1-chloro-2,3,3,4,4-pentafluorocyclobutene | 377-94-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 1-chloro-2,3,3,4,4-pentafluorocyclobutene
• 英文别名: 1-chloro-pentafluorocyclobutene；1-chloro-2,3,3,4,4-pentafluoro-cyclobutene；1-Chlor-2,3,3,4,4-pentafluor-cyclobuten；1-chloropentafluorocyclobutene；1-Chlor-pentafluorcyclobuten；1-Chloro-2,3,3,4,4-pentafluorocyclobut-1-ene
• CAS: 377-94-6
• 化学式: C₄ClF₅
• 分子量: 178.489
• InChiKey: OZTHTGSYTZIRML-UHFFFAOYSA-N

物化性质

• 沸点：
  33-38 °C
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-chloro-2,3,3,4,4-pentafluorocyclobutene 在 potassium fluoride 、 N-氯代丁二酰亚胺 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 4.5h， 以68%的产率得到1,1-dichloro-hexafluorocyclobutane
  参考文献：
  名称：

  JP5682381

  摘要：

  公开号：
• 作为产物：
  描述：

  1,1,2-trichloro-2,3,3,4,4-pentafluoro-cyclobutane 在 锌 、 正丁醇 作用下， 生成 1-chloro-2,3,3,4,4-pentafluorocyclobutene
  参考文献：
  名称：

  Reaction of Polyfluoro Olefins. VII.¹ Reactions of Pyridine and Derivatives with Hexafluorocyclobutene²

  摘要：

  DOI：

  10.1021/ja01127a007

文献信息

• METHOD FOR PRODUCING HYDROGEN-CONTAINING FLUOROOLEFIN COMPOUND
  申请人：Sugimoto Tatsuya

  公开号：US20110060170A1

  公开（公告）日：2011-03-10

  An unsaturated hydrogen-containing fluoroolefin compound is obtained by bringing an unsaturated fluorine-containing halogen compound into contact with 0.1 to 3 molar equivalents of hydrogen relative to the unsaturated fluorine-containing halogen compound in a vapor phase in the presence of a supported palladium catalyst in which an amount of supported palladium is 0.1% by weight to 2.5% by weight.

  通过将含不饱和氟的卤素化合物与相对于不饱和氟卤化合物在蒸汽相中的氢的摩尔当量为0.1到3的氢接触，在存在支撑的钯催化剂的情况下，获得含有不饱和氢的氟烯烃化合物，其中支撑的钯的含量为0.1%至2.5%的重量。
• 有机溶剂提供氢源发生氢-卤交换反应制备 1H-全卤环烯烃的方法
  申请人：北京宇极科技发展有限公司

  公开号：CN107365244B

  公开（公告）日：2020-05-15

  本发明涉及“有机溶剂提供氢源发生氢‑卤交换反应制备1H‑全卤环烯烃的方法”，属于化学合成领域。该方法在有溶剂的条件下，以1‑氯‑全卤环烯烃包括1,2‑二氯四氟环丁烯、1‑氯五氟环丁烯、1,2‑二氯六氟环戊烯、1‑氯七氟环戊烯、1‑氯九氟环己烯、1,2‑二氯八氟环戊烯等1‑氯‑全卤环烯烃为原料，与锌粉于反应温度为30～180℃，发生选择性氢‑卤交换反应而制得1H‑全卤环烯烃。本发明方法不仅反应条件温和、1H‑全卤环烯烃选择性高，而且是由N,N‑二甲基甲酰胺、N,N‑二甲基乙酰胺、N,N‑二乙基甲酰胺或N,N‑二乙基乙酰胺提供氢源发生氢化反应，工艺安全可靠，在工业上可通过普通的蒸馏手段进行有效分离。
• The preparation of partially fluorinated fused ring hydrocarbons
  作者：Donald J. Burton、Bernard A. Link

  DOI：10.1016/s0022-1139(00)81152-5

  日期：1983.4

  Diels-Alder reactions of fluorinated cyclobutenes and cyclopentenes with 1,3-butadiene and substituted 1,3-butadienes readily provide partially fluorinated fused ring systems. Hydrogenation, aromatization, acid hydrolysis and dehydrohalogenation of these adducts is easily accomplished and affords useful synthetic routes to partially fluorinated compounds.

  氟化环丁烯和环戊烯与1,3-丁二烯和取代的1,3-丁二烯的Diels-Alder反应易于提供部分氟化的稠环系统。这些加合物的氢化，芳构化，酸水解和脱卤化氢很容易完成，并为部分氟化的化合物提供了有用的合成途径。
• 卤代环烯烃水解制备氢卤环烯烃的方法
  申请人：北京宇极科技发展有限公司

  公开号：CN111423306A

  公开（公告）日：2020-07-17

  本发明涉及“卤代环烯烃水解制备氢卤环烯烃的方法”，属于化学合成领域。该方法在能与水混溶的非质子极性溶剂中，锌粉诱导式(I)的卤代环烯烃与水发生水解反应得到氢卤环烯烃式(II)和式(III)，反应温度为50～180℃。本发明方法不仅反应条件温和、氢卤环烯烃选择性高，而且后处理简便、环保，在工业上可通过普通的蒸馏手段进行有效分离。
• Structure-pulmonary toxicity/retention relationships of inhaled fluorocyclobutenes
  作者：M. P. Maidment、S. K. Patel、D. G. Upshall、C. M. Timperley

  DOI：10.1002/(sici)1099-1263(199903/04)19:2<113::aid-jat551>3.0.co;2-y

  日期：1999.3

  Hexafluorocyclobutene (HFCB) and derivatives have been used as fumigants, refrigerants and polymerization monomers, When inhaled they produce a potentially fatal pulmonary oedema similar to that induced by perfluoroisobutene (PFIB), a by-product of Teflon manufacture. This study determined the relationship between the chemical structure, respiratory retention and toxicity of HFCB and five analogues in rats and mice. Retention in the rat was determined using a flow-through system combining nose-only exposure and plethysmography, Structural changes to HFCB modified retention. At concentrations of ca, 1 ppm, where uptake was independent of exposure time, the rate of uptake was increased by halogen substitution in the order 3-Br = 1-Br = 1-Cl > 3-Cl = 1-H > HFCB, and was a function of volatility. At concentrations of 6 or 30 ppm, the percentage retained and rate of uptake decreased with time. The total mass retained (mu mol kg(-1)) was not proportional to inhaled concentration and was best described by the calculated partition coefficient (octane-water), No clear relationship between retention and reactivity was apparent. The contribution of volatility, partition coefficient and reactivity to the uptake process depended on inhaled concentration, The toxicity of the fluorocyclobutenes agreed with reactivity relationships based on electrophilicity (lowest unoccupied molecular orbital energy), carbanion stability and leaving-group mobility. Toxicity is based principally on the number of successive alkylations (1, 2 or 3) that can occur with tissue nucleophiles. Copyright (C) 1999 John Wiley & Sons, Ltd.