trans-[2-(3-methoxyphenyl)cyclopropane]carboxylic acid | 96728-38-0

• 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-(3-methoxyphenyl)cyclopropane]carboxylic acid
• 英文别名: (1S,2S)-2-(3-Methoxyphenyl)cyclopropane-1-carboxylic acid
• CAS: 96728-38-0
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: SEQTZPLHSZFWIY-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-(3-methoxyphenyl)cyclopropane]carboxylic acid 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 (1S,2S)-2-(3-Methoxy-phenyl)-cyclopropanecarbonyl chloride
  参考文献：
  名称：

  Total synthesis of aromatic steroids

  摘要：

  DOI：

  10.1021/jo00216a034
• 作为产物：
  描述：

  N-methoxy-N-methyl-trans-2-(3-methoxyphenyl)cyclopropanecarboxamide 在 potassium tert-butylate 作用下， 以 乙醚 为溶剂， 反应 16.0h， 以97%的产率得到trans-[2-(3-methoxyphenyl)cyclopropane]carboxylic acid
  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

文献信息

• Synthesis of new N-(arylcyclopropyl)acetamides and N-(arylvinyl)acetamides as conformationally-restricted ligands for melatonin receptors
  作者：Laurence Morellato、Marie Lefas-Le Gall、Michel Langlois、Daniel-Henri Caignard、Pierre Renard、Philippe Delagrange、Monique Mathé-Allainmat

  DOI：10.1016/j.bmcl.2012.11.069

  日期：2013.1

  N-(Arylcyclopropyl)acetamides and N-(arylvinyl)acetamides or methyl ureas have been prepared as constrained analogues of melatonin. The affinity of these new compounds for chicken brain melatonin receptors and recombinant human MT1 and MT2 receptors was evaluated using 2-[125I]-iodomelatonin as radioligand. Strict ethylenic or cyclopropyl analogues of the commercialized agonist agomelatine (Valdoxan®)

  已经制备了N-（芳基环丙基）乙酰胺和N-（芳基乙烯基）乙酰胺或甲基脲作为褪黑激素的约束类似物。这些新化合物对鸡脑褪黑激素受体以及重组人MT 1和MT 2受体的亲和力是通过使用2- [ 125 I]-碘降钙素作为放射性配体来评估的。在结合生物测定中，商业化激动剂阿戈美拉汀的严格的乙烯或环丙基类似物与阿戈美拉汀等效。然而，在黑色素聚集生物测定中，烯属类似物比环丙基之一更有效，但仍不如二取代的2,7-二甲氧基-萘烷化合物有效。
• New total synthesis of equilenin and estrone
  作者：Andrzej Robert Daniewski、Teresa Kowalczyk-Przewloka

  DOI：10.1016/s0040-4039(00)87355-4

  日期：1982.1

  The coupling of m-methoxystyrene () and diazoketone () over copper tartarate gave optically active (46% ee) cyclopropyl derivative (), which was converted into compounds or with 22% of optical induction.

  在酒石酸铜上将间甲氧基苯乙烯（）和重氮酮（）偶合，得到旋光性（46％ee）的环丙基衍生物（），将其转化为化合物或以22％的光诱导率转化。
• 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。
• Oxidative ring-opening of ferrocenylcyclopropylamines to N-ferrocenylmethyl β-hydroxyamides
  作者：Yi Sing Gee、Neils J. M. Goertz、Michael G. Gardiner、Christopher J. T. Hyland

  DOI：10.1039/c5ob02577j

  日期：——

  reduction of ferrocenyl cyclopropylimines to the corresponding amines triggers a facile oxidative ring-opening to yield the formal four-electron oxidation products: N-ferrocenylmethyl β-hydroxyamides. This process is believed to proceed via generation of a ferrocinium ion in the presence of air, leading to facile formation of a distonic radical cation that is ultimately trapped by oxygen.

  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。
• Exploring distal regions of the A3 adenosine receptor binding site: sterically constrained N6-(2-phenylethyl)adenosine derivatives as potent ligands
  作者：Susanna Tchilibon、Soo-Kyung Kim、Zhan-Guo Gao、Brian A Harris、Joshua B Blaustein、Ariel S Gross、Heng T Duong、Neli Melman、Kenneth A Jacobson

  DOI：10.1016/j.bmc.2004.02.037

  日期：2004.5

  putative A(3)AR binding site around the phenyl moiety. A heteroaromatic group (3-thienyl) could substitute for the phenyl moiety with retention of high affinity of A(3)AR binding. Other related N(6)-substituted adenosine derivatives were included for comparison. Although the N(6)-(2-phenyl-1-cyclopropyl) derivatives were full A(3)AR agonists, several other derivatives had greatly reduced efficacy. N(6)

  我们合成了N（6）-（1S，2R）-（2-苯基-1-环丙基）腺苷的苯环取代类似物，其与人A（3）AR的结合力强，Ki值为0.63 nM。测量了这些结构变化对人和大鼠腺苷受体的亲和力以及对hA（3）AR的内在功效的影响。3-硝基苯基类似物色谱分离成纯的非对映异构体，在A（3）AR结合中表现出10倍的立体选择性，有利于1S，2R异构体。分子模型在苯基部分周围的假定的A（3）AR结合位点中定义了疏水区（Phe168）。杂芳族基团（3-噻吩基）可以取代苯基部分，并保留A（3）AR结合的高亲和力。包括其他相关的N（6）取代腺苷衍生物进行比较。尽管N（6）-（2-苯基-1-环丙基）衍生物是完全的A（3）AR激动剂，但其他几种衍生物的功效也大大降低。N（6）-环丙基腺苷是一种A（3）AR拮抗剂，在环丙基部分的2位添加一个或两个苯环可恢复功效。N（6）-（2,2-二苯基乙基）腺苷是一种A（3）AR拮抗剂，