3-菲甲酸 | 7470-14-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 3-菲甲酸
• 中文别名: 3-菲羧酸
• 英文名称: phenanthrene-3-carboxylic acid
• 英文别名: 3-Phenanthrenecarboxylic acid
• CAS: 7470-14-6
• 化学式: C₁₅H₁₀O₂
• 分子量: 222.243
• InChiKey: WYQIVZKSGGKUAX-UHFFFAOYSA-N

物化性质

• 熔点：
  270 °C
• 沸点：
  435.4±14.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（轻微）、甲醇（非常轻微，加热）

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2916399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  应存于室温、密封、干燥、避光的环境中。

反应信息

• 作为反应物：
  描述：

  3-菲甲酸 在 chromium(VI) oxide 、 18-冠醚-6 作用下， 以 aq. phosphate buffer 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 10.33h， 生成
  参考文献：
  名称：

  Visible Light-Initiated Bioorthogonal Photoclick Cycloaddition

  摘要：

  Here we report a visible light-triggered, catalyst free bioorthogonal reaction that proceeds via a distinct pathway from reported bioorthogonal reactions. The prototype of this bioorthogonal reaction was the photocycloaddition of 9,10-phenanthrenequinone with electron-rich alkenes to form fluorogenic [4+2] cycloadducts. The bioorthogonal photoclick cycloaddition was readily initiated using a conventional visible light source such as a hand-held LED lamp. The reaction proceeded rapidly under biocompatible conditions, without observable competition from side reactions such as nucleophilic additions by water or common nucleophilic species. The bioorthogonal functionality in this reaction did not cross react with various alkynes and electron-deficient alkenes such as monomethyl fumarate. We demonstrated orthogonal labeling of two proteins using this reaction together with a strain promoting azide-alkyne click reaction or the UV-triggered reaction of tetrazole with monomethyl fumarate. The application of this reaction in the temporal and spatial labeling of live cells was also demonstrated.

  DOI：

  10.1021/jacs.8b08175
• 作为产物：
  描述：

  (RS)-(1-naphthylmethyl)succinic acid 在 盐酸 、 氢氧化钾 、 氢氟酸 、 汞 、 锌 作用下， 以 二乙二醇 为溶剂， 生成 3-菲甲酸
  参考文献：
  名称：

  The Five Monocarboxylic Acids of Phenanthrene^1,2

  摘要：

  DOI：

  10.1021/jo01074a004

文献信息

• Synthesis and Pharmacology of <i>N</i>-Substituted Piperazine-2,3-dicarboxylic Acid Derivatives Acting as NMDA Receptor Antagonists
  作者：Richard M. Morley、Heong-Wai Tse、Bihua Feng、Jacqueline C. Miller、Daniel T. Monaghan、David E. Jane

  DOI：10.1021/jm0492498

  日期：2005.4.1

  The binding site for competitive NMDA receptor antagonists is on the NR2 subunit, of which there are four types (NR2A-D). Typical antagonists such as (R)-AP5 have a subunit selectivity of NR2A > NR2B > NR2C > NR2D. The competitive NMDA receptor antagonist (2R,3S)-(1-biphenylyl-4-carbonyl)piperazine-2,3-dicarboxylic acid (PBPD, 16b) displays an unusual selectivity with improved relative affinity for

  竞争性NMDA受体拮抗剂的结合位点位于NR2亚基上，其中有四种类型（NR2A-D）。典型的拮抗剂，例如（R）-AP5，具有亚单位选择性为NR2A> NR2B> NR2C> NR2D。竞争性NMDA受体拮抗剂（2R，3S）-（1-联苯基-4-羰基）哌嗪-2,3-二羧酸（PBPD，16b）与NR2A和NR2B相比，对NR2C和NR2D的相对亲和力增强，显示出非同寻常的选择性。合成了16b的带有芳基或芳基取代基的哌啶-2,3-二羧酸的N（1）连接基团的类似物，以探讨NR2C / NR2D选择性的结构要求。菲-2-羰基类似物16e对NR2C和NR2D的亲和力高> 60倍，对NR2C / NR2D的选择性是NR2A / NR2B的3-5倍。菲-3-羰基类似物（16f）的效力较低，但选择性更高，分别对NR2D的选择性是NR2A和NR2B的5倍和7倍。因此，带有大量疏水残基的拮抗剂具有与典型拮抗剂不同的NR2亚基选择性。
• Synthesis and structures of helical polycyclic aromatic hydrocarbons bearing aryl substituents at the most sterically hindered positions
  作者：Yanzhong Zhang、Jeffrey L. Petersen、Kung K. Wang

  DOI：10.1016/j.tet.2007.11.073

  日期：2008.2

  polycyclic aromatic hydrocarbons bearing one or two aryl substituents at the most sterically hindered positions to cause helical twists. The dynamic behaviors involving the helix inversion and the restricted rotation of the aryl substituents were investigated by temperature-dependent NMR studies. The X-ray structure of an indeno-fused 1-phenylpentahelicene derivative showed severe distortion of the [5]helicene

  建立了一个三步合成序列，从苯甲二烯二炔与芳基叔丁基酮之间的缩合反应开始，以使人们容易接近在最受阻位上带有一个或两个芳基取代基的有角稠合多环芳烃，从而引起螺旋扭曲。通过依赖于温度的NMR研究来研究涉及螺旋反转和芳基取代基的受限旋转的动力学行为。茚并稠合的1-苯基戊烯衍生物的X射线结构显示，[5]螺旋系统因平面度而严重变形。
• [EN] COMPOSITIONS AND METHODS OF MAKING EXPANDED HEMATOPOIETIC STEM CELLS USING PTEN INHIBITORS<br/>[FR] COMPOSITIONS ET MÉTHODES DE PRODUCTION DE CELLULES SOUCHES HÉMATOPOÏÉTIQUES EXPANSÉES À L'AIDE D'INHIBITEURS DE PTEN
  申请人：TRANSFUSION HEALTH LLC

  公开号：WO2018217567A1

  公开（公告）日：2018-11-29

  This invention is directed to, inter alia, compounds, methods, systems, and compositions for the maintenance, enhancement, and expansion of hematopoietic stem cells derived from sources of non-mobilized peripheral blood. Also provided herein are compounds of Formula I which are useful in maintaining, enhancing, and expanding of hematopoietic stem cells.

  本发明涉及一些方面，包括用于维持、增强和扩展非动员周围血源造血干细胞的化合物、方法、系统和组合物。本文还提供了一些公式I的化合物，这些化合物可用于维持、增强和扩展造血干细胞。
• A general method for the alkaline cleavage of enolisable ketones
  作者：Alenka Žabjek、Andrej Petrič

  DOI：10.1016/s0040-4039(99)01262-9

  日期：1999.8

  An efficient method is described for the cleavage of enolisable aryl methyl and aryl ethyl ketones using an excess of KOH in DMF at an elevated temperature. It presents a general hydrolytic method yielding aromatic carboxylic acids, and is complementary to the widely used oxidative methods for ketone cleavage.

  描述了一种在高温下使用过量的DOH中的KOH裂解可烯化的芳基甲基和芳基乙基酮的有效方法。它提供了一种产生芳族羧酸的常规水解方法，并且与广泛使用的氧化方法进行了裂解，这是对酮裂解的补充。
• Preparation of Polycyclic Azaarenes by an Extended Pomeranz-Fritsch Procedure
  作者：Michael Hewlins、Rhys Salter

  DOI：10.1055/s-2007-983744

  日期：——

  An extension of the Pomeranz-Fritsch procedure has been evaluated as a route to some polycyclic azaarenes. Aromatic aldehydes were treated with the dimethyl and diethyl acetals of 2-aminoethanal, the resulting imines reduced to amines which were tosylated and the resulting sulfonamides treated under a range of acidic conditions. The two naphthaldehydes led to benzo[f]isoquinoline and benzo[h]isoquinoline in overall yields of 13% and 36%. Phenanthrene-9-carbaldehyde and phenanthrene-3-carbaldehyde gave dibenzo[f,h]isoquinoline and naphtho[2,1-g]isoquinoline, respectively, as the major tetracyclic products. No pentacyclic product was obtained from a similar sequence starting from pyrene-1-carbaldehyde.

  对Pomeranz-Fritsch程序的扩展被评估为获得某些多环氮芳烃的一种途径。芳香醛与2-氨基乙醇的二甲基和二乙基缩醛反应，得到的亚胺还原为胺，然后进行托磺酰化，得到的磺酰胺在一系列酸性条件下处理。两种萘醛分别导致了苯并[f]异喹啉和苯并[h]异喹啉，总产率为13%和36%。菲-9-甲醛和菲-3-甲醛分别得到二苯并[f,h]异喹啉和萘并[2,1-g]异喹啉，作为主要的四环产品。从芘-1-甲醛出发的类似反应序列未能获得五环产品。