(Z)-10-Iodo-2-(1'-naphthylmethylidene)deca-3,9-diynal | 359400-23-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-10-Iodo-2-(1'-naphthylmethylidene)deca-3,9-diynal
• 英文别名: (2Z)-10-iodo-2-(naphthalen-1-ylmethylidene)deca-3,9-diynal
• CAS: 359400-23-0
• 化学式: C₂₁H₁₇IO
• 分子量: 412.27
• InChiKey: NCKFOSJBTNCCTQ-VLGSPTGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-10-Iodo-2-(1'-naphthylmethylidene)deca-3,9-diynal 在 chromium dichloride 、 nickel dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以30%的产率得到(E)-4-(1'-Naphthylmethylidene)cyclodeca-1,5-diyn-3-ol
  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：

  3-napthalen-1-yl-acrylic acid methyl ester 在 copper(l) iodide 、 四(三苯基膦)钯 吗啉 、 N-乙基哌啶 、 重铬酸吡啶 、 溴 、 碘 、 二异丁基氢化铝 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 1.0h， 生成 (Z)-10-Iodo-2-(1'-naphthylmethylidene)deca-3,9-diynal
  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

• Enediyne derivatives
  申请人：The Hong Kong University of Science and Technology

  公开号：US06391916B1

  公开（公告）日：2002-05-21

  Novel C3-substituted cyclodeca-1,5-diynes can be prepared through novel synthetic procedures using starting (E)-C3-substituted-4-(aryl- or heteroarylmethylidene)cyclodeca-1,5-diynes reagents. Both the C3-substituted cyclodeca-1,5-diyn-3-enes and the starting reagents have improved thermal stability compared to unsubstituted counterparts.

  可以通过新颖的合成方法，使用起始物(E)-C3-取代-4-(芳基或杂环芳基甲基)环十碳-1,5-二炔试剂，制备新颖的C3-取代环十碳-1,5-二炔。与未取代的对应物相比，这些C3-取代环十碳-1,5-二炔-3-烯和起始试剂都具有更好的热稳定性。
• US6391916B1
  申请人：——

  公开号：US6391916B1

  公开（公告）日：2002-05-21
• 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.