2-(hydroxymethyl)-1-phenylcyclopropane-1-carboxylic acid | 70209-83-5

• 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: 2-(hydroxymethyl)-1-phenylcyclopropane-1-carboxylic acid
• CAS: 70209-83-5
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: PSMORJXEGALFGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1S,5R)-1-苯基-3-氧杂双环[3.1.0]己-2-酮 在 Cunninghamella blakesleeana 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 以32%的产率得到(1S5R)-1-苯基-3-氧杂双环[3.1.0]己烷-2-酮（左米那普仑中间体A）
  参考文献：
  名称：

  微生物转化34：参与抗抑郁米那普仑的合成中的关键内酯的对映选择性水解®

  摘要：

  一个关键内酯允许抗抑郁药米那普仑的合成的对映选择性水解®中描述。筛选了几种生物催化剂以实现这种生物转化，使用真菌白僵菌和枯草杉木的全细胞培养物获得了最好的结果。

  DOI：

  10.1016/0040-4039(96)00872-6

文献信息

• [EN] CYCLOPROPYL DERIVATIVES AS NK3 RECEPTOR ANTAGONISTS<br/>[FR] DERIVES DE CYCLOPROPYLE UTILISES COMME ANTAGONISTES DU RECEPTEUR DE NK3
  申请人：LUNDBECK & CO AS H

  公开号：WO2005016884A1

  公开（公告）日：2005-02-24

  The present invention relates to cyclopropyl derivatives of formula (I) and salt thereof. These compounds are NK3 receptor antagonists and may therefore be useful for treatment of diseases where the NK3 receptor is implicated, e.g. psychotic disorders.

  本发明涉及式(I)的环丙基衍生物及其盐。这些化合物是NK3受体拮抗剂，因此可能对涉及NK3受体的疾病，如精神障碍，具有治疗作用。
• AMINOALKYLCYCLOPROPANE DERIVATIVE
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：EP0747348A1

  公开（公告）日：1996-12-11

  Disclosed are a novel optically active compound represented by formula (1), a racemic modification thereof, and a pharmaceutically acceptable acid addition salt of the optically active compound or racemic modification thereof:    wherein R is a straight chain or branched C1-C5 aliphatic group which is saturated or unsaturated, or a phenyl group which is unsubstituted or substituted with 1 to 3 substituents which are each independently selected from the group consisting of a halogen atom, a C1-C4 alkyl group, a nitro group, an amino group, a hydroxyl group and a C1-C4 alkoxy group; and mark * indicates an asymmetric carbon atom. The novel optically active aminoalkylcyclopropane derivative of the present invention, a racemic modification thereof, and a pharmaceutically acceptable acid addition salt of the optically active aminoalkylcyclopropane derivative or racemic modification thereof have remarkably high antagonistic activity with respect to NMDA receptor, as compared to known aminomethylcyclopropane derivatives and is useful as a preventive agent for cerebral infarction and a protective agent against ischemic diseases.

  本发明公开了一种由式（1）代表的新型光学活性化合物、其外消旋修饰物以及该光学活性化合物或其外消旋修饰物的药学上可接受的酸加成盐： 其中 R 是饱和或不饱和的直链或支链 C1-C5 脂肪族基团，或未被取代或被 1 至 3 个取代基取代的苯基，这些取代基各自独立地选自卤素原子、C1-C4 烷基、硝基、氨基、羟基和 C1-C4 烷氧基组成的组；标记 * 表示不对称碳原子。 与已知的氨基甲基环丙烷衍生物相比，本发明的新型光学活性氨基烷基环丙烷衍生物、其外消旋修饰物以及光学活性氨基烷基环丙烷衍生物或其外消旋修饰物的药学上可接受的酸加成盐对 NMDA 受体具有显著的高拮抗活性，可用作脑梗塞的预防剂和缺血性疾病的保护剂。
• METHOD FOR PRODUCING 2-OXO-1-PHENYL-3-OXABICYCLO¬3.1.0|HEXANE
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1757597A1

  公开（公告）日：2007-02-28

  The present invention provides a process for producing 2-oxo-1-phenyl-3-oxabicyclo[3.1.0]hexane which comprises reacting phenylacetonitrile with epichlorohydrin in the presence of sodium hydride. According to the present invention, 2-oxo-1-phenyl-3-oxabicyclo[3.1.0]hexane can be produced safely, easily and industrially advantageously.

  本发明提供了一种生产 2-氧代-1-苯基-3-氧杂二环[3.1.0]己烷的工艺，该工艺包括在氢化钠存在下使苯乙腈与环氧氯丙烷反应。 根据本发明，2-氧代-1-苯基-3-氧杂二环[3.1.0]己烷的生产安全、简便且具有工业优势。
• Stereocontrolled Synthesis of Trisubstituted Cyclopropanes:  Expedient, Atom-Economical, Asymmetric Syntheses of (+)-Bicifadine and DOV21947
  作者：Feng Xu、Jerry A. Murry、Bryon Simmons、Edward Corley、Kenneth Fitch、Sandor Karady、David Tschaen

  DOI：10.1021/ol061650w

  日期：2006.8.1

  An expedient, atom-economical, asymmetric synthesis of 1-aryl-3-azabicyclo[3.1.0]hexanes, including (+)-Bicifadine and DOV21947, in a single-stage through process without isolation of any intermediates has been developed. The key of this synthesis is the in-depth mechanistic understanding of the complicated epoxy nitrile coupling at each reaction stage. Therefore, the desired trisubstituted cyclopropane can be prepared in high ee and yield by controlling the reaction pathway through manipulating the nitrile anion aggregation state.
• Cyclopropane-1,2-dicarboxylic acids as new tools for the biophysical investigation of<i>O</i>-acetylserine sulfhydrylases by fluorimetric methods and saturation transfer difference (STD) NMR
  作者：Giannamaria Annunziato、Marco Pieroni、Roberto Benoni、Barbara Campanini、Thelma A. Pertinhez、Chiara Pecchini、Agostino Bruno、Joana Magalhães、Stefano Bettati、Nina Franko、Andrea Mozzarelli、Gabriele Costantino

  DOI：10.1080/14756366.2016.1218486

  日期：2016.11.4

  Cysteine is a building block for many biomolecules that are crucial for living organisms. O-Acetylserine sulfhydrylase (OASS), present in bacteria and plants but absent in mammals, catalyzes the last step of cysteine biosynthesis. This enzyme has been deeply investigated because, beside the biosynthesis of cysteine, it exerts a series of "moonlighting" activities in bacteria. We have previously reported a series of molecules capable of inhibiting Salmonella typhimurium (S. typhymurium) OASS isoforms at nanomolar concentrations, using a combination of computational and spectroscopic approaches. The cyclopropane-1,2-dicarboxylic acids presented herein provide further insights into the binding mode of small molecules to OASS enzymes. Saturation transfer difference NMR (STD-NMR) was used to characterize the molecule/ enzyme interactions for both OASS-A and B. Most of the compounds induce a several fold increase in fluorescence emission of the pyridoxal 5'-phosphate (PLP) coenzyme upon binding to either OASS-A or OASS-B, making these compounds excellent tools for the development of competition-binding experiments.