1,2,3,4-tetrahydro-1,4-methanonaphthalene-1-carboxylic acid | 13733-46-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2,3,4-tetrahydro-1,4-methanonaphthalene-1-carboxylic acid
• 英文别名: 1,4-Methanonaphthalene-1(2H)-carboxylic acid, 3,4-dihydro-；tricyclo[6.2.1.02,7]undeca-2,4,6-triene-1-carboxylic acid
• CAS: 13733-46-5
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: UMMVSVNWRMJICT-UHFFFAOYSA-N

物化性质

• 熔点：
  92-94 °C
• 沸点：
  349.1±21.0 °C(Predicted)
• 密度：
  1.325±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  1,2,3,4-tetrahydro-1,4-methanonaphthalene-1-carboxylic acid 在 五氯化磷 、 羟基甲苯磺酰碘苯 、 氨 、 potassium carbonate 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.75h， 生成 1-(3,4-Dihydro-2H-1,4-methano-naphthalen-1-yl)-piperidine
  参考文献：
  名称：

  Rigid Phencyclidine Analogues. Binding to the Phencyclidine and σ₁ Receptors

  摘要：

  Three phencyclidine (PCP) analogues possessing a highly rigid carbocyclic structure and an attached piperidine ring which is free to rotate were synthesized. Each analogue has a specific fixed orientation of the ammonium center of the piperidinium ring to the centrum of the phenyl ring. The binding affinities of the rigid analogues 1-piperidino-7,8-benzobicyclo[4.2.0]octene (14), 1-piperidinobenzobicyclo[2.2.1]heptene (16), and 1-piperidinobenzobicyclo[2.2.2]octene (13) for the PCP receptor ([H-3]TCP) and sigma-receptor (NANM) were determined. The three analogues show low to no affinity for the PCP receptor but good affinity for the sigma-receptor and can be considered sigma-receptor selective ligands with PCP/sigma ratios of 13, 293, and 368, respectively. The binding affinities for the sigma-receptor are rationalized in terms of a model for the sigma-pharmacophore.

  DOI：

  10.1021/jm970059p
• 作为产物：
  描述：

  Bicyclo<2.2.1>heptene-1-carboxylic acid 在 镍 氢氧化钾 、 硫酸 、 溴 作用下， 以 氯苯 、 邻二氯苯 为溶剂， 生成 1,2,3,4-tetrahydro-1,4-methanonaphthalene-1-carboxylic acid
  参考文献：
  名称：

  Benzonorbornene and derivatives. IV. Bridgehead and 1-carbinyl derivatives

  摘要：

  DOI：

  10.1021/jo00832a066

文献信息

• [EN] PI3K-α INHIBITORS AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS DE PI3K-α ET PROCÉDÉ D'UTILISATION DE CEUX-CI
  申请人：RELAY THERAPEUTICS INC

  公开号：WO2021222556A1

  公开（公告）日：2021-11-04

  The present disclosure relates to novel compounds and pharmaceutical compositions thereof, and methods for inhibiting the activity of PI3K-α enzymes with the compounds and compositions of the disclosure. The present disclosure further relates to, but is not limited to, methods for treating disorders associated with PI3K-α signaling with the compounds and compositions of the disclosure.

  本公开涉及新颖化合物及其制药组合物，以及利用本公开的化合物和组合物抑制PI3K-α酶活性的方法。本公开进一步涉及但不限于利用本公开的化合物和组合物治疗与PI3K-α信号相关的疾病的方法。
• Calcium independent camp phosphodiestrerase inhibitor antidepressant
  申请人：PFIZER INC.

  公开号：EP0247725A2

  公开（公告）日：1987-12-02

  Antidepressant agents having the formula wherein R1 is a polycycloalkyl group; R2 is methyl or ethyl, X is O or NH; and Y comprises a 5- or 6-membered heterocyclic ring having one or two nitrogens; or fused bicyclic heterocyclic rings having a total of three nitrogen atoms, one in each ring and one angular nitrogen.

  具有以下式子的抗抑郁剂 其中 R1 为多环烷基；R2 为甲基或乙基；X 为 O 或 NH；Y 为具有一个或两个氮原子的 5 或 6 元杂环；或具有总共三个氮原子的融合双环杂环，每个环中一个氮原子，一个角氮原子。
• Spectroscopy and Photochemistry of Phenylacetic Acid Esters and Related Substrates. The Stereoelectronic Dependence of the Aryl/Carboxyl Bichromophore Interaction
  作者：Annette M. Kasper、John J. Nash、Harry Morrison

  DOI：10.1021/jo00089a025

  日期：1994.5

  The 254-nm-initiated Norrish Type II photofragmentation of the ethoxyethyl esters of a series of phenylacetic acids (1b-4b) has been studied in order to further elaborate the aryl/ester interaction that is photochemically and photophysically evident in these systems. The ethoxyethyl ester of benzonorbornene-1-carboxylic acid (5) has also been prepared and studied, as has a rigid tricyclic lactone (6) which places the chromophores in an optimal stereoelectronic relationship for interaction. The experimental work is accompanied by Hartree-Fock (HF), Natural Bond Orbital (NBO), and Configuration Interaction with Single Excitations (CIS) calculations on the methyl esters of phenylacetic acid (1a) and alpha-methoxyphenylacetic acid (4a). The calculations confirm extensive through-space (TS) and through-bond (TB) interactions between the aryl and ester pi* orbitals but fail to provide conformational or electronic arguments to explain the unusually high reactivity of the alpha-methoxy series.
• Kasper Annette M., Nash John J., Morrison Harry, J. Org. Chem, 59 (1994) N 10, S 2792-2798
  作者：Kasper Annette M., Nash John J., Morrison Harry

  DOI：——

  日期：——
• US5128358A
  申请人：——

  公开号：US5128358A

  公开（公告）日：1992-07-07