4-(4-(trifluoromethoxy)phenyl)-4-pentenoic acid | 1254701-52-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-(trifluoromethoxy)phenyl)-4-pentenoic acid
• 英文别名: 4-[4-(Trifluoromethoxy)phenyl]pent-4-enoic acid
• CAS: 1254701-52-4
• 化学式: C₁₂H₁₁F₃O₃
• 分子量: 260.213
• InChiKey: SQDYFLKASVSGPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(4-(trifluoromethoxy)phenyl)-4-pentenoic acid 在 N-溴代丁二酰亚胺(NBS) 、 O-[(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethyl] N-(2,4-dimethoxyphenyl)carbamothioate 、 4-硝基苯磺酰胺 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 24.0h， 以85%的产率得到5-(bromomethyl)-5-(4-trifluoromethoxyphenyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Asymmetric Bromolactonization Using Amino-thiocarbamate Catalyst

  摘要：

  A novel amino-thiocarbamate-catalyzed bromolactonization of unsaturated carboxylic acids has been developed. The scope of the reaction is evidenced by 22 examples of gamma-lactones with up to 99% yield and 93% ee. The protocol was applied in the enantioselective synthesis of the key intermediates of VLA-4 antagonists.

  DOI：

  10.1021/ja1048972
• 作为产物：
  描述：

  在 lithium hydroxide monohydrate 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 生成 4-(4-(trifluoromethoxy)phenyl)-4-pentenoic acid
  参考文献：
  名称：

  Asymmetric Bromolactonization Using Amino-thiocarbamate Catalyst

  摘要：

  A novel amino-thiocarbamate-catalyzed bromolactonization of unsaturated carboxylic acids has been developed. The scope of the reaction is evidenced by 22 examples of gamma-lactones with up to 99% yield and 93% ee. The protocol was applied in the enantioselective synthesis of the key intermediates of VLA-4 antagonists.

  DOI：

  10.1021/ja1048972

文献信息

• Enantioselective Bromolactonization Using an<i>S</i>-Alkyl Thiocarbamate Catalyst
  作者：Xiaojian Jiang、Chong Kiat Tan、Ling Zhou、Ying-Yeung Yeung

  DOI：10.1002/anie.201202079

  日期：2012.7.27

  The apple never falls far from the tree: S‐alkyl thiocarbamate 1 (see scheme, NBP=N‐bromophthalimide) was prepared in high yield through a synthetic sequence involving a Newman–Kwart rearrangement of the corresponding O‐alkyl thiocarbamates. Compound 1 was used to catalyze bromolactonization, thus providing enantioenriched δ‐lactones in excellent yield and enantioselectivity.

  苹果永远不会离树太远：通过涉及相应的O-烷基硫代氨基甲酸酯的Newman-Kwart重排的合成序列，以高收率制备了S-烷基硫代氨基甲酸酯1（参见方案，NBP = N-溴邻苯二甲酰亚胺）。化合物1用于催化溴化内酯化，从而以优异的收率和对映选择性提供了对映体富集的δ-内酯。
• Chiral Bifunctional Selenide Catalysts for Asymmetric Iodolactonizations
  作者：Ryuichi Nishiyori、Ken Okuno、Bun Chan、Seiji Shirakawa

  DOI：10.1248/cpb.c22-00049

  日期：2022.9.1

  BINOL-derived chiral sulfide catalysts unexpectedly gave iodolactonization products in nearly racemic forms. The roles of chalcogenide moieties and hydroxy groups on bifunctional catalysts were investigated, and the importance of both a selenide moiety and a hydroxy group on chiral bifunctional selenide catalysts to achieve enantioselective iodolactonizations was clarified. An optimized chiral bifunctional

  已知具有羟基的 1,1'-Bi-2-萘酚 (BINOL) 衍生的手性双功能硫化物和硒化物催化剂是对映选择性溴内酯化的有效催化剂。当应用于 4-戊烯酸的不对称碘内酯化时，这些催化剂会产生手性 γ-丁内酯产物，这些产物是药物化学中的重要化合物。尽管手性双功能硒化物在对映选择性碘内酯化中表现出良好的催化性能，但与 BINOL 衍生的手性硫化物催化剂的反应出乎意料地产生了几乎外消旋形式的碘内酯化产物。研究了硫属化物部分和羟基对双功能催化剂的作用，并阐明了手性双功能硒化物催化剂上的硒化物部分和羟基对实现对映选择性碘内酯化的重要性。将优化的手性双功能硒化物催化剂应用于手性 γ-丁内酯和苯酞的不对称合成。此外，手性双功能硒化物在 α,α-二烯丙基羧酸的催化对映选择性去对称碘内酯化中也得到了证明。 全尺寸图像
• Indole-Catalyzed Bromolactonization in Lipophilic Solvent: A Solid–Liquid Phase Transfer Approach
  作者：Tao Chen、Thomas Jian Yao Foo、Ying-Yeung Yeung

  DOI：10.1021/acscatal.5b01182

  日期：2015.8.7

  We have developed a novel indole-catalyzed bromolactonization of olefinic acids. The reaction could be conducted in lipophilic solvent through a solid liquid phase transfer mechanism. This catalytic protocol has been applied to the synthesis of base-sensitive bromolactones.