Methyl 2-(naphthalen-2-ylmethylidene)deca-3,9-diynoate | 359400-13-8

• 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 2-(naphthalen-2-ylmethylidene)deca-3,9-diynoate
• 英文别名: methyl 2-(naphthalen-2-ylmethylidene)deca-3,9-diynoate
• CAS: 359400-13-8
• 化学式: C₂₂H₂₀O₂
• 分子量: 316.4
• InChiKey: DLTRQFBMCDJIDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  Methyl 2-(naphthalen-2-ylmethylidene)deca-3,9-diynoate 在 吗啉 、 chromium dichloride 、 碘 、 二异丁基氢化铝 、 pyridinium chlorochromate 、 nickel dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 9.0h， 生成 10-[1-Naphthalen-2-yl-meth-(E)-ylidene]-cyclodeca-2,8-diynol
  参考文献：
  名称：

  Intramolecular Nozaki–Hiyama–Kishi reactions and Ln(III)-catalyzed allylic rearrangement as the key steps towards 10-membered ring enediynes

  摘要：

  A general and facile synthesis of the 3-substituted 10-membered ring enediynes 18-22 from the aldehydes 8 and 15 has been established by utilizing the intramolecular Nozaki-Hiyama-Kishi reaction and the lwanthanide(III)-catalyzed rearrangement of allylic alkoxyacetates as the key steps. This work provides ready access to the (E)-3-acyloxy-4-(arylmethylidene)cyclodeca-1,5-diynes, which can be converted into the bioactive enediynes under physiological conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00707-9
• 作为产物：
  描述：

  methyl (E)-3-(naphthalen-2-yl)acrylate 在 copper(l) iodide 、 四(三苯基膦)钯 N-乙基哌啶 、 溴 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 Methyl 2-(naphthalen-2-ylmethylidene)deca-3,9-diynoate
  参考文献：
  名称：

  Intramolecular Nozaki–Hiyama–Kishi reactions and Ln(III)-catalyzed allylic rearrangement as the key steps towards 10-membered ring enediynes

  摘要：

  A general and facile synthesis of the 3-substituted 10-membered ring enediynes 18-22 from the aldehydes 8 and 15 has been established by utilizing the intramolecular Nozaki-Hiyama-Kishi reaction and the lwanthanide(III)-catalyzed rearrangement of allylic alkoxyacetates as the key steps. This work provides ready access to the (E)-3-acyloxy-4-(arylmethylidene)cyclodeca-1,5-diynes, which can be converted into the bioactive enediynes under physiological conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00707-9

文献信息

• Intramolecular Nozaki–Hiyama–Kishi reactions and Ln(III)-catalyzed allylic rearrangement as the key steps towards 10-membered ring enediynes
  作者：Wei-Min Dai、Anxin Wu、Wataru Hamaguchi

  DOI：10.1016/s0040-4039(01)00707-9

  日期：2001.6

  A general and facile synthesis of the 3-substituted 10-membered ring enediynes 18-22 from the aldehydes 8 and 15 has been established by utilizing the intramolecular Nozaki-Hiyama-Kishi reaction and the lwanthanide(III)-catalyzed rearrangement of allylic alkoxyacetates as the key steps. This work provides ready access to the (E)-3-acyloxy-4-(arylmethylidene)cyclodeca-1,5-diynes, which can be converted into the bioactive enediynes under physiological conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.