(Z)-2-fluoro-3-(thiophen-2-yl)allyl acetate | 1551191-15-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (Z)-2-fluoro-3-(thiophen-2-yl)allyl acetate
• 英文别名: [(Z)-2-fluoro-3-thiophen-2-ylprop-2-enyl] acetate
• CAS: 1551191-15-1
• 化学式: C₉H₉FO₂S
• 分子量: 200.234
• InChiKey: GOEOMMCGMXIDKN-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲基丙二酸二甲酯 、 (Z)-2-fluoro-3-(thiophen-2-yl)allyl acetate 在 2,2'-联吡啶 、 [Pd(C₃H₅)(cod)]BF₄ 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 12.0h， 以74%的产率得到(E)-tetramethyl 3-(thiophen-2-ylmethylene)hexane-2,2,5,5-tetracarboxylate
  参考文献：
  名称：

  Palladium-Catalyzed Double Alkylation of 3-Aryl-2-fluoroallyl Esters with Malonate Nucleophiles through the Carbon–Fluorine Bond Cleavage

  摘要：

  The alkylation of (Z)-3-aryl-2-fluoroallyl acetate with the malonate anion by the [Pd(C3H5)(cod)]BF4/2,2'-bpy catalyst proceeds through the carbon fluorine bond cleavage, and 2 equiv of the malonate nucleophile was introduced to the allyl substrate.

  DOI：

  10.1021/ol500121z

文献信息

• Palladium-catalyzed intermolecular coupling of 2-haloallylic acetates with simple phenols, and sequential formation of benzofuran derivatives through the intramolecular cyclization
  作者：Takumi Udagawa、Yukiko Tsuchi、Ikuma Takehara、Masaki Kogawa、Hirotaka Watanabe、Mitsuaki Yamamoto、Hiroaki Tsuji、Motoi Kawatsura

  DOI：10.1016/j.tet.2017.10.001

  日期：2017.11

  synthesis of 2-substituted benzofuran derivatives by the palladium-catalyzed reaction of 2-haloallylic acetates with simple phenols in the presence of a base. The reaction proceeded through the intermolecular attack of the nucleophile on the central carbon atom of the π-allyl group, carbon-halogen bond cleavage, and sequential intramolecular cyclization.

  我们在碱的存在下，通过2-卤代烯丙基乙酸盐与简单酚的钯催化反应，完成了2-取代的苯并呋喃衍生物的合成。该反应通过亲核体对π-烯丙基的中心碳原子的分子间攻击，碳-卤素键的裂解以及依次的分子内环化而进行。
• Palladium-Catalyzed Regioselective Hydroalkylation of 2-Fluoroallyl Acetates: Synthesis of Vinylmalonic Acid Ester Derivatives
  作者：Motoi Kawatsura、Shihori Kuki、Takashi Futamura、Ryo Suzuki、Mitsuaki Yamamoto、Maki Minakawa

  DOI：10.1055/s-0034-1380747

  日期：——

  The palladium-catalyzed hydroalkylation of 2-fluoroallyl acetates with the malonate anion and hydride was developed. The reaction proceeded through the C–F bond activation and provided vinylmalonic acid ester derivatives by the regioselective substitutions with the carbon nucleophile and hydride.

  开发了钯催化的乙酸烯丙酯与丙二酸阴离子和氢化物的加氢烷基化反应。该反应通过 C-F 键活化进行，并通过与碳亲核试剂和氢化物的区域选择性取代提供乙烯基丙二酸酯衍生物。
• Palladium-Catalyzed Double Substitution of 3-Aryl-2-fluoroallyl Acetates with Phenols via C–F Bond Activation
  作者：Motoi Kawatsura、Eito Nomada、Hirotaka Watanabe、Mitsuaki Yamamoto、Takumi Udagawa、Biao Zhou、Akiko Kobayashi、Maki Minakawa

  DOI：10.1055/s-0033-1339106

  日期：——

  The double substitution of 3-aryl-2-fluoroallyl acetates with phenols has been accomplished; the Pd(PPh3)(4) catalyst system has effectively catalyzed the reaction to afford the doubly substituted product via carbon-fluorine bond activation.