOQIN-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (S)-(+)-5-甲基-1-己醇 在 重铬酸吡啶 、 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (5S)-5-methyl-N-prop-2-ynylheptanamide
  参考文献：
  名称：

  Effect of Chiral Substituents on the Secondary Structure of Poly(N-alkynylamides)

  摘要：

  Optically active N-alkynylamides (S)-HC C(CH2)(a)NHCO(CH2)(b)CH(CH3)CH2CH3 (1: a=1, b=0; 2: a=1, b=1; 3: a=1, b=2; 4: a=1, b=3; 5: a=2, b=0; 6: a=2, b=1; 7: a=3, b=0), having several numbers of methylene spacers between the ethynyl group and chiral carbon or amide group, and (S)-HC C(CH2)(2)OCOCH2CH(CH3)CH2CH3 (8) were polymerized with (nbd)Rh+[eta(6)-C6H5B--(C6H5)(3)] to afford the corresponding polymers with moderate molecular weights (Mn = 11000-21000) in 67-99% yields. The H-1 NMR spectra demonstrated that the resulting polymers had stereoregular structures (cis content = 79-100%). CD, UV-vis, and IR spectroscopic studies revealed that the position of the amide group and chiral center strongly affects the pitch and stability of helical structure of the polymers, and intramolecular hydrogen bonding is formed between the amide groups in CHCl3. By comparison with the results of CD measurements and molecular orbital calculation, the sign of Cotton effect and the relationship between the screw sense of poly(N-propargylamides) was elucidated.

  DOI：

  10.1021/ma050313k

文献信息

• Effect of Chiral Substituents on the Secondary Structure of Poly(<i>N</i>-alkynylamides)
  作者：Junichi Tabei、Masashi Shiotsuki、Fumio Sanda、Toshio Masuda

  DOI：10.1021/ma050313k

  日期：2005.7.1

  Optically active N-alkynylamides (S)-HC C(CH2)(a)NHCO(CH2)(b)CH(CH3)CH2CH3 (1: a=1, b=0; 2: a=1, b=1; 3: a=1, b=2; 4: a=1, b=3; 5: a=2, b=0; 6: a=2, b=1; 7: a=3, b=0), having several numbers of methylene spacers between the ethynyl group and chiral carbon or amide group, and (S)-HC C(CH2)(2)OCOCH2CH(CH3)CH2CH3 (8) were polymerized with (nbd)Rh+[eta(6)-C6H5B--(C6H5)(3)] to afford the corresponding polymers with moderate molecular weights (Mn = 11000-21000) in 67-99% yields. The H-1 NMR spectra demonstrated that the resulting polymers had stereoregular structures (cis content = 79-100%). CD, UV-vis, and IR spectroscopic studies revealed that the position of the amide group and chiral center strongly affects the pitch and stability of helical structure of the polymers, and intramolecular hydrogen bonding is formed between the amide groups in CHCl3. By comparison with the results of CD measurements and molecular orbital calculation, the sign of Cotton effect and the relationship between the screw sense of poly(N-propargylamides) was elucidated.