2-溴-6-异丙氧基苯酚 | 350792-40-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-溴-6-异丙氧基苯酚
• 英文名称: 2-Bromo-6-isopropoxyphenol
• 英文别名: 2-bromo-6-propan-2-yloxyphenol
• CAS: 350792-40-4
• 化学式: C₉H₁₁BrO₂
• 分子量: 231.089
• InChiKey: CFQDIVDHBJMOCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2909500000

反应信息

• 作为反应物：
  描述：

  2-溴-6-异丙氧基苯酚 在 正丁基锂 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 19.0h， 生成 (2-tert-butoxy-3-iso-propoxyphenyl)diphenylphosphine
  参考文献：
  名称：

  合成和使用的邻- （支链烷氧基） -叔-butoxybenzenes

  摘要：

  一系列的空间位阻ø - （支链烷氧基） -叔-butoxybenzenes在由于一个新的实用和简单的制备良好的产率被有效地制备ø -叔-butoxyphenol从儿茶酚和异丁烯开始。DMF的使用二-叔丁基缩醛试剂代替异丁烯/ H 2 SO 4（催化量）为ø -叔-butylation是非常方便在的情况下，邻位笨重酚得到相应的叔丁基醚以高收率和纯度。事实证明，这种通用途径是有用的，因为o -di-没有可靠的访问权限t -BuO取代的芳烃。介绍了在拥挤的磷基化合物合成中的应用。

  DOI：

  10.1016/j.tetlet.2012.10.010
• 作为产物：
  描述：

  2-异丙氧基苯酚 在 溴 、 叔丁胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 以85%的产率得到2-溴-6-异丙氧基苯酚
  参考文献：
  名称：

  An Efficient Preparation of 6-Alkoxy-substituted Benzocyclobutenones

  摘要：

  一种高效获取3-烷氧基苯炔的简捷路线已被开发出来，其起始于容易获得的化合物。这使得可以快速获取6-烷氧基苯并环丁烯酮，这些是有价值的合成中间体。

  DOI：

  10.1055/s-2001-12767

文献信息

• An Efficient Preparation of 6-Alkoxy-substituted Benzocyclobutenones
  作者：Christopher J. Bungard、Jonathan C. Morris

  DOI：10.1055/s-2001-12767

  日期：——

  A short, efficient route to 3-alkoxybenzynes has been developed, starting from readily available compounds. This has enabled rapid access to 6-alkoxybenzocyclobutenones, which are valuable synthetic intermediates.

  一种高效获取3-烷氧基苯炔的简捷路线已被开发出来，其起始于容易获得的化合物。这使得可以快速获取6-烷氧基苯并环丁烯酮，这些是有价值的合成中间体。
• 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.
• Synthesis of bulky 1,2-dialkoxy- and 1,2,3-trialkoxy-arenes
  作者：Michel Stephan、Borut Zupančič、Barbara Mohar

  DOI：10.1016/j.tet.2011.06.013

  日期：2011.8

  A large series of bulky 1,2-dialkoxy- and 1,2,3-trialkoxy-benzenes was efficiently prepared via Williamson etherification. Preparation of their contiguous bromine-containing derivatives was also achieved. (C) 2011 Elsevier Ltd. All rights reserved.
• Chemoenzymatic Total Syntheses of Ribisins A, B, and D, Polyoxygenated Benzofuran Derivatives Displaying NGF-Potentiating Properties
  作者：Ping Lan、Martin G. Banwell、Anthony C. Willis

  DOI：10.1021/jo500210k

  日期：2014.4.4

  Total syntheses of the structures, 1, 2, and 4, assigned to the biologically active natural products ribisins A, B, and D, respectively, have been achieved using the microbially derived and enantiomerically pure cis-1,2-dihydrocatechol 5 as starting material. Key steps include Suzuki-Miyaura cross-coupling, intramolecular Mitsunobu, and tandem epoxidation/rearrangement reactions. As a result of these studies, the structures of ribisins A and D have been confirmed while that of congener B was shown to be represented by 31 rather than 2.
• Synthesis and use of ortho-(branched alkoxy)-tert-butoxybenzenes
  作者：Slavko Rast、Michel Stephan、Barbara Mohar

  DOI：10.1016/j.tetlet.2012.10.010

  日期：2012.12

  A series of sterically hindered o-(branched alkoxy)-tert-butoxybenzenes was efficiently prepared in good yields owing to a new practical and simple preparation of o-tert-butoxyphenol starting from catechol and isobutene. Use of DMF di-tert-butyl acetal reagent instead of isobutene/H2SO4 (cat.) for O-tert-butylation was very convenient in case of ortho bulky phenols affording the corresponding tert-butyl

  一系列的空间位阻ø - （支链烷氧基） -叔-butoxybenzenes在由于一个新的实用和简单的制备良好的产率被有效地制备ø -叔-butoxyphenol从儿茶酚和异丁烯开始。DMF的使用二-叔丁基缩醛试剂代替异丁烯/ H 2 SO 4（催化量）为ø -叔-butylation是非常方便在的情况下，邻位笨重酚得到相应的叔丁基醚以高收率和纯度。事实证明，这种通用途径是有用的，因为o -di-没有可靠的访问权限t -BuO取代的芳烃。介绍了在拥挤的磷基化合物合成中的应用。