3-(4-sec-butylphenyl)propanoic acid | 900027-16-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-(4-sec-butylphenyl)propanoic acid
• 英文别名: 4-(1-Methylpropyl)benzenepropanoic acid；3-(4-butan-2-ylphenyl)propanoic acid
• CAS: 900027-16-9
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: STEVVENVZQIWON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-sec-butylphenyl)propanoic acid 在 氯化亚砜 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 7-(sec-butyl)-4-methylchroman-2-one
  参考文献：
  名称：

  3-芳基丙酸直接氧化环化为3,4-二氢香豆素：反应机理的重新研究

  摘要：

  在气味分子嗅觉分析的启发下，通过 2D NMR 和 X 射线分析对 3-芳基丙酸基于 PIFA 的氧化环化制备的 3,4-二氢香豆素的组成进行了修正。在计算分析的支持下，中间体螺内酯阳离子的迁移机制得到了修正：选择性地获得了1,2-烷基位移而不是1,2-羧基位移。

  DOI：

  10.1021/acs.joc.3c02645
• 作为产物：
  描述：

  methyl 3-(4-sec-butylphenyl)propanoate 在 lithium hydroxide 、 水 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以100%的产率得到3-(4-sec-butylphenyl)propanoic acid
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel diarylalkyl amides as TRPV1 antagonists

  摘要：

  We have developed a new class of diarylalkyl amides as novel TRPV1 antagonists. They exhibited potent Ca-45(2+) uptake inhibitions in rat DRG neuron. In particular, the amide 59 was identified as a potent antagonist with IC50 of 57 nM. The synthesis and structure-activity relationship of the diarylalkyl amides are also described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.010

文献信息

• SPIROCYCLIC COMPOUNDS AS TRYPTOPHAN HYDROXYLASE INHIBITORS
  申请人：Karos Pharmaceuticals, Inc.

  公开号：US20170095476A1

  公开（公告）日：2017-04-06

  The present invention is directed to spirocyclic compounds which are inhibitors of tryptophan hydroxylase (TPH), particularly isoform 1 (TPH1), that are useful in the treatment of diseases or disorders associated with peripheral serotonin including, for example, gastrointestinal, cardiovascular, pulmonary, inflammatory, metabolic, and low bone mass diseases, as well as serotonin syndrome, and cancer.
• US5777151A
  申请人：——

  公开号：US5777151A

  公开（公告）日：1998-07-07
• US9750740B2
  申请人：——

  公开号：US9750740B2

  公开（公告）日：2017-09-05
• Design, synthesis, and biological evaluation of novel diarylalkyl amides as TRPV1 antagonists
  作者：Fu-Nan Li、Nam-Jung Kim、Seung-Mann Paek、Do-Yeon Kwon、Kyung Hoon Min、Yeon-Su Jeong、Sun-Young Kim、Young-Ho Park、Hee-Doo Kim、Hyeung-Geun Park、Young-Ger Suh

  DOI：10.1016/j.bmc.2009.04.010

  日期：2009.5

  We have developed a new class of diarylalkyl amides as novel TRPV1 antagonists. They exhibited potent Ca-45(2+) uptake inhibitions in rat DRG neuron. In particular, the amide 59 was identified as a potent antagonist with IC50 of 57 nM. The synthesis and structure-activity relationship of the diarylalkyl amides are also described. (C) 2009 Elsevier Ltd. All rights reserved.
• Direct Oxidative Cyclization of 3-Arylpropionic Acids to 3,4-Dihydrocoumarins: Reinvestigation of the Reaction Mechanism
  作者：Huiyi Zeng、Zihao Ye、An Chai、You Jiang、Yue Zou、Fanhong Wu、Zhiming Li、Lijun Zhou

  DOI：10.1021/acs.joc.3c02645

  日期：2024.4.19

  Instigated by olfactory analysis of odorant molecules, the constitutions of 3,4-dihydrocoumarins prepared by PIFA-based oxidative cyclizations of 3-arylpropionic acids were revised by means of 2D NMR and X-ray analysis. Supported by computational analysis, the migratory mechanism of intermediate spirolactonic cations has been amended: 1,2-alkyl shifts instead of 1,2-carboxylic shifts were selectively obtained

  在气味分子嗅觉分析的启发下，通过 2D NMR 和 X 射线分析对 3-芳基丙酸基于 PIFA 的氧化环化制备的 3,4-二氢香豆素的组成进行了修正。在计算分析的支持下，中间体螺内酯阳离子的迁移机制得到了修正：选择性地获得了1,2-烷基位移而不是1,2-羧基位移。