12-oxo-1,15-pentadecanlactam

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: 12-oxo-1,15-pentadecanlactam
• 英文别名: 12-Oxo-15-pentadecanlactam；12-oxopentadecanlactam；Azacyclohexadecane-2,13-dione
• 化学式: C₁₅H₂₇NO₂
• 分子量: 253.385
• InChiKey: REIOUBQICPJLJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  12-oxo-1,15-pentadecanlactam 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以89%的产率得到12-hydroxy-1,15-pentadecanlactam
  参考文献：
  名称：

  Resolution of racemic 12-hydroxyl-1,15-pentadecanlactam using d-glucose derivative as a chiral auxiliary

  摘要：

  Racemic 12-hydroxyl-1,15-pentadecanlactam 2 was resolved using glucose as a chiral auxiliary for the first time. Both the (R)- and (S)-isomers were obtained in high enantiomeric excesses (>99% by HPLC). The absolute configuration of (+)-2b and (-)-2a was determined by Horeau's method and a modified Mosher's method. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.007
• 作为产物：
  描述：

  12-Nitro-15-pentadecanlactam 在 Sodium tetraborate decahydrate 、 potassium permanganate 、 lithium methanolate 作用下， 以 甲醇 为溶剂， 以2%的产率得到12-oxo-1,15-pentadecanlactam
  参考文献：
  名称：

  SYNTHESE macrocyclischer内酰胺AUS Ketonen第三人以Ringerweiterung †

  摘要：

  扩环反应由酮合成大环内酰胺

  DOI：

  10.1002/hlca.19850680222

文献信息

• Synthesis and Fungicidal Activity of Macrolactams and Macrolactones with an Oxime Ether Side Chain
  作者：Jia-Xing Huang、Yue-Mei Jia、Xiao-Mei Liang、Wei-Juan Zhu、Jian-Jun Zhang、Yan-Hong Dong、Hui-Zu Yuan、Shu-Hua Qi、Jin-Ping Wu、Fu-Heng Chen、Dao-Quan Wang

  DOI：10.1021/jf072733+

  日期：2007.12.1

  Three series of novel macrolactams and macrolactones - 12-alkoxyimino-tetradecanlactam, 12-alkoxyiminopentadecanlactam, and 12-alkoxyiminodecanlactone derivatives (7A, 7B, and 7C) - were synthesized from corresponding 12-oxomacrolactams and 12-oxomacrolactone. Their structures were confirmed by H-1 NMR and elemental analysis. The Z and E isomers of 7A and 7B were separated, and their configurations were determined by H-1 NMR. These compounds showed fair to excellent fungicidal activities against Rhizoctonia solani Kuhn. It is interesting that the Z and E isomers of most of the compounds have quite different fungicidal activities. The fact that the compounds have a gradual increase of fungicidal activity in the order of 7A, 7C, and 7B indicated that the macrocyclic derivatives with a hydrogen-bonding acceptor (=N-O-) and a hydrogen-bonding donor (-CONH-) on the ring, and a three methylenes distance (CH2CH2CH2) between these two functional groups, exhibited the best fungicidal activity. The bioassay also showed that 7B not only has good fungicidal activity but also may have a broad spectrum of fungicidal activities.
• Primary Study on Mode of Action for Macrocyclic Fungicide Candidates (<b>7B3</b>, <b>D1</b>) against Rhizoctonia solani Kühn
  作者：Xiaojing Yan、Xiaomei Liang、Shuhui Jin、Jinping Lv、Chunxin Yu、Wenyan Qi、Baoju Li、Huizhu Yuan、Shuhua Qi、Yanxia Shi、Jingping Wu、Fuheng Chen、Daoquan Wang

  DOI：10.1021/jf9037369

  日期：2010.3.10

  A novel macrolactam fungicide candidate (7B3) and a novel aza-macrolactone fungicide candidate (D1) were designed and synthesized, and the bioassay showed that both displayed excellent fungicidal activity against Rhizoctonia solani Kuhn. To elucidate the biochemical mode of action of the two compounds against R. solani and illustrate the similarities and differences of action mechanism resulting from subtle differences in structure of the two compounds, the effects of the two compounds on the ultrastructure of hyphae, electrolyte leakage, and respiration of mycelia cell suspension caused by 7B3 or D1 were studied. The results showed that the two compounds had very similar modes of action. Both induced irregular swelling of hyphae, vacuolation of cytoplasm, and thickening of cell wall. The conductivity of mycelia cell suspension increased in the presence of 7B3 or D1, which indicated that the two compounds had a similar effect on cell membrane permeability. In addition, both 7B3 and D1 were insufficient in inhibiting the respiration of mycelia.
• WAELCHLI, R.;BIENZ, S.;HENSE, M., HELV. CHIM. ACTA, 1985, 68, N 2, 484-492
  作者：WAELCHLI, R.、BIENZ, S.、HENSE, M.

  DOI：——

  日期：——
• Resolution of racemic 12-hydroxyl-1,15-pentadecanlactam using d-glucose derivative as a chiral auxiliary
  作者：Chuan-Jin Hou、Xiao-Mei Liang、Jing-Ping Wu、Jia-Xing Huang、Jian-Jun Zhang、Dao-Quan Wang

  DOI：10.1016/j.tetasy.2008.01.007

  日期：2008.2

  Racemic 12-hydroxyl-1,15-pentadecanlactam 2 was resolved using glucose as a chiral auxiliary for the first time. Both the (R)- and (S)-isomers were obtained in high enantiomeric excesses (>99% by HPLC). The absolute configuration of (+)-2b and (-)-2a was determined by Horeau's method and a modified Mosher's method. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthese macrocyclischer Lactame aus Ketonen durch Ringerweiterung
  作者：Rudolf Wälchli、Stefan Bienz、Manfred Hesse

  DOI：10.1002/hlca.19850680222

  日期：1985.3.27

  Synthesis of Macrocyclic Lactams from Ketones by Ring Enlargement Reaction

  扩环反应由酮合成大环内酰胺