trans-2-(4-methoxyphenyl)cyclopropanecarboxylic acid | 110826-20-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: trans-2-(4-methoxyphenyl)cyclopropanecarboxylic acid
• 英文别名: (1S,2S)-2-(4-methoxyphenyl)cyclopropane-1-carboxylic acid
• CAS: 110826-20-5
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: CCTYOCDEILYYEF-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-2-(4-methoxyphenyl)cyclopropanecarboxylic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 苯 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Picosecond radical kinetics. Rate constants for ring openings of 2-aryl-substituted cyclopropylcarbinyl radicals

  摘要：

  The kinetics of ring openings of a series of eight (trans-2-arylcyclopropyl)methyl radicals (1) were studied by indirect kinetic methods using Barton's PTOC esters as radical precursors and reaction with PhSeH as the competition reaction. The substituents were CF3, F, Me, and OMe located on both the para and meta positions of the aromatic ring. Syntheses of the radical precursors and the products of the radical reactions are described. Kinetics were determined between -43 and 25 degrees C in four cases (CF, and OMe substituents) and at 0 and 25 degrees C in the other four cases. The rate constants at 25 degrees C ranged from 1.0 x 10(11) s(-1) (p-CH3) to 4.1 x 10(11) s(-1) (p-CF,). The relatively large acceleration of the p-CF3 group, ca. 2.5 times as fast as the parent system with Ar = Ph, correlates well with Adam's Delta D substituent parameters but not with other radical substituent parameters. These calibrated radical rearrangements provide a new set of ultrafast reactions that can be applied in mechanistic probe studies.

  DOI：

  10.1139/cjc-77-5-6-1123
• 作为产物：
  描述：

  反式-4-甲氧基肉桂酸 在 硫酸 、 sodium hydride 、 sodium hydroxide 作用下， 以 乙醇 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 134.0h， 生成 trans-2-(4-methoxyphenyl)cyclopropanecarboxylic acid
  参考文献：
  名称：

  二茂铁基环丙胺氧化成N-二茂铁基甲基β-羟基酰胺的†

  摘要：

  将二茂铁基环丙基亚胺原位还原为相应的胺会触发容易的氧化开环，从而产生正式的四电子氧化产物：N-二茂铁基甲基β-羟基酰胺。据信该过程是通过在空气存在下产生二茂铁离子来进行的，从而容易形成最终被氧捕获的二甲苯基自由基阳离子。

  DOI：

  10.1039/c5ob02577j

文献信息

• Difluoroacetaldehyde <i>N</i> ‐Triftosylhydrazone (DFHZ‐Tfs) as a Bench‐Stable Crystalline Diazo Surrogate for Diazoacetaldehyde and Difluorodiazoethane
  作者：Yongquan Ning、Xinyu Zhang、Yi Gai、Yuanqing Dong、Paramasivam Sivaguru、Yingying Wang、Bhoomireddy Rajendra Prasad Reddy、Giuseppe Zanoni、Xihe Bi

  DOI：10.1002/anie.202000119

  日期：2020.4.16

  study, we developed a bench-stable difluoroacetaldehyde N-triftosylhydrazone (DFHZ-Tfs) as an operationally safe diazo surrogate that can release in situ two low-molecular-weight diazoalkanes, diazoacetaldehyde (CHOCHN2 ) or difluorodiazoethane (CF2 HCHN2 ), in a controlled fashion under specific conditions. DFHZ-Tfs has been successfully employed in the Fe-catalyzed cyclopropanation and Doyle-Kirmse

  尽管挥发性官能化的重氮烷烃在有机合成中的重要性日益提高，但由于其难以处理以及存储和安全性问题，其安全生产和利用仍是一个艰巨的挑战。在这项研究中，我们开发了一种稳定的二氟乙醛N-三氟乙os（DFHZ-Tfs），作为一种操作安全的重氮替代物，可以原位释放两种低分子量的重氮烷烃，重氮乙醛（CHOCHN2）或二氟重氮乙烷（CF2 HCHN2）。在特定条件下的受控方式。DFHZ-Tfs已成功地用于铁催化的环丙烷化反应和Doyle-Kirmse反应中，从而突显了DFHZ-Tfs在有效构建包含CHO或CF2 H基团的分子框架中的合成效用。此外，
• [EN] PHENYLALANINE DERIVATIVES AND THEIR USE AS NON-PEPTIDE GLP-1 RECEPTOR MODULATORS<br/>[FR] DÉRIVÉS PHÉNYLALANINES ET LEUR UTILISATION COMME MODULATEURS NON PEPTIDIQUES DU RÉCEPTEUR DE GLP-1
  申请人：ARGUSINA INC

  公开号：WO2011094890A1

  公开（公告）日：2011-08-11

  Provided herein are non-peptide GLP-1 receptor modulator compounds, for example, of Formula (I), pharmaceutical compositions comprising such compounds, and processes of preparation thereof. Also provided are methods of their use for the treatment of a metabolic disorder.

  本文提供了非肽类GLP-1受体调节剂化合物，例如，Formula (I)的化合物，包括这些化合物的药物组合物，以及其制备方法。还提供了这些化合物用于治疗代谢紊乱的方法。
• The synergistic effect of copper chromite spinel nanoparticles (CuCr2O4) and basic ionic liquid on the synthesis of cyclopropanecarboxylic acids
  作者：Mohammad Hadi Ghasemi、Elaheh Kowsari

  DOI：10.1007/s11164-016-2572-1

  日期：2016.12

  Abstract An efficient synthesis of cyclopropanecarboxylic acids using copper chromite spinel nanoparticles and basic ionic liquid is described. In this study, a relatively simple method starting with trans-cinnamic acid for the synthesis of (±)-trans-2-phenylcyclopropanecarboxylic acid, a key intermediate in the synthesis of tranylcypromine sulfate as an active pharmaceutical ingredient, was employed

  摘要 描述了使用亚铬酸铜尖晶石纳米粒子和碱性离子液体有效合成环丙烷羧酸。在这项研究中，采用了一种相对简单的方法，该方法以反式肉桂酸为原料合成（±）-反式-2-苯基环丙烷羧酸，这是合成硫酸环丙亚胺作为活性药物的关键中间体。使用碱性离子液体[Bmim] OH和亚铬酸铜尖晶石纳米颗粒的组合作为催化体系，在四氢呋喃作为极性溶剂中可获得最佳结果。该方法是文献中描述的其他方法的有用替代方法。使用可商购的化学品，减少了环境危害，无需分离立体异构体，因此减少了总体步骤， 图形概要
• A novel approach to enantiopure cyclopropane compounds from biotransformation of nitrilesElectronic supplementary information (ESI) available: preparation of racemic nitrile, amides and acids; spectroscopic data of racemic nitriles; biotransformation of racemic amides; chiral HPLC analyses of nitriles, amides, acids and amines. See http://www.rsc.org/suppdata/nj/b2/b200110a/
  作者：Mei-Xiang Wang、Guo-Qiang Feng

  DOI：10.1039/b200110a

  日期：2002.10.30

  Rhodococcus sp. AJ270, a powerful and versatile nitrile hydratase/amidase containing microbial whole-cell system, catalyzed the enantioselective hydrolysis of both racemic trans- and cis-2-arylcyclopropanecarbonitriles to afford the corresponding amides and acids with enantiomeric excesses as high as >99%. The reaction rate and enantioselectivity observed for both nitrile hydratase and amidase were also strongly dependent upon the nature of the substituent and substitution pattern on the benzene ring of the substrates. The application of and the advantages of biotransformation of nitriles were demonstrated by preparing (1S,2R)-2-phenylcyclopropylamine and (1R,2R)-2-phenylcyclopropylmethylamine through facile and straightforward chemical manipulations of (1S,2S)-2-phenylcyclopropanecarboxylic acid and (1R,2R)-2-phenylcyclopropanecarboxamide, respectively.

  Rhodococcus sp. AJ270 是一种功能强大、用途广泛的腈水解酶/酰胺酶，含有微生物全细胞系统，可催化外消旋反式和顺式-2-芳基环丙烷甲腈的对映选择性水解，生成相应的酰胺和酸，对映过量高达 99%以上。腈水解酶和酰胺酶的反应速率和对映体选择性还与底物苯环上取代基的性质和取代模式密切相关。通过对(1S,2S)-2-苯基环丙烷羧酸和(1R,2R)-2-苯基环丙烷甲酰胺进行简单直接的化学处理，分别制备出(1S,2R)-2-苯基环丙胺和(1R,2R)-2-苯基环丙基甲胺，证明了腈类生物转化的应用和优势。
• Novel trans-2-aryl-cyclopropylamine analogues as potent and selective dipeptidyl peptidase IV inhibitors
  作者：Ting-Yueh Tsai、Tsu Hsu、Chiung-Tong Chen、Jai-Hong Cheng、Teng-Kuang Yeh、Xin Chen、Chung-Yu Huang、Chung-Nien Chang、Kai-Chia Yeh、Su-Huei Hsieh、Chia-Hui Chien、Yi-Wei Chang、Chih-Hsiang Huang、Yu-Wen Huang、Chen-Lung Huang、Ssu-Hui Wu、Min-Hsien Wang、Cheng-Tai Lu、Yu-Sheng Chao、Weir-Torn Jiaang

  DOI：10.1016/j.bmc.2009.02.020

  日期：2009.3

  DPP-IV. The structure-activity relationships (SAR) led to the discovery of novel series of DPP-IV inhibitors, having IC50 values of <100 nM with excellent selectivity over the closely related enzymes, DPP8, DPP-II and FAP. The studies identified a potent and selective DPP-IV inhibitor 24b, which exhibited the ability to both significantly inhibit plasma DPP-IV activity in rats and improve glucose tolerance

  合成了一系列反式-2-芳基-环丙胺衍生的化合物，并评估了其对DPP-IV的生物学活性。构效关系（SAR）导致发现了一系列新的DPP-IV抑制剂，其IC 50值<100 nM，对密切相关的酶DPP8，DPP-II和FAP具有优异的选择性。研究确定了一种有效的选择性DPP-IV抑制剂24b，该抑制剂具有显着抑制大鼠血浆DPP-IV活性并改善瘦小鼠和饮食诱发的肥胖小鼠对葡萄糖的耐受性的能力。