1-(3,3-difluoroprop-1-yn-1-yl)-4-methoxybenzene | 1150634-74-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(3,3-difluoroprop-1-yn-1-yl)-4-methoxybenzene
• 英文别名: 1-(3,3-difluoroprop-1-ynyl)-4-methoxybenzene；1-(3,3-Difluoro-1-propynyl)-4-methoxybenzene
• CAS: 1150634-74-4
• 化学式: C₁₀H₈F₂O
• 分子量: 182.17
• InChiKey: OGNCCXVTRSJYMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3,3-difluoroprop-1-yn-1-yl)-4-methoxybenzene 以 甲苯 为溶剂， 反应 4.5h， 生成 1-difluoromethyl-2-(4-methoxyphenyl)-3,4,5,6-tetraphenylbenzene
  参考文献：
  名称：

  Selective synthesis of fluoroalkyl-containing multisubstituted benzenes through Co-mediated [2+2+2] cycloaddition reaction with fluoroalkylated alkynes

  摘要：

  The reaction of various fluoroalkylated alkynes with 1.2 equiv of Co-2(CO)(8) in toluene at room temperature for 30 mm took place smoothly to give the corresponding alkyne-cobalt complex quantitatively. Without its purification, treatment of the in situ-generated complex with 6.0 equiv of various nonfluorinated alkynes at 130 degrees C for 4 h provided monofluoroallcylated multisubstituted benzenes in moderate to good yields. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2015.06.013
• 作为产物：
  描述：

  4-乙炔基苯甲醚 在 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 silver nitrate 作用下， 以 二甲基亚砜 、 丙酮 为溶剂， 反应 12.17h， 生成 1-(3,3-difluoroprop-1-yn-1-yl)-4-methoxybenzene
  参考文献：
  名称：

  Oxidant- and Base-Free, Copper-Catalyzed Difluoromethylation of Haloalkynes

  摘要：

  DOI：

  10.1021/acs.orglett.3c03198

文献信息

• Difluoromethylation of Terminal Alkynes by Fluoroform
  作者：Satoshi Okusu、Etsuko Tokunaga、Norio Shibata

  DOI：10.1021/acs.orglett.5b01778

  日期：2015.8.7

  The difluoromethylation of terminal alkynes through the use of fluoroform as a source of difluorocarbene is described. The choice of solvents and bases was found to be crucial for the transformation. A series of terminal alkynes 1 were nicely converted into the corresponding difluoromethyl alkynes 2 using potassium tert-butoxide in n-decane in moderate to good yields. Functional groups such as methoxy

  描述了通过使用氟仿作为二氟卡宾的来源而使末端炔烃的二氟甲基化。发现溶剂和碱的选择对于转化至关重要。使用叔丁醇钾在正癸烷中的适当收率，将一系列末端炔烃1很好地转化为相应的二氟甲基炔烃2。在反应条件下，对甲氧基，二甲氨基和溴等官能团以及苯基，杂芳基和空间要求的萘基具有很好的耐受性。二氟甲基炔烃2一步转化为二氟甲基化的异恶唑3和1,2,3-三唑4 也实现了。
• A novel synthesis of fluorine-containing cyclopentenones via Pauson–Khand reaction
  作者：Tsutomu Konno、Takumi Kida、Akinori Tani、Takashi Ishihara

  DOI：10.1016/j.jfluchem.2012.08.006

  日期：2012.12

  Intermolecular Pauson–Khand reaction of fluoroalkylated alkynes with 2-norbornene or 2,5-norbornadiene at the reflux temperature of dichloroethane proceeded smoothly to give the corresponding cyclopentenone derivatives in high yields as a mixture of regioisomers. On the other hand, intramolecular Pauson–Khand reaction of fluorine-containing 1,6-enyne proceeded in the presence of NMO or TMANO to give

  在二氯乙烷回流温度下，氟烷基化炔烃与2-降冰片烯或2,5-降冰片二烯的分子间Pauson-Khand反应顺利进行，从而以区域异构体的混合物形式高收率地得到了相应的环戊烯酮衍生物。另一方面，在NMO或TMANO的存在下，含氟1,6-烯炔的分子内Pauson-Khand反应进行，从而以高收率得到双环加合物。另外，烯丙基CF 3-炔丙基醚在氧化胺存在下也进行了平稳的Pauson-Khand反应，相应的双环化合物以非对映选择性的方式获得。
• [Ph ₄ P] ⁺ [Cu(CF ₂ H) ₂ ] ⁻ : A Powerful Difluoromethylating Reagent Inspired by Mechanistic Investigation
  作者：Haiwei Zhao、Xuebing B. Leng、Wei Zhang、Qilong Shen

  DOI：10.1002/anie.202210151

  日期：2022.10.17

  A powerful difluoromethylating reagent [Ph4P]+[Cu(CF2H)2]− that was able to difluoromethylate a variety of aryl and alkyl electrophiles was developed. In the presence of an oxidant, complex 2 also reacted with various lithium nbutyl arylboronic acid pinacol esters, alkyne and heteroarene. Moreover, complex 2 could transmetalate the difluoromethyl reagent to other metals such as [Ph4P]+[Cu(Cl2)]− and

  开发了一种强大的二氟甲基化试剂 [Ph 4 P] + [Cu(CF 2 H) 2 ] −，它能够二氟甲基化各种芳基和烷基亲电子试剂。在氧化剂存在下，络合物2还与各种锂正丁基芳基硼酸频哪醇酯、炔烃和杂芳烃反应。此外，络合物2可以将二氟甲基试剂金属转移到其他金属，例如 [Ph 4 P] + [Cu(Cl 2 )] -和 [(DPPF)Pd(Cl) 2 ]。
• Copper-Catalyzed Synthesis of Difluoromethyl Alkynes from Terminal and Silyl Acetylenes
  作者：Xanath Ispizua-Rodriguez、Vinayak Krishnamurti、Vanessa Carpio、Colby Barrett、G.K. Surya Prakash

  DOI：10.1021/acs.joc.2c02799

  日期：2023.1.20

  An efficient method for the direct C(sp)–H difluoromethylation of terminal alkynes and the desilylation–difluoromethylation of (trimethylsilyl)acetylenes is disclosed. The copper-catalyzed transformation provides access to a wide range of structurally diverse CF2H alkynes in good yields, utilizing a (difluoromethyl)zinc reagent and an organic oxidant. The difluoromethylation of important synthons and

  公开了一种用于末端炔烃的直接 C(sp)-H 二氟甲基化和（三甲基甲硅烷基）乙炔的脱甲硅烷基化-二氟甲基化的有效方法。利用（二氟甲基）锌试剂和有机氧化剂，铜催化的转化以良好的产率提供了广泛的结构多样的 CF 2 H 炔烃。展示了重要合成子和 API 的二氟甲基化。这些 (二氟甲基) 炔烃的合成效用通过选定的环加成反应得到证明。此外，对反应条件的轻微修改允许选择性制备 2-二氟甲基吲哚。
• <i>N</i>-Tosyl-<i>S</i>-difluoromethyl-<i>S</i>-phenylsulfoximine: A New Difluoromethylation Reagent for S-, N-, and C-Nucleophiles
  作者：Wei Zhang、Fei Wang、Jinbo Hu

  DOI：10.1021/ol900567c

  日期：2009.5.21

  The first alpha-difluoromethyl sulfoximine compound, 2, was successfully prepared by using the copper(II)-catalyzed nitrene transfer reaction. Compound 2 was found to be a novel and efficient difluoromethylation reagent for transferring the CF2H group to S-, N-, and C-nucleophiles. Deuterium-labeling experiments suggest that a difluorocarbene mechanism is involved in the current difluoromethylation reactions.