methyl 2-fluoro-6-(3-hydroxyprop-1-ynyl)benzoate | 272130-52-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-fluoro-6-(3-hydroxyprop-1-ynyl)benzoate
• 英文别名: methyl 2-fluoro-6-(3-hydroxyprop-1-yn-1-yl)benzoate
• CAS: 272130-52-6
• 化学式: C₁₁H₉FO₃
• 分子量: 208.189
• InChiKey: PIVSEXPBKKZGDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-fluoro-6-(3-hydroxyprop-1-ynyl)benzoate 在 palladium on activated charcoal sodium tetrahydroborate 、 四溴化碳 、 氢气 、 sodium hydride 、 三苯基膦 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 methyl 2-fluoro-6-[3-(8-hydroxy-7,8-dihydro-4H-imidazo[4,5-d][1,3]diazepin-3-yl)propyl]benzoate
  参考文献：
  名称：

  AMP Deaminase Inhibitors. 3. SAR of 3-(Carboxyarylalkyl)coformycin Aglycon Analogues

  摘要：

  N3-Substituted coformycin aglycon analogues with improved AMP deaminase (AMPDA) inhibitory potency are described. Replacement of the 5-carboxypentyl substituent in the lead AMPDA inhibitor 3-(5-carboxypentyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (2) described in the previous article with various carboxyarylalkyl groups resulted in compounds with 10-100-fold improved AMPDA inhibitory potencies. The optimal N3 substituent had m-carboxyphenyl with a two-carbon alkyl tether. For example, 3-[2-(3-carboxy-5-ethylphenyl)-ethyl]-3,6,7,8-tetrahydroimidazo[4,5-d] [1,3]diazepin-8-ol (43g) inhibited human AMPDA with a K-i = 0.06 mu M. The compounds within the series also exhibited >1000-fold specificity for AMPDA relative to adenosine deaminase.

  DOI：

  10.1021/jm990448e
• 作为产物：
  描述：

  2-丙炔-1-醇 、 2-氟-6-碘苯甲酸甲酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到methyl 2-fluoro-6-(3-hydroxyprop-1-ynyl)benzoate
  参考文献：
  名称：

  烯丙醇的催化脱水酸化

  摘要：

  报道了合成邻苯二甲酸盐和γ-丁内酯的简便策略。该方法在正式的Au（I）和Pd（II）催化的S N 2'反应中利用易于制备的烯丙醇。使用这些催化剂，观察到所需五元内酯的排他形成，完全避免了竞争的直接内酯化途径，后者与质子酸和其他金属盐形成了不希望的七元环。这种温和且操作简单的方法尤其可以耐受环乙亚甲基，应在邻苯二甲酸酯和萜烯合成中找到用途。

  DOI：

  10.1021/acs.orglett.8b01063

文献信息

• Catalytic Dehydrative Lactonization of Allylic Alcohols
  作者：Ji Liu、Romain J. Miotto、Julien Segard、Ashley M. Erb、Aaron Aponick

  DOI：10.1021/acs.orglett.8b01063

  日期：2018.5.18

  the synthesis of phthalides and γ-butyrolactones is reported. The method utilizes readily prepared allylic alcohols in formal Au(I)- and Pd(II)-catalyzed SN2′ reactions. Using these catalysts, exclusive formation of the desired five-membered lactones is observed, completely avoiding the competing direct lactonization pathway that forms the undesired seven-membered ring with protic acids and alternative

  报道了合成邻苯二甲酸盐和γ-丁内酯的简便策略。该方法在正式的Au（I）和Pd（II）催化的S N 2'反应中利用易于制备的烯丙醇。使用这些催化剂，观察到所需五元内酯的排他形成，完全避免了竞争的直接内酯化途径，后者与质子酸和其他金属盐形成了不希望的七元环。这种温和且操作简单的方法尤其可以耐受环乙亚甲基，应在邻苯二甲酸酯和萜烯合成中找到用途。
• AMP Deaminase Inhibitors. 3. SAR of 3-(Carboxyarylalkyl)coformycin Aglycon Analogues
  作者：Srinivas Rao Kasibhatla、Brett C. Bookser、Gary Probst、James R. Appleman、Mark D. Erion

  DOI：10.1021/jm990448e

  日期：2000.4.1

  N3-Substituted coformycin aglycon analogues with improved AMP deaminase (AMPDA) inhibitory potency are described. Replacement of the 5-carboxypentyl substituent in the lead AMPDA inhibitor 3-(5-carboxypentyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (2) described in the previous article with various carboxyarylalkyl groups resulted in compounds with 10-100-fold improved AMPDA inhibitory potencies. The optimal N3 substituent had m-carboxyphenyl with a two-carbon alkyl tether. For example, 3-[2-(3-carboxy-5-ethylphenyl)-ethyl]-3,6,7,8-tetrahydroimidazo[4,5-d] [1,3]diazepin-8-ol (43g) inhibited human AMPDA with a K-i = 0.06 mu M. The compounds within the series also exhibited >1000-fold specificity for AMPDA relative to adenosine deaminase.
• Enantioselective Lactonization by π‐Acid‐Catalyzed Allylic Substitution: A Complement to π‐Allylmetal Chemistry
  作者：Arun Raj Kizhakkayil Mangadan、Ji Liu、Aaron Aponick

  DOI：10.1002/anie.202108336

  日期：2021.10.4

  Asymmetric allylic alkylation (AAA) is a powerful method for the formation of highly useful, non-racemic allylic compounds. Here we present a complementary enantioselective process that generates allylic lactones via π-acid catalysis. More specifically, a catalytic enantioselective dehydrative lactonization of allylic alcohols using a novel PdII-catalyst containing the imidazole-based P,N-ligand (S)-StackPhos

  不对称烯丙基烷基化 (AAA) 是形成非常有用的非外消旋烯丙基化合物的有效方法。在这里，我们提出了一种互补的对映选择性过程，该过程通过 π 酸催化生成烯丙内酯。更具体地说，报道了使用含有咪唑基P , N-配体 ( S )-StackPhos的新型 Pd II催化剂对烯丙醇进行催化对映选择性脱水内酯化。高产率反应操作简单，对映选择性高达 99 % ee. 该策略有助于用表面上更好的离去基团替换产品中的不良离去基团，避免因平衡外消旋化而引起的并发症。