Propyl 2-[hydroxy(naphthalen-2-yl)methyl]prop-2-enoate | 1334831-89-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Propyl 2-[hydroxy(naphthalen-2-yl)methyl]prop-2-enoate
• CAS: 1334831-89-8
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: BSYGCEHYBHHUSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Propyl 2-[hydroxy(naphthalen-2-yl)methyl]prop-2-enoate 、 quinazolin-3-ium-3-yl(tosyl)amide 在 3-[[3,5-双（三氟甲基）苯基]氨基]-4-[[（（1R，2R）-2-（1-哌啶基）环己基]氨基]-3-环丁烯-1,2-二酮 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以82%的产率得到
  参考文献：
  名称：

  通过MBH醇的动力学拆分进行手性方酰胺催化的不对称脱芳香性串联环化反应：三维杂环化合物的高度对映选择性合成†

  摘要：

  在这种交流中，通过温和条件下MBH醇的动力学拆分，实现了未修饰的Morita-Baylis-Hillman醇与偶氮甲亚胺的手性方酸酰胺催化的不对称脱芳香性串联环化反应，得到了药学上有意义的官能化杂双环[3.3.1] ]壬烷衍生物，具有良好的至优异的产率和优异的对映选择性。

  DOI：

  10.1039/c9cc05483a
• 作为产物：
  描述：

  丙烯酸正丙酯 、 2-萘甲醛 在 三乙烯二胺 作用下， 以 丙醇 为溶剂， 反应 144.0h， 以60%的产率得到Propyl 2-[hydroxy(naphthalen-2-yl)methyl]prop-2-enoate
  参考文献：
  名称：

  Synthesis, evaluation against Leishmania amazonensis and cytotoxicity assays in macrophages of sixteen new congeners Morita–Baylis–Hillman adducts

  摘要：

  We report the design, synthesis, in vitro evaluation against Leishmania amazonensis (IC50), cytotoxicity assays in macrophages (CC50), and selectivity index (SI=-CC50/IC50) of sixteen new congeners aromatic Morita-Baylis-Hillman adducts 1-16. The 1-16 were prepared in good to excellent yields (58%-97%) from the "one pot" Morita-Baylis-Hillman Reaction between the aldehydes 29-36 and the acrylates 27 or 28 under DABCO as promoter. The MBHA 2-[Hydroxy(2-nitrophenyl)propyl] propanoate (1, IC50 = 7.52 mu g/mL or 28.38 mu M; CC50 = 35.77 mu g/mL or 134.98 mu M; SI = 4.75) and 2-[Hydroxy(2-[nitrophenyl)hydroxyethyl] propanoate (9, IC50 = 5.48 mu g/mL or 20.52 mu M; CC50 = 29.81 mu g/mL or 111.64c mu M and, SI = 5.43) were the most effective and safe evaluated compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.06.036

文献信息

• A chiral squaramide-catalyzed asymmetric dearomative tandem annulation reaction through a kinetic resolution of MBH alcohols: highly enantioselective synthesis of three-dimensional heterocyclic compounds
  作者：Leijie Zhou、Yuan Zeng、Xing Gao、Qijun Wang、Chang Wang、Bo Wang、Wei Wang、Yongjun Wu、Bing Zheng、Hongchao Guo

  DOI：10.1039/c9cc05483a

  日期：——

  dearomative tandem annulation reaction of unmodified Morita–Baylis–Hillman alcohols with azomethine imines has been achieved through a kinetic resolution of MBH alcohols under mild conditions, giving pharmaceutically interesting functionalized hetero-bicyclo[3.3.1]nonane derivatives in good to excellent yields with excellent enantioselectivities.

  在这种交流中，通过温和条件下MBH醇的动力学拆分，实现了未修饰的Morita-Baylis-Hillman醇与偶氮甲亚胺的手性方酸酰胺催化的不对称脱芳香性串联环化反应，得到了药学上有意义的官能化杂双环[3.3.1] ]壬烷衍生物，具有良好的至优异的产率和优异的对映选择性。
• Synthesis, evaluation against Leishmania amazonensis and cytotoxicity assays in macrophages of sixteen new congeners Morita–Baylis–Hillman adducts
  作者：Fábio P.L. Silva、Priscilla A.C. de Assis、Claudio G.L. Junior、Natália G. de Andrade、Saraghina M.D. da Cunha、Márcia R. Oliveira、Mário L.A.A. Vasconcellos

  DOI：10.1016/j.ejmech.2011.06.036

  日期：2011.9

  We report the design, synthesis, in vitro evaluation against Leishmania amazonensis (IC50), cytotoxicity assays in macrophages (CC50), and selectivity index (SI=-CC50/IC50) of sixteen new congeners aromatic Morita-Baylis-Hillman adducts 1-16. The 1-16 were prepared in good to excellent yields (58%-97%) from the "one pot" Morita-Baylis-Hillman Reaction between the aldehydes 29-36 and the acrylates 27 or 28 under DABCO as promoter. The MBHA 2-[Hydroxy(2-nitrophenyl)propyl] propanoate (1, IC50 = 7.52 mu g/mL or 28.38 mu M; CC50 = 35.77 mu g/mL or 134.98 mu M; SI = 4.75) and 2-[Hydroxy(2-[nitrophenyl)hydroxyethyl] propanoate (9, IC50 = 5.48 mu g/mL or 20.52 mu M; CC50 = 29.81 mu g/mL or 111.64c mu M and, SI = 5.43) were the most effective and safe evaluated compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.