methyl (E)-2-(3-phenylprop-1-en-1-yl)benzoate | 1027255-60-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: methyl (E)-2-(3-phenylprop-1-en-1-yl)benzoate
• 英文别名: methyl 2-[(E)-3-phenylprop-1-enyl]benzoate
• CAS: 1027255-60-2
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: GXFZAAVETZAOBY-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (E)-2-(3-phenylprop-1-en-1-yl)benzoate 在 5percent Pd/C sodium hydroxide 、 氢气 作用下， 以 甲醇 、 乙醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、250.0 kPa 条件下， 反应 15.67h， 生成 2-(3-Phenylpropyl)benzoic acid
  参考文献：
  名称：

  4-Aminoquinolines:  Novel Nociceptin Antagonists with Analgesic Activity

  摘要：

  Small-molecule nociceptin antagonists were synthesized to examine their therapeutic potential. After a 4-aminoquinoline derivative was found to bind with the human ORL1 receptor, a series of 4-aminoquinolines and related compounds were synthesized and their binding was evaluated. Elucidation of structure-activity relationships eventually led to the optimum compounds. One of the se compounds, N-(4-amino-2-methylquinolin-6-yl) -2-(4-ethylphenoxymethyl)benzamide hydrochloride (11) not only antagonized nociceptin-induced allodynia in mice but also showed analgesic effect in a hot plate test using mice and in a formalin test using rats. Its analgesic effect was not antagonized by the opioid antagonist naloxone. These results indicate that this nociceptin antagonist has the potential to become a novel type of analgesic that differs from mu -opioid agonists.

  DOI：

  10.1021/jm0002073
• 作为产物：
  描述：

  邻溴苯甲酸甲酯 、 (E)-4,4,5,5-tetramethyl-2-(3-phenylprop-1-en-1-yl)-1,3,2-dioxaborolane 在 potassium phosphate 、 XPhos Pd G2 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 17.0h， 以98%的产率得到methyl (E)-2-(3-phenylprop-1-en-1-yl)benzoate
  参考文献：
  名称：

  使用亲核氟化物源进行对映选择性催化氟内酯化反应

  摘要：

  报道了通过手性芳基碘化物催化的氟内酯化反应对映选择性合成 4-氟异色满酮。该方法使用 HF-吡啶作为亲核氟化物源与过酸化学计量氧化剂，并以高对映和非对映选择性提供含有含氟立体中心的内酯。在这些内酯化反应中观察到的区域选择性与通过已建立的不对称亲电氟化方案获得的区域选择性是互补的。

  DOI：

  10.1021/jacs.6b09499

文献信息

• 4-Aminoquinolines:  Novel Nociceptin Antagonists with Analgesic Activity
  作者：Hisashi Shinkai、Takao Ito、Tetsuya Iida、Yuki Kitao、Hideki Yamada、Itsuo Uchida

  DOI：10.1021/jm0002073

  日期：2000.11.1

  Small-molecule nociceptin antagonists were synthesized to examine their therapeutic potential. After a 4-aminoquinoline derivative was found to bind with the human ORL1 receptor, a series of 4-aminoquinolines and related compounds were synthesized and their binding was evaluated. Elucidation of structure-activity relationships eventually led to the optimum compounds. One of the se compounds, N-(4-amino-2-methylquinolin-6-yl) -2-(4-ethylphenoxymethyl)benzamide hydrochloride (11) not only antagonized nociceptin-induced allodynia in mice but also showed analgesic effect in a hot plate test using mice and in a formalin test using rats. Its analgesic effect was not antagonized by the opioid antagonist naloxone. These results indicate that this nociceptin antagonist has the potential to become a novel type of analgesic that differs from mu -opioid agonists.
• Enantioselective, Catalytic Fluorolactonization Reactions with a Nucleophilic Fluoride Source
  作者：Eric M. Woerly、Steven M. Banik、Eric N. Jacobsen

  DOI：10.1021/jacs.6b09499

  日期：2016.10.26

  fluoride source with a peracid stoichiometric oxidant and provides access to lactones containing fluorine-bearing stereogenic centers in high enantio- and diastereoselectivity. The regioselectivity observed in these lactonization reactions is complementary to that obtained with established asymmetric electrophilic fluorination protocols.

  报道了通过手性芳基碘化物催化的氟内酯化反应对映选择性合成 4-氟异色满酮。该方法使用 HF-吡啶作为亲核氟化物源与过酸化学计量氧化剂，并以高对映和非对映选择性提供含有含氟立体中心的内酯。在这些内酯化反应中观察到的区域选择性与通过已建立的不对称亲电氟化方案获得的区域选择性是互补的。