(1R)-1-amino-2-(4-methoxyphenyl)-ethylboronic acid (+)-pinanediol ester trifluoroacetate | 1158974-86-7

• 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: (1R)-1-amino-2-(4-methoxyphenyl)-ethylboronic acid (+)-pinanediol ester trifluoroacetate
• CAS: 1158974-86-7
• 化学式: C₂HF₃O₂*C₁₉H₂₈BNO₃
• 分子量: 443.271
• InChiKey: OAFTVTDSWUFVNJ-MFSCCJOXSA-N

物化性质

• 熔点：
  116-118 °C(Solvent: Hexane)

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  91.01
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1R)-1-amino-2-(4-methoxyphenyl)-ethylboronic acid (+)-pinanediol ester trifluoroacetate 在 盐酸 、 异丁基硼酸 、 水 作用下， 以 正己烷 为溶剂， 生成 (R)-(1-Amino-2-(4-methoxyphenyl)ethyl)boronic acid hydrochloride
  参考文献：
  名称：

  Synthesis of boronic acid derivatives of tyropeptin: Proteasome inhibitors

  摘要：

  Boronic acid derivatives of tyropeptin were synthesized with TP-110 as the lead compound. Due to the lability of the aminoboronic acid moiety, careful design of the deprotection and coupling sequence was required. Liquid-liquid partition chromatography was found to be a powerful tool for purification of compounds of this class. The obtained derivatives showed potent inhibitory activities against the human 20S proteasome in vitro. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.117
• 作为产物：
  描述：

  N-((R)-2-(4-methoxyphenyl)-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)ethyl)-1,1,1-trimethyl-N-(trimethylsilyl)silanamine 、 三氟乙酸 反应 1.0h， 以95%的产率得到(1R)-1-amino-2-(4-methoxyphenyl)-ethylboronic acid (+)-pinanediol ester trifluoroacetate
  参考文献：
  名称：

  Synthesis of boronic acid derivatives of tyropeptin: Proteasome inhibitors

  摘要：

  Boronic acid derivatives of tyropeptin were synthesized with TP-110 as the lead compound. Due to the lability of the aminoboronic acid moiety, careful design of the deprotection and coupling sequence was required. Liquid-liquid partition chromatography was found to be a powerful tool for purification of compounds of this class. The obtained derivatives showed potent inhibitory activities against the human 20S proteasome in vitro. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.117