3-(2,3,4,5,6-五氟苯基)丙-2-炔酸 | 61794-54-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(2,3,4,5,6-五氟苯基)丙-2-炔酸
• 英文名称: 3-pentafluorophenyl-2-propynoic acid
• 英文别名: 3-(Pentafluorophenyl)prop-2-ynoic acid；3-(2,3,4,5,6-pentafluorophenyl)prop-2-ynoic acid
• CAS: 61794-54-5
• 化学式: C₉HF₅O₂
• 分子量: 236.098
• InChiKey: JQMWIIYFMQIPHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,3,4,5,6-五氟碘苯 生成 3-(2,3,4,5,6-五氟苯基)丙-2-炔酸
  参考文献：
  名称：

  聚氟苯基乙炔及相关化合物

  摘要：

  由五氟和4-取代的四氟碘苯（取代基R为CF 3-，H-，CH 3-或CH 3 O-）与铜（I）3-（2'-四氢吡喃氧基）丙-1的反应已获得相应的3-（聚氟苯基）丙-2-炔醇衍生物。其中R = N（CH 3）2-和NH 2-未获得炔属醇；这些是通过二甲胺和氨与3-（五氟苯基）丙-2-炔醇本身的反应合成的。通过在二恶烷/ NaOH水溶液中的过氧化镍将炔醇转化为相应的多氟苯基乙炔。用60℃的苯作为溶剂，将3-（五氟苯基）丙-2-炔醇氧化成醛和酸，在回流的苯中，得到1-4双（多氟苯基）丁二炔和多氟苯基乙炔。已经讨论了一些反应的机理。

  DOI：

  10.1016/0040-4020(76)85181-2

文献信息

• Thieme Chemistry Journal Awardees - Where Are They Now? Pentafluorophenyl End-Capped Polyynes as Supramolecular Building Blocks
  作者：Rik Tykwinski、Jamie Kendall、Robert McDonald

  DOI：10.1055/s-0029-1217706

  日期：2009.8

  The synthesis of pentafluorophenyl end-capped polyynes up to an octayne has been developed based on the use of a Fritsch-Buttenberg-Wiechell rearrangement as the key step. UV/ Vis spectroscopic analysis shows little change in the electronic nature of these structures as phenyl is formally replaced by pentafluorophenyl. The ability of pentafluorophenyl polyynes to function as supramolecular building

  基于使用 Fritsch-Buttenberg-Wiechell 重排作为关键步骤，开发了五氟苯基封端的聚炔合成至辛炔。紫外/可见光谱分析显示这些结构的电子性质几乎没有变化，因为苯基在形式上被五氟苯基取代。五氟苯基聚炔在主客体系统中作为超分子结构单元的能力通过在三炔 5 和十氟甲苯胺之间形成包合物来证明。
• METHOD FOR SYNTHESIS OF CIGUATOXIN CTX1B AND COMPOUND USEFUL FOR THE SYNTHESIS OF CIGUATOXIN CTX1B
  申请人：Japan Science and Technology Agency

  公开号：EP1982988A1

  公开（公告）日：2008-10-22

  Disclosed is a method for total synthesis of CTX1B, which is developed for the synthesis of a ciguatoxin analogue such as CTX3C and enables the more efficient application of an established reaction to the total synthesis of CTC1B. More specifically, disclosed is a method for total synthesis of CTX1B comprising; an O.S-acetal formation for synthesizing a novel compound (3); a radical cyclization reaction for constructing a 9-membered ring formation reaction including a novel compound (6) through a novel compound (8) and yielding a compound (D); and a deprotection for yielding CTX1B. Also disclosed are novel compounds (1) to (8) which are particularly useful for synthesis of CTX1B and can be used for the synthesis of a ciguatoxin analogue.

  本发明公开了一种 CTX1B 的全合成方法，该方法是为合成雪卡毒素类似物（如 CTX3C）而开发的，能够更有效地将已有反应应用于 CTC1B 的全合成。更具体地说，本发明公开了一种用于全合成 CTX1B 的方法，该方法包括：用于合成新型化合物 (3) 的 O.S-缩醛形成反应；用于构建包括新型化合物 (6) 通过新型化合物 (8) 的 9 元环形成反应并生成化合物 (D) 的自由基环化反应；以及用于生成 CTX1B 的脱保护反应。还公开了新型化合物（1）至（8），它们特别适用于合成 CTX1B，并可用于合成雪卡毒素类似物。
• METHOD OF SYNTHESIS OF CIGUATOXIN CTX1B AND COMPOUNDS USEFUL FOR THE SYNTHESIS OF CIGUATOXIN CTX1B
  申请人：Japan Science and Technology Agency

  公开号：EP1982988B1

  公开（公告）日：2014-06-04
• METHOD FOR SYNTHESIS OF CIGUATOXIN CTX1B AND COMPOUNDS USEFUL FOR THE SYNTHESIS OF CIGUATOXIN CTX1B
  申请人：Hirama Masahiro

  公开号：US20100160651A1

  公开（公告）日：2010-06-24

  Disclosed is a method for total synthesis of CTX1B, which is developed for the synthesis of a ciguatoxin analogue such as CTX3C and enables the more efficient application of an established reaction to the total synthesis of CTC1B. More specifically, disclosed is a method for total synthesis of CTX1B comprising; an 0.5-acetal formation for synthesizing a novel compound (3); a radical cyclization reaction for constructing a 9-membered ring formation reaction including a novel compound (6) through a novel compound (8) and yielding a compound (D); and a deprotection for yielding CTX1B. Also disclosed are novel compounds (1) to (8) which are particularly useful for synthesis of CTX1B and can be used for the synthesis of a ciguatoxin analogue.
• US7939679B2
  申请人：——

  公开号：US7939679B2

  公开（公告）日：2011-05-10