(-)-(1R,2R)-trans-1-aminomethyl-2-phenylcyclopropane | 301861-27-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (-)-(1R,2R)-trans-1-aminomethyl-2-phenylcyclopropane
• 英文别名: trans-(R,R)-(2-phenylcyclopropyl)methylamine；(-)-(1R,2R)-2-phenylcyclopropylmethylamine；trans-1-Aminomethyl-2-phenyl-cyclopropan；[(1R,2R)-2-phenylcyclopropyl]methanamine
• CAS: 301861-27-8
• 化学式: C₁₀H₁₃N
• 分子量: 147.22
• InChiKey: ATTLDOZXPZCOGK-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (-)-(1R,2R)-trans-1-aminomethyl-2-phenylcyclopropane 以45%的产率得到
  参考文献：
  名称：

  BORNE R. F.; FORRESTER M. L.; WATERS I. W., J. MED. CHEM. , 1977, 20, NO 6, 771-776

  摘要：

  DOI：
• 作为产物：
  描述：

  trans-2-phenylcyclopropanecarbonitrile 在 lithium aluminium tetrahydride 、 Rhodococcus sp. AJ₂₇₀ 作用下， 以 phosphate buffer 为溶剂， 反应 1.0h， 生成 (-)-(1R,2R)-trans-1-aminomethyl-2-phenylcyclopropane
  参考文献：
  名称：

  Enantioselective synthesis of chiral cyclopropane compounds through microbial transformations of trans-2-arylcyclopropanecarbonitriles

  摘要：

  Enantioselective biotransformations of racemic trans-2-arylcyclopropanecarbonitriles catalyzed by Rhodococcus sp. AJ270 cells proceeded efficiently to give good to excellent optical yields of (-)-(1R,2R)-2-arylcyclopropanecarboxamides and (+)-(1S,21S)-2-arylcyclopropanecarboxylic acids, which were converted into optically active cyclopropylmethylamine and cyclopropylamine derivatives upon reduction and the Curtius rearrangement. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01031-5

文献信息

• 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。
• 5-HT2C Receptor Agonists as Anorectic Agents
  申请人：Kozikowski Alan

  公开号：US20090203750A1

  公开（公告）日：2009-08-13

  This invention relates to compounds which modulate receptors of the 5-HT2 family of receptors, and particularly to compounds which modulate 5-HT2C receptors. Compounds of the invention include agonists and selective agonists for the 5-HT2C receptor Compounds of the invention include selective agonists for the 5-HT2C receptor which exhibit significantly less or no agonist activity on the 5-HT2A receptor and/or the 5-HT2B receptor. Compounds of this invention are those of Formula I and pharmaceutically acceptable salts, esters and solvates (including hydrates) wherein variables are defined in the specification hereof.

  本发明涉及调节5-HT2家族受体的化合物，特别是调节5-HT2C受体的化合物。本发明的化合物包括5-HT2C受体的激动剂和选择性激动剂。本发明的化合物包括5-HT2C受体的选择性激动剂，其在5-HT2A受体和/或5-HT2B受体上表现出显著较少或无激动剂活性。本发明的化合物包括式I和药学上可接受的盐、酯和溶剂（包括水合物），其中变量在本规范中定义。
• Transition-Metal-Free C–N Cross-Coupling Enabled by a Multifunctional Reagent
  作者：Patrick S. Fier、Suhong Kim

  DOI：10.1021/jacs.4c00871

  日期：2024.3.13

  cross-coupling reaction of phenols and primary amines using a simple and readily available multifunctional reagent. The reactions work by induced proximity and electronic activation of both the nucleophile and the electrophile for net dehydrative C–N coupling reactions. Notably, the reactions do not involve the use of a transition metal for C–N bond formation, preactivation of the phenol electrophile, or exclusion

  我们报告了使用简单且易于获得的多功能试剂设计和开发了酚和伯胺的无过渡金属交叉偶联反应。该反应通过亲核试剂和亲电子试剂的诱导接近和电子激活来进行净脱水 C-N 偶联反应。值得注意的是，这些反应不涉及使用过渡金属形成 C-N 键、酚亲电子试剂的预活化或排除空气或湿气。温和的条件可以耐受多种官能团，并使其能够应用于具有多种偶联伙伴的复杂底物的后期功能化。
• 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.
• US7309799B2
  申请人：——

  公开号：US7309799B2

  公开（公告）日：2007-12-18