1-chloro-4-(difluoroiodomethylsulfanyl)benzene | 272788-39-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-chloro-4-(difluoroiodomethylsulfanyl)benzene
• 英文别名: 1-Chloro-4-[difluoro(iodo)methyl]sulfanylbenzene
• CAS: 272788-39-3
• 化学式: C₇H₄ClF₂IS
• 分子量: 320.529
• InChiKey: JGIVJMBZNUDNBW-UHFFFAOYSA-N

物化性质

• 沸点：
  217.5±40.0 °C(Predicted)
• 密度：
  1.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,3-二甲基-4-戊烯酸 、 1-chloro-4-(difluoroiodomethylsulfanyl)benzene 在 sodium hydroxide 、 sodium dithionite 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 以64.2%的产率得到5-[2-(4-chlorophenylsulfanyl)-2,2-difluoro-ethyl]-4,4-dimethyl-dihydro-furan-2-one
  参考文献：
  名称：

  二氟碘甲基硫烷基苯的新制备及其由连二亚硫酸钠引发的不饱和化合物的自由基加成

  摘要：

  二氟碘甲基硫烷基苯（3a）和1-氯-4-二氟碘甲基硫烷基苯（3b）是通过与不饱和化合物（如烯烃，乙炔基苯，戊-4-烯-1-醇和戊-4-烯醇）反应而形成的新型高效二氟甲基化试剂。由Na 2 S 2 O 4引发的酸，以中等至良好的产率得到相应的加合物，四氢呋喃衍生物和含二氟亚甲基的γ-丁内酯。

  DOI：

  10.1016/j.tet.2007.12.018
• 作为产物：
  描述：

  (p-chlorophenylsulfinyl)difluoroacetic acid 在 五氯化磷 、 mercury(II) oxide 、 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.5h， 生成 1-chloro-4-(difluoroiodomethylsulfanyl)benzene
  参考文献：
  名称：

  Aryliododifluoromethylsulfides, sulfoxides and sulfones: the first optically active compounds with polyfluoroalkyliodo groups

  摘要：

  Aryliododifluoromethyl sulfoxides, which were transformed in aryliododifluoromethyl sulfides and sulfones, were obtained by the coupling of mercury salts of arylsulfoxydifluoromethylacetic acids with iodine.

  DOI：

  10.1070/mc2006v016n03abeh002314

文献信息

• One-Pot Addition-Intramolecular N-Cyclization of Carbamates Mediated by Alkali Metallic Reagents as an Approach to 4-(Fluoroalkyl)oxazolidin-2-ones
  作者：Xiang Fang、Fan-Hong Wu、Xue-Yan Yang、Zheng-Hua Ju、Yun-Li Hu

  DOI：10.1055/s-0030-1260239

  日期：2011.11

  straightforward strategy for the synthesis of 4-(fluoroalkyl)oxazolidin-2-ones via one-pot addition-intramolecular N-cyclization of allyl carbamates with fluoroalkyl iodides is presented. The reaction proceeded in moderate to good yield through regiocontrol and an increase in the reactivity of the ambident nucleophiles by the use of alkali metallic reagents. allyl carbamates - 4-(fluoroalkyl)oxazolidin-2-ones -

  提出了一种温和简单的策略，通过一锅加成-分子内烯丙基氨基甲酸酯与氟代烷基碘的N-环化反应，合成4-（氟代烷基）恶唑烷-2-酮。通过区域控制和使用碱金属试剂增加环境亲核试剂的反应性，反应以中等至良好的产率进行。 氨基甲酸烯丙酯-4-（氟烷基）恶唑烷-2-酮-加成-分子内N-环化-碱金属试剂
• Sodium Dithionite Initiated Addition-lactonization of 2-Acyl- amino-4-pentenoic Acids with Fluoroalkyl Iodides to Synthesize 4-Fluoroalkyl-2-acylamino-4-butyrolactones
  作者：Xueyan Yang、Xianjin Yang、Shengjie Zhu、Lingling Ye、Yang Chen、Guanlong Chen、Fanhong Wu

  DOI：10.1002/cjoc.201090375

  日期：2010.11

  4‐Fluoroalkyl‐2‐acylamino‐4‐butyrolactones were afforded in moderate yields by the sodium dithionite initiated one‐pot addition‐lactonization reaction of polyfluoroalkyl iodides with 2‐acylamino‐4‐pentenoic acids.

  亚硫酸氢钠引发的多氟烷基碘与2-酰基氨基-4-戊烯酸的一锅加成-内酯化反应提供了中等收率的4-氟烷基-2-酰基氨基-4-丁内酯。
• AIBN-initiated radical addition of gem-difluorinated alkyl iodides to alkynes and the Pd-catalyzed Sonogashira coupling reaction of E-phenyl difluoromethylene vinylic iodides with terminal alkynes
  作者：Xiang Fang、Xueyan Yang、Xianjin Yang、Shenjie Mao、Zhonghua Wang、Guorong Chen、Fanhong Wu

  DOI：10.1016/j.tet.2007.07.087

  日期：2007.10

  The addition of gem-difluorinated alkyl iodides to alkynes initiated by AIBN neatly gave the corresponding difluoromethylene vinyl iodides among which the stereoselectivity of aromatic acetylenes was high. The further coupling reaction of E-phenyl difluoromethylene vinyl iodides with terminal alkynes in the presence of catalytic palladium afforded the substituted difluorinated enynes.

  加入宝石-difluorinated烷基碘于由AIBN引发炔整齐，得到相应的二氟亚甲基乙烯基碘化物其中芳族乙炔的立体选择性是很高的。在催化钯的存在下，E-苯基二氟亚甲基乙烯基碘与末端炔的进一步偶联反应得到取代的二氟烯。
• A Convergent Route to Geminal Difluorosulfides and to Functionalized Difluorothiochromans, a New Family of Organofluorine Compounds
  作者：Pierre Salomon、Samir Z. Zard

  DOI：10.1021/ol5002939

  日期：2014.3.7

  The synthesis of the novel O-ethyl-S-(4-chlorophenylthio)difluoromethyl xanthate and its radical addition to various terminal alkenes are described. The geminal difluorosulfide adducts undergo closure onto the aromatic ring by further treatment with peroxide to furnish difluorothiochromans, a new family of organofluorine compounds.
• The reactions of difluorodiiodomethane with nucleophiles
  作者：Yong Guo、Qing-Yun Chen

  DOI：10.1016/s0022-1139(99)00228-6

  日期：2000.3

  Treatment of difluorodiiodomethane with phenoxides (ArO-) in DMF at room temperature gives ArOCF2I in 7-15%, the carbonates (ArOCO2Ar) being the major products, while with thiophenoxides affords difluoromethylene derivatives (ArSCF2I, ArSCF2SAr, and ArSCF2H) also in low yields. (C) 2000 Elsevier Science S.A. All rights reserved.