3-methoxy-2-isopropoxyphenylboronic acid | 586963-58-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-methoxy-2-isopropoxyphenylboronic acid
• 英文别名: (2-Isopropoxy-3-methoxyphenyl)boronic acid；(3-methoxy-2-propan-2-yloxyphenyl)boronic acid
• CAS: 586963-58-8
• 化学式: C₁₀H₁₅BO₄
• 分子量: 210.038
• InChiKey: ZVPNXIPBRLMAPX-UHFFFAOYSA-N

物化性质

• 熔点：
  77-79 °C
• 沸点：
  362.1±52.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.16
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methoxy-2-isopropoxyphenylboronic acid 在 咪唑 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 偶氮二异丁腈 、 偶氮二甲酸二异丙酯 、 palladium 10% on activated carbon 、 四丁基氟化铵 、 氢气 、 溴 、 三乙基硼氢化锂 、 sodium carbonate 、 potassium carbonate 、 戴斯-马丁氧化剂 、 溶剂黄146 、 三苯基膦 、 三甲氧基磷 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 甲苯 、 苯 为溶剂， 反应 336.5h， 生成 2-[(5aR,7R,9aR)-7-hydroxy-4-methoxy-6,7-dihydro-5aH-dibenzofuran-9a-yl]-N-methylacetamide
  参考文献：
  名称：

  A First Generation Chemoenzymatic Synthesis of (+)-Galanthamine

  摘要：

  以容易获得且对映体纯度高的代谢物 2 为起始原料，实现了(+)-加兰他敏[(+)-1]的全合成。与目标物 1 相关的季碳中心（C8a）是通过埃申莫瑟-克莱森重排反应生成的。

  DOI：

  10.1071/ch10201
• 作为产物：
  描述：

  2-溴-6-甲氧基苯酚 在 正丁基锂 、 硼酸三异丙酯 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 3-methoxy-2-isopropoxyphenylboronic acid
  参考文献：
  名称：

  A First Generation Chemoenzymatic Synthesis of (+)-Galanthamine

  摘要：

  以容易获得且对映体纯度高的代谢物 2 为起始原料，实现了(+)-加兰他敏[(+)-1]的全合成。与目标物 1 相关的季碳中心（C8a）是通过埃申莫瑟-克莱森重排反应生成的。

  DOI：

  10.1071/ch10201

文献信息

• Development of Natural Product-Derived Receptor Tyrosine Kinase Inhibitors Based on Conservation of Protein Domain Fold
  作者：Lars Kissau、Petra Stahl、Ralph Mazitschek、Athannasios Giannis、Herbert Waldmann

  DOI：10.1021/jm0307943

  日期：2003.7.1

  Receptor tyrosine kinases (RTKs) such as Tie-2, IGF1R, Her-2/Neu, EGFR, and VEGFR1-3 play crucial roles in the control of cell growth and differentiation. Inhibition of such RTKs has become a major focus of current anticancer drug development, and therefore the discovery of new classes of inhibitors for these signal-transducing proteins is of prime importance. We have recently proposed a novel concept for improving the hit-finding process by employing natural products as biologically validated starting points in structural space for compound library development. In this concept, natural products are regarded as evolutionary chosen ligands for protein domains which are structurally conserved yet genetically mobile. Here we report on the discovery of novel and highly selective VEGFR-2 and -3, Tie-2, and IGF1R inhibitors derived from the naturally occurring Her-2/Neu kinase inhibitor nakijiquinone C and developed on the basis of this concept. Based on the structure of the natural product, a small library (74 members) was synthesized and investigated for inhibition of kinases with highly similar ATP-binding domains. The library yielded inhibitors with IC(50)s in the low micromolar range with high frequency (7 out of 74). In particular, four inhibitors of Tie-2 were found, a kinase critically involved in the formation of new blood vessels from preexisting ones (angiogenesis) and believed to be a new promising target in antitumor therapy. These results support the "domain concept". To advance the development of improved inhibitors, extensive molecular modeling studies were undertaken, including the construction of new homology models for VEGFR-2 and Tie-2. These studies revealed residues in the kinase structure which are crucial to the development of tailor-made receptor tyrosine kinase inhibitors.
• A First Generation Chemoenzymatic Synthesis of (+)-Galanthamine
  作者：Martin G. Banwell、Xinghua Ma、Ochitha P. Karunaratne、Anthony C. Willis

  DOI：10.1071/ch10201

  日期：——

  A total synthesis of (+)-galanthamine [(+)-1] has been achieved using the readily available and enantiomerically pure metabolite 2 as starting material. The quaternary carbon centre (C8a) associated with target 1 was constructed using the Eschenmoser–Claisen rearrangement reaction.

  以容易获得且对映体纯度高的代谢物 2 为起始原料，实现了(+)-加兰他敏[(+)-1]的全合成。与目标物 1 相关的季碳中心（C8a）是通过埃申莫瑟-克莱森重排反应生成的。