1-[phenyl(phenylamino)methyl] naphthalen-2-ol | 351345-54-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[phenyl(phenylamino)methyl] naphthalen-2-ol
• 英文别名: 1-[Anilino(phenyl)methyl]naphthalen-2-ol
• CAS: 351345-54-5
• 化学式: C₂₃H₁₉NO
• 分子量: 325.41
• InChiKey: DEHFLWZOQVZVII-UHFFFAOYSA-N

物化性质

• 熔点：
  128-130 °C
• 沸点：
  520.9±35.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[phenyl(phenylamino)methyl] naphthalen-2-ol 在 乙醇 、 溶剂黄146 作用下， 生成 2,3-dihydro-1,2,3-triphenyl-1H-naphth<1,2-e><1,3>oxazine
  参考文献：
  名称：

  Betti, Gazzetta Chimica Italiana, 1901, vol. 31 II, p. 197

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-dihydro-1,2,3-triphenyl-1H-naphth<1,2-e><1,3>oxazine 在 盐酸 、 水 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 3.0h， 以24.4 g的产率得到1-[phenyl(phenylamino)methyl] naphthalen-2-ol
  参考文献：
  名称：

  Periasamy, Mariappan; Anwar, Shaik; Reddy, Meda Narsi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 9, p. 1261 - 1273

  摘要：

  DOI：

文献信息

• Synthesis of 1-(α-aminoalkyl)-2-naphthol and α-aminonitrile derivatives with molybdenum Schiff base complex covalently bonded on silica-coated magnetic nanoparticles and DNA interaction study of one type of derivatives using computational and spectroscopic methods
  作者：Jamshid Rakhtshah、Behrouz Shaabani、Sadegh Salehzadeh、Neda Hosseinpour Moghadam

  DOI：10.1016/j.bioorg.2019.01.022

  日期：2019.4

  1-(α-aminoalkyl)-2-naphthol derivatives have been demonstrated under mild condition with short reaction times, high yields and TON values up to 570. To survey the generality of the procedure, we studied the synthesis of α-aminonitrile derivatives with different aldehydes, trimethylsilyl cyanide (TMSCN) and aniline under the same conditions. Additionally, binding interaction of 1-(phenyl(pyridin-2-ylamino)methyl)naphthalen-2-ol

  开发了一种固定在具有核-壳结构的磁性氧化铁纳米粒子上的空气和水分稳定的Schiff钼钼配合物，用作新型非均相催化剂。纳米材料的表面，结构和磁性特征通过傅里叶变换红外（FT-IR）光谱，X射线粉末衍射（XRD），振动样品磁法（VSM），扫描电子显微镜（SEM），能量色散X表征射线（EDX）和电感耦合等离子体原子发射光谱（ICP-AES）。从应用的角度来看，已证明在温和条件下以短时间，高收率和TON值高达570的条件合成了用于合成1-（α-氨基烷基）-2-萘酚衍生物的超声辅助一锅多组分方案。为了调查程序的普遍性，我们研究了在相同条件下用不同的醛，三甲基甲硅烷基氰化物（TMSCN）和苯胺合成α-氨基腈衍生物的方法。另外，已经通过分子模型研究研究了1-（苯基（吡啶-2-基氨基）甲基）萘-2-醇（AMAN-1）与各种类型的刚性DNA和HSA的结合相互作用。在生理条件下的体外研究表明，所需的衍生物通过
• One-pot three-component Mannich-type reaction catalyzed by trifluoromethanesulfonic acid in water
  作者：Gang Li、Hankui Wu、Zhiyong Wang、Xianli Wang

  DOI：10.1134/s0023158411010113

  日期：2011.2

  One-pot three-component Mannich-type reaction of ketones, aldehydes and amines was efficiently catalyzed by liquid trifluoromethanesulfonic acid in water at ambient temperature. The high yield of corresponding β-amino ketones compounds were achieved. The proposed method is mild, green, simple and efficient.

  在环境温度下，液体三氟甲磺酸在水中能有效地催化酮，醛和胺的一锅三组分曼尼希型反应。实现了高产率的相应β-氨基酮化合物。该方法温和，绿色，简单，有效。
• Zn(OAc)2•2H2O-Catalyzed Betti Base Synthesis under Solvent-free Conditions
  作者：M. Mujahid Alam、Hari B. Bollikolla、Ravi Varala

  DOI：10.2174/1570178618666210616155257

  日期：2022.1

  :Zn(OAc)2•2H2O-catalyzed one-pot multicomponent reaction of Betti bases using β-naphthol, aldehydes, and amines, under neat conditions in moderate to excellent yields (68-96%) is reported in this study. This synthetic protocol offers several advantages, such as operationalsimplicity, shorter reaction period, high yields, and easy work-up procedures.

  本研究报道了：Zn(OAc)2•2H2O 催化 Betti 碱使用 β-萘酚、醛和胺的一锅多组分反应，在纯条件下以中等至优异的产率 (68-96%)。这种合成方案具有几个优点，例如操作简单、反应时间短、产率高和后处理程序简单。
• C–H functionalization of aromatic amines for azidation catalyzed by Betti base coordinated copper(<scp>ii</scp>) complexes under ultrasonication
  作者：Premkumar G.、Toka Swu、Richa Gupta、Kothandaraman R.

  DOI：10.1039/d3nj01927f

  日期：——

  Five new Betti base copper(II) complexes (C1–C5) are successfully synthesized and characterized spectroscopically. X-ray diffraction analysis confirmed the square planar geometry of complex C4. Their catalytic application in the C–H functionalization of aromatic amines for azidation was successfully demonstrated under ultrasonication. Complex C5 showed better catalytic activity and produced 2-azidoaniline

  成功合成了五种新的 Betti 基铜 ( II ) 配合物 ( C1–C5 ) 并进行了光谱表征。X射线衍射分析证实了配合物C4的方形平面几何形状。它们在超声波作用下成功地证明了它们在芳香胺 C-H 官能化叠氮化中的催化应用。复合C5显示出更好的催化活性，2-叠氮基苯胺的收率达到85%，高于现有方法；它的性能也比商业催化剂更好，效率更高。该反应涉及较低的催化负载和较短的反应时间。进行对照实验来预测反应途径。基于这些结果，提出了一种涉及自由基途径并伴有单电子转移机制的合理机制。并对不同芳香胺的底物范围进行了研究，成功得到了相应的叠氮化物。所有合成的叠氮化物均用于点击反应以获得各自的三唑。
• 8-Hydroxyquinoline-based inhibitors of the Rce1 protease disrupt Ras membrane localization in human cells
  作者：Idrees Mohammed、Shahienaz E. Hampton、Louise Ashall、Emily R. Hildebrandt、Robert A. Kutlik、Surya P. Manandhar、Brandon J. Floyd、Haley E. Smith、Jonathan K. Dozier、Mark D. Distefano、Walter K. Schmidt、Timothy M. Dore

  DOI：10.1016/j.bmc.2015.11.043

  日期：2016.1

  Ras converting enzyme 1 (Rce1) is an endoprotease that catalyzes processing of the C-terminus of Ras protein by removing -aaX from the CaaX motif. The activity of Rce1 is crucial for proper localization of Ras to the plasma membrane where it functions. Ras is responsible for transmitting signals related to cell proliferation, cell cycle progression, and apoptosis. The disregulation of these pathways due to constitutively active oncogenic Ras can ultimately lead to cancer. Ras, its effectors and regulators, and the enzymes that are involved in its maturation process are all targets for anti-cancer therapeutics. Key enzymes required for Ras maturation and localization are the farnesyltransferase (FTase), Rce1, and isoprenylcysteine carboxyl methyltransferase (ICMT). Among these proteins, the physiological role of Rce1 in regulating Ras and other CaaX proteins has not been fully explored. Small-molecule inhibitors of Rce1 could be useful as chemical biology tools to understand further the downstream impact of Rce1 on Ras function and serve as potential leads for cancer therapeutics. Structure-activity relationship (SAR) analysis of a previously reported Rce1 inhibitor, NSC1011, has been performed to generate a new library of Rce1 inhibitors. The new inhibitors caused a reduction in Rce1 in vitro activity, exhibited low cell toxicity, and induced mislocalization of EGFP-Ras from the plasma membrane in human colon carcinoma cells giving rise to a phenotype similar to that observed with siRNA knockdowns of Rce1 expression. Several of the new inhibitors were more effective at mislocalizing K-Ras compared to a potent farnesyltransferase inhibitor (FTI), which is significant because of the preponderance of K-Ras mutations in cancer. (C) 2015 Elsevier Ltd. All rights reserved.