(1RS,2RS)-2-(3-Trifluoromethyl-phenyl)-cyclopropanecarboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1RS,2RS)-2-(3-Trifluoromethyl-phenyl)-cyclopropanecarboxylic acid ethyl ester
• 英文别名: ethyl (1S,2S)-2-[3-(trifluoromethyl)phenyl]cyclopropane-1-carboxylate
• 化学式: C₁₃H₁₃F₃O₂
• 分子量: 258.24
• InChiKey: KNSMQNROMFPXHH-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1RS,2RS)-2-(3-Trifluoromethyl-phenyl)-cyclopropanecarboxylic acid ethyl ester 在 lithium aluminium tetrahydride 作用下， 以 吡啶 、 乙醚 为溶剂， 反应 42.75h， 生成 4--4-methoxy-1-butene
  参考文献：
  名称：

  Arylcyclopropane photochemistry. Unusual aromatic substituent effects on the photochemical rearrangement of (2-arylcyclopropyl)methyl acetates to 1-arylhomoallyl acetates

  摘要：

  DOI：

  10.1021/ja00219a040
• 作为产物：
  描述：

  ethyl (E)-3-(3-(trifluoromethyl)phenyl)acrylate 、 (Diethylamino)dimethyloxosulfonium tetrafluoroborate 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 以29%的产率得到(1RS,2RS)-2-(3-Trifluoromethyl-phenyl)-cyclopropanecarboxylic acid ethyl ester
  参考文献：
  名称：

  Arylcyclopropane photochemistry. Unusual aromatic substituent effects on the photochemical rearrangement of (2-arylcyclopropyl)methyl acetates to 1-arylhomoallyl acetates

  摘要：

  DOI：

  10.1021/ja00219a040

文献信息

• CYCLOPROPYLBORONIC COMPOUNDS, METHOD FOR PREPARING SAME AND USE THEREOF
  申请人：DIVERCHIM

  公开号：US20150329566A1

  公开（公告）日：2015-11-19

  Cyclopropylboronic compounds, the preparation process thereof and the use thereof.

  环丙基硼化合物，其制备方法及用途。
• Solvolysis of 1-[<i>trans</i>-2-(<i>m</i>- or<i>p</i>-Substituted Phenyl)cyclopropyl]-1-methylethyl<i>p</i>-Nitrobenzoates
  作者：Yoshiaki Kusuyama

  DOI：10.1246/bcsj.71.685

  日期：1998.3

  value of r indicates the presence of the allylic cation intermediate where much more charge develops at the benzylic carbon for the derivatives with electron-donating substituents than is the case for the cyclopropylmethyl cation intermediate. Thus the solvolysis reaction proceeds via two independent pathways: one has a cyclopropyl cation intermediate and the ...

  研究了 1-[反式-2-（间或对取代苯基）环丙基]-1-甲基乙基对硝基苯甲酸酯在 80% 丙酮水溶液中的反应性和产物组成。对于反应性较低的取代基，如 m-Br、m-Cl 和 m-CF3，溶剂分解产物是相应的 2-(2-芳基环丙基)-2-丙醇，表明是环丙基甲基阳离子中间体。随着取代基给电子能力的增加，开环产物增加。Yukawa-Tsuno 方程对反应性的应用提供了 -1.43 的 ρ 值和 0.59 的 r 值，相关系数为 0.997。较大的 r 值表明存在烯丙基阳离子中间体，其中具有给电子取代基的衍生物在苄基碳上产生的电荷比环丙基甲基阳离子中间体多得多。因此，溶剂分解反应通过两种独立的途径进行：一种是环丙基阳离子中间体，另一种是...
• Repurposing a Nitric Oxide Transport Hemoprotein Nitrophorin 2 for Olefin Cyclopropanation
  作者：Shunzhi Huang、Wen-Hao Deng、Rong-Zhen Liao、Chunmao He

  DOI：10.1021/acscatal.2c03515

  日期：2022.11.4

  repurposed for catalyzing abiological carbene transfer reactions. Herein, we rationally designed an engineered variant of nitrophorin 2 (NP2)─a nitric oxide transport hemoprotein─that catalyzes olefin cyclopropanation with high activity and stereoselectivity. Being a β-barrel protein, the engineered NP2 variant showed a unique substrate preference, in contrast to the mainstream α-helical carbene-transfer

  越来越多的血红素蛋白最近被重新用于催化非生物卡宾转移反应。在这里，我们合理地设计了一种工程化的 nitrophorin 2 (NP2)——一种一氧化氮转运血红蛋白——以高活性和立体选择性催化烯烃环丙烷化。作为一种 β-桶蛋白，工程 NP2 变体显示出独特的底物偏好，与主流的 α-螺旋卡宾转移血红素酶（如细胞色素 P450 酶和肌红蛋白）形成对比。催化反应可以在制备规模上进行，同时保持立体选择性。量子化学计算进一步支持了 NP2 催化的苯乙烯环丙烷化的立体选择性，并阐明了关键残基的重要性。像这样，
• Selective 5-Hydroxytryptamine 2C Receptor Agonists Derived from the Lead Compound Tranylcypromine: Identification of Drugs with Antidepressant-Like Action
  作者：Sung Jin Cho、Niels H. Jensen、Toru Kurome、Sudhakar Kadari、Michael L. Manzano、Jessica E. Malberg、Barbara Caldarone、Bryan L. Roth、Alan P. Kozikowski

  DOI：10.1021/jm801354e

  日期：2009.4.9

  We report here the design, synthesis, and pharmacological properties of a series of compounds related to tranylcypromine (9), which itself was discovered as a lead compound in a high-throughput screening campaign. Starting from 9, which shows modest activity as a 5-HT2C agonist, a series of 1-aminomethyl-2-phenylcyclopropanes was investigated as 5-HT2C agonists through iterative structural modifications. Key pharmacophore feature of this new class of ligands is a 2-aminomethyl-trans-cyclopropyl side chain attached to a substituted benzene ring. Among the tested compounds, several were potent and efficacious 5-HT2C receptor agonists with selectivity over both 5-HT2A and 5-HT2B receptors in functional assays. The most promising compound is 37, with 120- and 14-fold selectivity over 5-HT2A and 5-HT2B, respectively (EC50 = 585, 65, and 4.8 nM at the 2A, 2B, and 2C subtypes, respectively). In animal studies, compound 37 (10-60 mg/kg) decreased immobility time in the mouse forced swim test.
• COMPOSES CYCLOPROPYLBORONIQUES, LEUR PROCEDE DE PREPARATION ET LEUR UTILISATION
  申请人：Diverchim

  公开号：EP2931708B1

  公开（公告）日：2017-05-10