methyl (E)-3-[3-(dimethylamino)phenyl]acrylate | 1292323-52-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (E)-3-[3-(dimethylamino)phenyl]acrylate
• 英文别名: (E)-methyl 3-(3-(dimethylamino)phenyl)acrylate；methyl (E)-3-[3-(dimethylamino)phenyl]prop-2-enoate
• CAS: 1292323-52-4
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: DPZDGFARPFOWNB-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-[3-(dimethylamino)phenyl]acrylate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-3-(3-(dimethylamino)phenyl)prop-2-en-1-ol
  参考文献：
  名称：

  Emission Wavelength Prediction of a Full-Color-Tunable Fluorescent Core Skeleton, 9-Aryl-1,2-dihydropyrrolo[3,4-b]indolizin-3-one

  摘要：

  In this paper we report on a novel fluorescent core skeleton, 9-aryl-1,2-dihydropyrrolo[3,4-b]indolizin-3-one, which we named Seoul-Fluor, having tunable and predictable photophysical properties. Using a concise and practical one-pot synthetic procedure, a 68-member library of new fluorescent compounds was synthesized with diverse substituents. In Seoul-Fluor, the electronic characteristics of the substituents, as well as their positional changes, have a close correlation with their photophysical properties. The systematic perturbation of electronic densities on the specific positions of Seoul-Fluor, guided with the Hammett constant, allows emission wavelength tunability covering the full color range. On the basis of these observations and a computational analysis, we extracted a simple first-order correlation of photophysical properties with the theoretical calculation and accurately predicted the emission wavelength of Seoul-Fluors through the rational design. In this study, we clearly demonstrate that Seoul-Fluor can provide a powerful gateway for the generation of desired fluorescent probes without the need for a tiresome synthesis and trial-and-error process.

  DOI：

  10.1021/ja110766a
• 作为产物：
  描述：

  3-(二甲氨基)苯甲基醇 在 sodium hydride 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 methyl (E)-3-[3-(dimethylamino)phenyl]acrylate
  参考文献：
  名称：

  Emission Wavelength Prediction of a Full-Color-Tunable Fluorescent Core Skeleton, 9-Aryl-1,2-dihydropyrrolo[3,4-b]indolizin-3-one

  摘要：

  In this paper we report on a novel fluorescent core skeleton, 9-aryl-1,2-dihydropyrrolo[3,4-b]indolizin-3-one, which we named Seoul-Fluor, having tunable and predictable photophysical properties. Using a concise and practical one-pot synthetic procedure, a 68-member library of new fluorescent compounds was synthesized with diverse substituents. In Seoul-Fluor, the electronic characteristics of the substituents, as well as their positional changes, have a close correlation with their photophysical properties. The systematic perturbation of electronic densities on the specific positions of Seoul-Fluor, guided with the Hammett constant, allows emission wavelength tunability covering the full color range. On the basis of these observations and a computational analysis, we extracted a simple first-order correlation of photophysical properties with the theoretical calculation and accurately predicted the emission wavelength of Seoul-Fluors through the rational design. In this study, we clearly demonstrate that Seoul-Fluor can provide a powerful gateway for the generation of desired fluorescent probes without the need for a tiresome synthesis and trial-and-error process.

  DOI：

  10.1021/ja110766a

文献信息

• Lewis Base Activation of Silyl Acetals: Iridium-Catalyzed Reductive Horner–Wadsworth–Emmons Olefination
  作者：Udaya Sree Dakarapu、Apparao Bokka、Parham Asgari、Gabriela Trog、Yuanda Hua、Hiep H. Nguyen、Nawal Rahman、Junha Jeon

  DOI：10.1021/acs.orglett.5b02901

  日期：2015.12.4

  A Lewis base promoted deprotonative pronucleophile addition to silyl acetals has been developed and applied to the iridium-catalyzed reductive Horner–Wadsworth–Emmons (HWE) olefination of esters and the chemoselective reduction of the resulting enoates. Lewis base activation of silyl acetals generates putative pentacoordinate silicate acetals, which fragment into aldehydes, silanes, and alkoxides in

  已经开发了路易斯碱促进的除甲硅烷基乙缩醛外的质子化原核亲核试剂，并将其应用于铱催化的酯的霍纳-沃兹沃斯-埃蒙斯（HWE）还原性烯化反应以及所得烯酸酯的化学选择性还原。甲硅烷基乙缩醛的路易斯碱活化生成推定的五配位硅酸酯乙缩醛，其原位分解为醛，硅烷和醇盐。膦酸酯的随后去质子化金属化，然后与醛进行HWE，提供烯酸酯。该操作方便，机制独特的方案可在室温下在单个容器中将传统上具有挑战性的芳基，烯基和炔基酯转化为均一的烯酸酯。
• HONG, PANGBU;MISE, TAKAYA;YAMAZAKI, HIROSHI, J. CHEM. SOC. JAP., CHEM. AND IND. CHEM., 1985, N 3, 479-485
  作者：HONG, PANGBU、MISE, TAKAYA、YAMAZAKI, HIROSHI

  DOI：——

  日期：——