2,5-二苯基戊酸 | 22055-24-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2,5-二苯基戊酸
• 英文名称: 2,5-diphenylvaleric acid
• 英文别名: 2,5-diphenyl-valeric acid；2,5-Diphenyl-valeriansaeure；α.δ-Diphenyl-butan-α-carbonsaeure；α.δ-Diphenyl-n-valeriansaeure；2,5-Diphenylvaleriansaeure；I+/--Phenylbenzenepentanoic acid；2,5-diphenylpentanoic acid
• CAS: 22055-24-9
• 化学式: C₁₇H₁₈O₂
• 分子量: 254.329
• InChiKey: CGWQWPYMNKHMMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-二苯基戊酸 在 氯化亚砜 作用下， 以 苯 为溶剂， 生成 N,N-Diethyl-2,5-diphenylvaleramide
  参考文献：
  名称：

  Vejdelek,Z.J.; Protiva,M., Collection of Czechoslovak Chemical Communications, 1971, vol. 36, p. 1611 - 1623

  摘要：

  DOI：
• 作为产物：
  描述：

  4-hydroxy-2,5-diphenyl-valeric acid 在 氢碘酸 作用下， 生成 2,5-二苯基戊酸
  参考文献：
  名称：

  Spiegel, Chemische Berichte, 1882, vol. 15, p. 1548

  摘要：

  DOI：

文献信息

• Agents acting on the central nervous system. Synthesis of 3-phenyl-2-piperazinyl-1-benzazocines, 3-substituted-2-piperazinyl-1-benzazepines and related compounds.
  作者：KATSUHIKO HINO、YASUTAKA NAGAI、HITOSHI UNO

  DOI：10.1248/cpb.36.2386

  日期：——

  Three series of compounds, 3-phenyl-5, 6-dihydro-1-benzazocines (7-9), 3-methyl-5H-1-benzazepines. (15-20) and 3-phenyl-4, 5-dihydro-3H-1- benzazepines (24-35), having a 2-(1-piperazinyl) group, were synthesized, and their pharmacological effects on the central nervous system were evaluated in mice. Among them, 3-methyl- (15-18) and 3-phenyl-4, 5-dihydro-2-piperazinylbenzazepines (26 and 33-35) showed mild anti-reserpine activity. However, no significant anti-exploratory, anti-maximal electroshock seizure or anti-tremorine activity was generally found.Novel ring transformations of α-chlorolactams are also described. The reaction of the 3-chloro-3-phenyl-2, 3, 4, 5-tetrahydro-1H-1-benzazepin-2-ones (37a, b) and benzazocinone analogs (46a, b) with piperidine or various piperazines resulted in ring contraction to give the 2-phenyl-1, 2, 3, 4-tetrahydroquinoline-2-carbozamides (38-41) and the analogous benzazepine-2-carboxamides (47 and 48), respectively. The reaction of analogous 3-chloro-3-methylbenzazepinone (14a) with potassium carbonate in methanol also resulted in similar ring transformation to give methyl tetrahydroquinoline-2-carboxylate (50). These rearrangements were supposed to proceed via the azirinone intermediate.

  合成了三类化合物，包括3-苯基-5,6-二氢-1-苯并唑啉（7-9）、3-甲基-5H-1-苯并氮烯（15-20）和3-苯基-4,5-二氢-3H-1-苯并氮烯（24-35），它们具有2-(1-哌嗪基)基团，并对小鼠的中枢神经系统进行药理学评估。其中，3-甲基-（15-18）和3-苯基-4,5-二氢-2-哌嗪基苯并氮烯（26和33-35）表现出轻微的抗雷沙平活性。然而，普遍未发现显著的抗探索、抗最大电休克癫痫或抗颤震活性。同时，还描述了α-氯内酯的新环转化。3-氯-3-苯基-2,3,4,5-四氢-1H-1-苯并氮烯-2-酮（37a, b）和苯并唑啉酮类似物（46a, b）与哌啶或各种哌嗪的反应导致环收缩，生成2-苯基-1,2,3,4-四氢喹啉-2-羧酰胺（38-41）和相应的苯并氮烯-2-羧酰胺（47和48）。类似的3-氯-3-甲基苯并氮烯酮（14a）与碳酸钾在甲醇中的反应也产生了类似的环转化，生成甲基四氢喹啉-2-羧酸酯（50）。这些重排被认为是通过吡咯唑中间体进行的。
• Electrophotochemical Metal‐Catalyzed Enantioselective Decarboxylative Cyanation
  作者：Kai Yang、Yukang Wang、Sanzhong Luo、Niankai Fu

  DOI：10.1002/chem.202203962

  日期：——

  reaction conditions for radical decarboxylation to produce alkyl radicals, which could be effectively intercepted by asymmetric electrochemical Cu catalysis for the construction of C−CN bonds in a highly stereoselective manner.

  开发了一种可持续且高效的电光化学金属催化方案，用于将现成的脂肪族羧酸直接转化为手性烷基腈。电光化学 Ce 催化能够在温和的反应条件下自由基脱羧产生烷基自由基，其可以被不对称电化学 Cu 催化有效拦截，以高度立体选择性的方式构建 C-CN 键。
• Copper-Catalyzed Enantioselective Decarboxylative Cyanation of Benzylic Acids Promoted by Hypervalent Iodine(III) Reagents
  作者：Zhaoxia Li、Guang’an Zhang、Yue Song、Miaomiao Li、Zhongxian Li、Wei Ding、Junliang Wu

  DOI：10.1021/acs.orglett.3c00816

  日期：2023.5.5

  directly decarboxylative cyanation reactions of common alkyl carboxylic acids remain largely elusive. Herein, we report a protocol for copper-catalyzed direct and enantioselective decarboxylative cyanation of benzylic acids. The in situ activation of acid substrates by a commercially inexpensive hypervalent iodine(III) reagent promoted the yield of the alkyl radicals under mild reaction conditions without

  铜催化的不对称自由基氰化反应已成为快速构建 α-手性腈的有力策略。然而，普通烷基羧酸的直接脱羧氰化反应在很大程度上仍然难以捉摸。在此，我们报告了一种用于铜催化的苄酸直接和对映选择性脱羧氰化的方案。通过商业上廉价的高价碘 (III) 试剂原位激活酸性底物，在温和的反应条件下促进了烷基自由基的产率，而无需预官能化。结构多样的手性烷基腈以良好的收率和高对映选择性生产。此外，手性产物可以通过进一步的转化很容易地转化为其他有用的手性化合物。
• Novel anilide derivatives of substituted arylacetic acids
  申请人：SUMITOMO PHARMACEUTICALS COMPANY, LIMITED

  公开号：EP0184822A2

  公开（公告）日：1986-06-18

  A compound of the formula I: wherein Ar is a heterocyclic group or an aromatic hydrocarbon group optionally having one or two substituents selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 alkoxy, nitro, cyano, di(C1-C4) alkylamino, benzyloxy, hydroxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl and C1-C4 alkanoylamino, X is a hydroxyl group or either one of the following groups: (in which R2, R3, R4 and R5 are each independently hydrogen or C1-C4 alkyl or, when R2 and R3 or R4 and R5 are taken together with the adjacent nitrogen atom to which they are attached, they represent pyrrolidino, piperidino, morpholino, N-(C1-C4)-alkylpiperazino or N-phenylpipera- zino), R is an aromatic hydrocarbon or heterocyclic group and n is an integer of 1 to 4, or its acid addition salt, which is useful as a cerebral metabolism stimulant or a nootropic agent.

  式 I 的化合物 其中 Ar 是杂环基团或芳香烃基团，可任选具有一个或两个选自卤素、C1-C4 烷基、C1-C4 烷氧基、硝基、氰基、二(C1-C4)烷基氨基、苄氧基、羟基、C1-C4 烷硫基、C1-C4 烷基亚磺酰基、C1-C4 烷基磺酰基和 C1-C4 烷酰氨基组成的取代基，X 是羟基或下列基团之一： (其中 R2、R3、R4 和 R5 各自独立地为氢或 C1-C4 烷基，或当 R2 和 R3 或 R4 和 R5 与它们所连接的相邻氮原子合在一起时，它们代表吡咯烷基、哌啶基、吗啉基、N-(C1-C4)-烷基哌嗪基或 N-苯基哌嗪基），R 为芳香烃或杂环基，n 为 1 至 4 的整数时，或其酸加成盐，可用作脑代谢刺激剂或神经营养剂。
• Remote Construction of N‐Heterocycles via 1,4‐Palladium Shift‐Mediated Double C−H Activation
  作者：Takeru Miyakoshi、Nadja E. Niggli、Olivier Baudoin

  DOI：10.1002/anie.202116101

  日期：2022.4.19

  AbstractIn the past years, Pd0‐catalyzed C(sp3)−H activation provided efficient and step‐economical methods to synthesize carbo‐ and heterocycles via direct C(sp2)−C(sp3) bond formation. We report herein that a 1,4‐Pd shift allows access to N‐heterocycles which are difficult to build via a direct reaction. It is shown thato‐bromo‐N‐methylanilines undergo a 1,4‐Pd shift at theN‐methyl group, followed by intramolecular trapping by C(sp2)−H or C(sp3)−H activation at another nitrogen substituent and remote C−C bond formation to generate biologically relevant isoindolines and β‐lactams. The product selectivity is influenced by the employed ligand, with NHCs favoring the product of remote C−C coupling against products arising from direct C−C coupling and N‐demethylation.