(2S,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-methyl-2-propan-2-yl-5,6-dihydro-2H-4,1-benzoxazocin-3-one | 345632-89-5

• 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: (2S,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-methyl-2-propan-2-yl-5,6-dihydro-2H-4,1-benzoxazocin-3-one
• CAS: 345632-89-5
• 化学式: C₂₁H₃₅NO₃Si
• 分子量: 377.599
• InChiKey: KJWQKNLTRURTAA-HKUYNNGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-methyl-2-propan-2-yl-5,6-dihydro-2H-4,1-benzoxazocin-3-one 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.33h， 以71.5%的产率得到(2S,6S)-6-hydroxy-1-methyl-2-propan-2-yl-2,5,6,7-tetrahydro-4,1-benzoxazonin-3-one
  参考文献：
  名称：

  Synthesis, conformation and PKC isozyme surrogate binding of new lactone analogues of benzolactam-V8s

  摘要：

  To investigate the role of the amide hydrogen of benzolactam-V8s (1-3) on protein kinase C (PKC) isozyme binding, new lactone analogues of benzolactam-V8s with hydrophobic side chains at positions 8 and/or 9 (5-8) were synthesized. The PKC binding affinities of 8- and 9-decylbenzolactone-V8 (5,6) were much lower than those of 8- and 9-decylbenzolactam-V8 (2,3), respectively, indicating that the amide hydrogen of benzolactam-V8s plays a critical role in PKC binding. 8-Decylbenzolactam-V8 (2) showed lower binding affinities to all PKC isozymes compared with those of 9-decylbenzolactam-V8 (3). The binding affinities of 8-substituted benzolactones (5,7,8) were also lower than those of 9-decylbenzolactone-V8 (6), but their PKC isozyme selectivity was higher than those of 2, 3 and 6. 8-Decybenzolactone-V8 (5) exhibited the most significant eta-C1B selectivity among the four benzolactones (5-8) synthesized in this study. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00099-6
• 作为产物：
  描述：

  3-(2-Nitrophenyl)propane-1,2-diol 在 palladium on activated charcoal 咪唑 、 2,6-二甲基吡啶 、 TEA 、 氢气 、 sodium cyanoborohydride 、 1-羟基苯并三唑 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (2S,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-methyl-2-propan-2-yl-5,6-dihydro-2H-4,1-benzoxazocin-3-one
  参考文献：
  名称：

  The amide hydrogen of (−)-indolactam-V and benzolactam-V8’s plays a critical role in protein kinase c binding and tumor-promoting activities

  摘要：

  To investigate the role of the amide hydrogen of (-)-indolactam-V (1) and benzolactam-V8's on protein kinase C (PKC) binding and tumor promotion, 8-decylbenzolactone-V8 (6), a new lactone analogue of 8-decylbenzolactam-V8 (4), was synthesized from 2-nitrophenylpyruvic acid (7) in 11 steps. The PKC binding ability and tumor-promoting activities in vitro of 6 were much lower than those of 1 and 4, suggesting that the amide hydrogen of 1 and benzolactam-V8's plays a critical role in tumor promotion. However, it is noteworthy that 6 showed significant selectivity in the PKC isozyme surrogate binding. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(01)00047-6