(1S,2S,6R,8S)-4-[(1S)-1-chloro-3-[(4-methoxyphenyl)methoxy]propyl]-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane | 1140737-57-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,2S,6R,8S)-4-[(1S)-1-chloro-3-[(4-methoxyphenyl)methoxy]propyl]-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane
• CAS: 1140737-57-0
• 化学式: C₂₁H₃₀BClO₄
• 分子量: 392.731
• InChiKey: KEYWVWXMNYWIBQ-RFQICNMXSA-N

物化性质

• 沸点：
  457.0±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S,6R,8S)-4-[(1S)-1-chloro-3-[(4-methoxyphenyl)methoxy]propyl]-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane 、 lithium hexamethyldisilazane 以 四氢呋喃 为溶剂， 以90%的产率得到
  参考文献：
  名称：

  Synthesis and evaluation of novel α-amino cyclic boronates as inhibitors of HCV NS3 protease

  摘要：

  We have designed and synthesized a novel series of alpha-amino cyclic boronates and incorporated them successfully in several acyclic templates at the P1 position. These compounds are inhibitors of the HCV NS3 serine protease, and structural studies show that they inhibit the NS3 protease by trapping the Ser-139 hydroxyl group in the active site. Synthetic methodologies and SARs of this series of compounds are described.

  DOI：

  10.1016/j.bmcl.2010.04.129
• 作为产物：
  描述：

  、 (dichloromethyl)lithium 在 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到(1S,2S,6R,8S)-4-[(1S)-1-chloro-3-[(4-methoxyphenyl)methoxy]propyl]-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane
  参考文献：
  名称：

  Synthesis and evaluation of novel α-amino cyclic boronates as inhibitors of HCV NS3 protease

  摘要：

  We have designed and synthesized a novel series of alpha-amino cyclic boronates and incorporated them successfully in several acyclic templates at the P1 position. These compounds are inhibitors of the HCV NS3 serine protease, and structural studies show that they inhibit the NS3 protease by trapping the Ser-139 hydroxyl group in the active site. Synthetic methodologies and SARs of this series of compounds are described.

  DOI：

  10.1016/j.bmcl.2010.04.129

文献信息

• Synthesis and evaluation of novel α-amino cyclic boronates as inhibitors of HCV NS3 protease
  作者：Xianfeng Li、Yong-Kang Zhang、Yang Liu、Charles Z. Ding、Qun Li、Yasheen Zhou、Jacob J. Plattner、Stephen J. Baker、Xuelei Qian、Dazhong Fan、Liang Liao、Zhi-Jie Ni、Gemma V. White、Jackie E. Mordaunt、Linos X. Lazarides、Martin J. Slater、Richard L. Jarvest、Pia Thommes、Malcolm Ellis、Colin M. Edge、Julia A. Hubbard、Don Somers、Paul Rowland、Pamela Nassau、Bill McDowell、Tadeusz J. Skarzynski、Wieslaw M. Kazmierski、Richard M. Grimes、Lois L. Wright、Gary K. Smith、Wuxin Zou、Jon Wright、Lewis E. Pennicott

  DOI：10.1016/j.bmcl.2010.04.129

  日期：2010.6

  We have designed and synthesized a novel series of alpha-amino cyclic boronates and incorporated them successfully in several acyclic templates at the P1 position. These compounds are inhibitors of the HCV NS3 serine protease, and structural studies show that they inhibit the NS3 protease by trapping the Ser-139 hydroxyl group in the active site. Synthetic methodologies and SARs of this series of compounds are described.