4-(2-苯基-1,3-恶唑-5-基)苯酚 | 103656-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(2-苯基-1,3-恶唑-5-基)苯酚
• 英文名称: 4-(2-phenyloxazol-5-yl)phenol
• 英文别名: 4-(2-phenyl-1,3-oxazol-5-yl)phenol
• CAS: 103656-71-9
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: QZQUIKWDGDUNEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  香叶基溴 、 4-(2-苯基-1,3-恶唑-5-基)苯酚 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以45%的产率得到(E)-5-(4-[(3,7-dimethylocta-2,6-dien-1-yl)oxy]phenyl)-2-phenyloxazole
  参考文献：
  名称：

  Structure–Activity Relationships of New Natural Product-Based Diaryloxazoles with Selective Activity against Androgen Receptor-Positive Breast Cancer Cells

  摘要：

  Targeted therapies for ER+/PR+ and HER2-amplified breast cancers have improved patient survival, but there are no therapies for triple negative breast cancers (TNBC) that lack expression of estrogen and progesterone receptors (ER/PR), or amplification or overexpression of HER2. Gene expression profiling of TNBC has identified molecular subtypes and representative cell lines. An extract of the Texas native plant Amyris texana was found to have selective activity against MDA-MB-453 cells, a model of the luminal androgen receptor (LAR) subtype of TNBC. Bioassay-guided fractionation identified two oxazole natural products with selective activity against this cell line. Conducted analog synthesis and structure activity relationship studies provided analogs with more potent and selective activity against two LAR. subtype cell line models, culminating in the discovery of compound 30 (CIDD-0067106). Lead compounds discovered have potent and selective antiproliferative activities, and mechanisms of action studies show they inhibit the activity of the mTORC1 pathway.

  DOI：

  10.1021/acs.jmedchem.7b01228
• 作为产物：
  描述：

  5-(4-methoxyphenyl)-2-phenyl-1,3-oxazole 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以91%的产率得到4-(2-苯基-1,3-恶唑-5-基)苯酚
  参考文献：
  名称：

  Structure–Activity Relationships of New Natural Product-Based Diaryloxazoles with Selective Activity against Androgen Receptor-Positive Breast Cancer Cells

  摘要：

  Targeted therapies for ER+/PR+ and HER2-amplified breast cancers have improved patient survival, but there are no therapies for triple negative breast cancers (TNBC) that lack expression of estrogen and progesterone receptors (ER/PR), or amplification or overexpression of HER2. Gene expression profiling of TNBC has identified molecular subtypes and representative cell lines. An extract of the Texas native plant Amyris texana was found to have selective activity against MDA-MB-453 cells, a model of the luminal androgen receptor (LAR) subtype of TNBC. Bioassay-guided fractionation identified two oxazole natural products with selective activity against this cell line. Conducted analog synthesis and structure activity relationship studies provided analogs with more potent and selective activity against two LAR. subtype cell line models, culminating in the discovery of compound 30 (CIDD-0067106). Lead compounds discovered have potent and selective antiproliferative activities, and mechanisms of action studies show they inhibit the activity of the mTORC1 pathway.

  DOI：

  10.1021/acs.jmedchem.7b01228

文献信息

• TBHP/I₂-Mediated Domino Oxidative Cyclization for One-Pot Synthesis of Polysubstituted Oxazoles
  作者：Huanfeng Jiang、Huawen Huang、Hua Cao、Chaorong Qi

  DOI：10.1021/ol1023085

  日期：2010.12.3

  A facile type of one-pot, transition-metal-free domino process was developed for the synthesis of oxazoles. Thus, a variety of polysubstituted oxazoles were easily synthesized via t-BuOOH/I2-mediated domino oxidative cyclization from readily available starting materials under mild conditions.

  开发了一种简便的单罐，无过渡金属的多米诺骨牌工艺，用于合成恶唑。因此，通过t- BuOOH / I 2介导的多米诺氧化环化反应可以容易地在温和条件下从容易获得的起始原料合成多种多取代的恶唑。
• Efficient Synthesis of Resin-Bound α-TMSdiazoketones and Their Use in Solid-Phase Organic Synthesis
  作者：Yasuyoshi Iso、Hirohisa Shindo、Hiroshi Hamana

  DOI：10.1016/s0040-4020(00)00440-3

  日期：2000.7

  a solid support could be simply and efficiently prepared by reaction of the corresponding resin-bound acid chlorides with excess TMSdiazomethane, without any bases. These α-TMSdiazoketones were used via carbenes or carbenoids for a variety of solid-phase reactions. These useful solid-phase reactions allow efficient construction of diverse compound libraries by use of combinatorial chemistry, due to

  通过使相应的树脂结合的酰氯与过量的TMS重氮甲烷在没有任何碱的情况下反应，可以简单而有效地制备固相载体上的α-TMS二重氮酮。这些α-TMS二氮杂酮通过碳烯或类胡萝卜素用于各种固相反应。这些有效的固相反应可通过组合化学有效地构建各种化合物库，这是由于羧甲基或类胡萝卜素具有很高的反应性和广泛的用途。
• Metal-free dual sp3 C–H functionalization: I2-promoted domino oxidative cyclization to construct 2,5-disubstituted oxazoles
  作者：Qing-He Gao、Zhuan Fei、Yan-Ping Zhu、Mi Lian、Feng-Cheng Jia、Mei-Cai Liu、Neng-Fang She、An-Xin Wu

  DOI：10.1016/j.tet.2012.10.072

  日期：2013.1

  An I-2-promoted sp(3) C-H functionalization has been developed for the synthesis of 2,5-disubstituted oxazoles from easily available methyl ketones and benzylamines without any metal and peroxide catalyst. This domino oxidative cyclization process involves the cleavage of C H bond and the formation of C-N, C-O bonds. (C) 2012 Elsevier Ltd. All rights reserved.
• Jacobsen, Noel W.; Philippides, Athena, Australian Journal of Chemistry, 1985, vol. 38, # 9, p. 1335 - 1338
  作者：Jacobsen, Noel W.、Philippides, Athena

  DOI：——

  日期：——
• JACOBSEN, N. W.;PHILIPPIDES, A., AUSTRAL. J. CHEM., 1985, 38, N 9, 1315-1338
  作者：JACOBSEN, N. W.、PHILIPPIDES, A.

  DOI：——

  日期：——