2-氯乙酸萘-2-基 | 26177-06-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-氯乙酸萘-2-基
• 英文名称: 2-naphthyl chloroacetate
• 英文别名: β-Naphthylchloracetat；Naphthalen-2-yl chloroacetate；naphthalen-2-yl 2-chloroacetate
• CAS: 26177-06-0
• 化学式: C₁₂H₉ClO₂
• 分子量: 220.655
• InChiKey: DQHZHTWQJQJIKE-UHFFFAOYSA-N

物化性质

• 保留指数：
  1799

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氯乙酸萘-2-基 在 phosphate buffer 、 N,N,N',N',N'',N'',N''',N'''-octamethyl-2,11,20,29-tetraaza<3.3.3.3>paracyclophanetetrammonium tetrafluoroborate 作用下， 生成 2-萘酚
  参考文献：
  名称：

  Substrate specificity in ester hydrolysis by a new water-soluble heterocyclophane

  摘要：

  DOI：

  10.1021/ja00411a037
• 作为产物：
  描述：

  2-萘酚 在 2,2'-联吡啶 、 三乙胺 、 copper(l) chloride 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 2-氯乙酸萘-2-基
  参考文献：
  名称：

  用于 Hirshfeld 表面分析和 DFT 研究的三氯乙酸苯酯的 CuCl/bpy 促进不寻常的 Z-立体选择性合成

  摘要：

  摘要 三氯甲酯不含适当取代的 CC 键、任何离去基团或在基团 β 位上的 H 原子，这些在其他情况下已知为 ATRA/ATRC、1,2-重排/断裂或简单的 1,2-在惰性 N2 条件下，三氯乙酸苯酯与 2 mol equiv CuCl/bpy 在回流 DCE 或苯中反应，分别发生 H 位移，导致立体选择性合成 Z-2,3-二氯-丁-2-烯二酸二苯酯和/或还原性脱氯副产物的形成。产物的 Z-立体化学通过在 P21/c 对称元素的单斜晶系中结晶的 Z-2,3-二氯-丁-2-烯二酸二萘-1-基酯的 X 射线衍射光谱证实。实验建立的 Z-2 结构的 Hirshfeld 表面分析，3-二氯-丁-2-烯二酸二苯酯揭示了显示氢键和短接触的分子间相互作用。立体化学也使用密度泛函理论在 B3LYP/6-311G(d,p) 理论水平进行计算解释。计算了分子表面上的静电势之间的计算能量、能隙和平衡，这揭示了不太稳定的

  DOI：

  10.1016/j.molstruc.2019.02.018

文献信息

• Magnesium Bistrifluoromethanesulfonimide as a New and Efficient Acylation Catalyst
  作者：Asit K. Chakraborti、Shivani

  DOI：10.1021/jo0605142

  日期：2006.7.1

  room temperature and in short times. Electron-deficient and sterically hindered phenols provided excellent yields. The catalyst was found to be general for acylation with other anhydrides, such as propionic, isobutyric, pivalic, chloroacetic, and benzoic anhydrides. The rate of acylation was influenced by the electronic and steric factors associated with the anhydride. The reaction with less electrophilic

  双三氟甲烷磺酰亚胺镁在无溶剂条件下于室温和短时间内催化酚，醇和硫醇的乙酰化。电子不足和空间受阻的苯酚可提供出色的收率。已发现该催化剂通常可与其他酸酐，如丙酸酐，异丁酸，新戊酸，氯乙酸酐和苯甲酸酐进行酰化反应。酰化的速率受与酸酐相关的电子和空间因素的影响。用较少的亲电子酸酐（例如氯乙酸酐和苯甲酸酐）进行反应需要较高的温度（约80°C）。化学选择性的乙酰化，新戊酸化和苯甲酰化是用酸敏感的醇进行的，没有任何竞争性的脱水/重排。
• Chakraborti, Asit K.; Gulhane, Rajesh; Shivani, Synthesis, 2004, # 1, p. 111 - 115
  作者：Chakraborti, Asit K.、Gulhane, Rajesh、Shivani

  DOI：——

  日期：——
• Designed water-soluble macrocyclic esterases: from nonproductive to productive binding
  作者：Francois Diederich、Gregor Schuermann、Ito Chao

  DOI：10.1021/jo00247a017

  日期：1988.6
• Design, synthesis, biological evaluation and molecular modeling study of new thieno[2,3-d]pyrimidines with anti-proliferative activity on pancreatic cancer cell lines
  作者：Mohamed S.H. Salem、Yasmine M. Abdel Aziz、Mohamed S. Elgawish、Mohamed M. Said、Khaled A.M. Abouzid

  DOI：10.1016/j.bioorg.2019.103472

  日期：2020.1

  Pancreatic cancer is one of the most challenging diseases with seven months only as median survival time due to its poor prognosis. Several enzymes are blamed for the progress of pancreatic cancer especially, platelet-derived growth factor receptors (PDGFRs) this in turn makes them promising targets for its treatment. In this study, twenty eight new compounds based on thieno[2,3-d]pyrimidine scaffold were synthesized as anti-pancreatic cancer agents mimicking the benzofuro[3,2-d]pyrimidine derivative, amuvatinib. Various linkers including amides, esters, ketones, urea and thiourea derivatives were utilized to study their effect on the anti-proliferative activity of these compounds. Most of the tested compounds revealed good cytotoxic activities against pancreatic carcinoma cell line PANG-1. Compound 9d showed the highest cytotoxicity with an IC50 value of 5.4 mu M. Furthermore, 9d showed excellent platelet derived growth factor receptor (PDGFR-alpha) inhibitory activity, with IC50 value 0.155 mu M. Docking study was carried out into PDGFR-alpha active site which showed comparable binding mode to that of FDA approved PDGFR-alpha inhibitor, imatinib. 3D-Quantitative structure activity relationship (QSAR) model was built up with five-featured pharmacophore which could be implemented for emerging effective lead structures. These compounds could serve as a new chemotype for discovering new agents for pancreatic cancer therapy.
• Suzuki, Hitomi; Padmanabhan, Seetharamaiyer; Ogawa, Takuji, Chemistry Letters, 1989, p. 1017 - 1020
  作者：Suzuki, Hitomi、Padmanabhan, Seetharamaiyer、Ogawa, Takuji

  DOI：——

  日期：——