naphthalen-2-yl but-3-enoate | 93359-81-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphthalen-2-yl but-3-enoate
• CAS: 93359-81-0
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: SLTPGZMCEOBIAT-UHFFFAOYSA-N

物化性质

• 沸点：
  350.7±21.0 °C(Predicted)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  naphthalen-2-yl but-3-enoate 在 sodium sulfate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以86%的产率得到naphthalen-2-yl 2-(oxiran-2-yl)acetate
  参考文献：
  名称：

  Enantioselective Radiosynthesis of Positron Emission Tomography (PET) Tracers Containing [¹⁸F]Fluorohydrins

  摘要：

  Herein, we describe an operationally straightforward radiosynthesis of a chiral transition metal fluoride catalyst, [F-18](salen)CoF, and its use for late-stage enantioselective aliphatic radiofluorination. We demonstrate the utility of the method by preparing single enantiomer experimental and clinically validated PET tracers that contain base-sensitive functional groups, epimerizable stereocenters, and nitrogen-rich motifs. Unlike the conventional radiosyntheses of these targets with [F-18]KF, labeling with (salen)CoF is possible in the last step and under exceptionally mild conditions. These results constitute a rare example of a nucleophilic radiofluorination using a transition metal fluoride and highlight the potential of such reagents to enhance traditional methods for labeling aliphatic hydrocarbons.

  DOI：

  10.1021/ja5025645
• 作为产物：
  描述：

  丁-3-烯酰氯 、 2-萘酚 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 24.5h， 以46%的产率得到naphthalen-2-yl but-3-enoate
  参考文献：
  名称：

  Enantioselective Radiosynthesis of Positron Emission Tomography (PET) Tracers Containing [¹⁸F]Fluorohydrins

  摘要：

  Herein, we describe an operationally straightforward radiosynthesis of a chiral transition metal fluoride catalyst, [F-18](salen)CoF, and its use for late-stage enantioselective aliphatic radiofluorination. We demonstrate the utility of the method by preparing single enantiomer experimental and clinically validated PET tracers that contain base-sensitive functional groups, epimerizable stereocenters, and nitrogen-rich motifs. Unlike the conventional radiosyntheses of these targets with [F-18]KF, labeling with (salen)CoF is possible in the last step and under exceptionally mild conditions. These results constitute a rare example of a nucleophilic radiofluorination using a transition metal fluoride and highlight the potential of such reagents to enhance traditional methods for labeling aliphatic hydrocarbons.

  DOI：

  10.1021/ja5025645

文献信息

• Photochemical reactions of naphthyl-vinyl non-conjugated bichromophoric systems
  作者：Annoula Kashoulis、Andrew Gilbert、Graham Ellis-Davies

  DOI：10.1016/s0040-4039(01)81322-8

  日期：1984.1

  2-(1-naphthyl)ethyl vinyl ether undergoes intramolecular 1,2- photocycloaddition whereas the 2-naphthyl isomer yields a product reflecting dimerisation and loss of the elements of acetylene: consistent with such diverse photochemistry, the addition of 2,3-dihydropyran to naphthalene produces only the 1,2-, 1′,2′regioisomer.

  2-（1-萘基）乙基乙烯基醚经历分子内1,2-光环加成，而2-萘基异构体产生的产物反映二聚化和乙炔元素的损失：与这种多样的光化学相一致，添加了2,3-二氢吡喃萘仅产生1，2-，1'，2'区域异构体。
• KASHOULIS, A;GILBERT, A.;ELLIS-DAVIES, G., TETRAHEDRON LETT., 1984, 25, N 27, 2905-2908
  作者：KASHOULIS, A、GILBERT, A.、ELLIS-DAVIES, G.

  DOI：——

  日期：——