2-(4-(trifluoromethyl)phenyl)piperidine | 526182-95-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-(4-(trifluoromethyl)phenyl)piperidine
• 英文别名: 2-[4-(Trifluoromethyl)phenyl]piperidine
• CAS: 526182-95-6
• 化学式: C₁₂H₁₄F₃N
• mdl: MFCD05190075
• 分子量: 229.245
• InChiKey: BPIPNPGHOKSKPH-UHFFFAOYSA-N

物化性质

• 沸点：
  274.0±40.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-(trifluoromethyl)phenyl)piperidine 在 正丁基锂 、 2,2,2-三氟苯乙酮 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 0.17h， 生成 C₁₂H₁₂F₃N
  参考文献：
  名称：

  未受保护的脂环胺的区域选择性 α-氰化

  摘要：

  通过将 TMSCN 添加到相应的亚胺上，脂环族仲胺转化为 α-氨基腈，亚胺是通过用简单的酮氧化剂氧化胺衍生的氨基锂而原位产生的中间体。具有现有 α-取代基的胺会发生区域选择性 α'-氰化，即使该位点的 C-H 键活性较低。胺α-芳基化可以与α'-氰化结合，在一次操作中生成双官能化产物。

  DOI：

  10.1021/acs.orglett.2c02148
• 作为产物：
  描述：

  1-Boc-2-哌啶酮 在 sodium tetrahydroborate 、 碘 、 magnesium 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 生成 2-(4-(trifluoromethyl)phenyl)piperidine
  参考文献：
  名称：

  A One-Pot Process for the Enantioselective Synthesis of Amines via Reductive Amination under Transfer Hydrogenation Conditions

  摘要：

  Cyclic amines may be prepared via a sequence of deprotection followed by intramolecular reductive amination of t-Boc-protected amino ketones under asymmetric transfer hydrogenation conditions. In cases where the corresponding imine reaction proceeds with high enantioselectivity, this is reflected in the one-step process.

  DOI：

  10.1021/ol035746r

文献信息

• A General Catalyst Based on Cobalt Core–Shell Nanoparticles for the Hydrogenation of N‐Heteroarenes Including Pyridines
  作者：Kathiravan Murugesan、Vishwas G. Chandrashekhar、Carsten Kreyenschulte、Matthias Beller、Rajenahally V. Jagadeesh

  DOI：10.1002/anie.202004674

  日期：2020.9.28

  core–shell based nanoparticles prepared by template synthesis of cobalt‐pyromellitic acid on silica and subsequent pyrolysis. The optimal catalyst material allows for general and selective hydrogenation of pyridines, quinolines, and other heteroarenes including acridine, phenanthroline, naphthyridine, quinoxaline, imidazo[1,2‐a]pyridine, and indole under comparably mild reaction conditions. In addition

  在此，我们报道了通过二氧化硅上钴均苯四酸的模板合成和随后的热解制备的特定二氧化硅负载的Co/Co 3 O 4核壳纳米粒子的合成。最佳的催化剂材料允许在相对温和的反应条件下对吡啶、喹啉和其他杂芳烃（包括吖啶、菲咯啉、萘啶、喹喔啉、咪唑并[1,2-a]吡啶和吲哚）进行全面和选择性氢化。此外，还展示了这些钴纳米颗粒的回收利用及其脱氢催化能力。
• Borenium-Catalyzed Reduction of Pyridines through the Combined Action of Hydrogen and Hydrosilane
  作者：Joshua J. Clarke、Yuuki Maekawa、Masakazu Nambo、Cathleen M. Crudden

  DOI：10.1021/acs.orglett.1c01892

  日期：2021.9.3

  Mesoionic carbene-stabilized borenium ions efficiently reduce substituted pyridines to piperidines in the presence of a hydrosilane and a hydrogen atmosphere. Control experiments and deuterium labeling studies demonstrate reversible hydrosilylation of the pyridine, enabling full reduction of the N-heterocycle under milder conditions. The silane is a critical reaction component to prevent adduct formation

  在氢硅烷和氢气氛的存在下，介离子卡宾稳定的硼离子有效地将取代的吡啶还原为哌啶。对照实验和氘标记研究证明了吡啶的可逆氢化硅烷化，能够在较温和的条件下完全还原 N-杂环。硅烷是防止哌啶产物和硼催化剂之间形成加合物的关键反应组分。
• [EN] BENZOXAZEPINES AS INHIBITORS OF PI3K/m TOR AND METHODS OF THEIR USE AND MANUFACTURE<br/>[FR] BENZOXAZÉPINES COMME INHIBITEURS DE PI3K/M TOR, MÉTHODES D'UTILISATION ET DE FABRICATION BENZOXAZEPINES AS INHIBITORS OF PI3K/M TOR AND METHODS OF THEIR USE AND MANUFACTURE
  申请人：EXELIXIS INC

  公开号：WO2010138487A1

  公开（公告）日：2010-12-02

  The invention is directed to Compounds of Formula (I): the invention provides compounds that inhibit, regulate, and/or modulate P13K and/or mTOR that are useful in the treatment of hyperproliferative diseases, such as cancer, in mammals. This invention also provides methods of making the compound methods of using such compounds in the treatment of hyperproliferative diseases in mammals, especially humans, and to pharmaceutical compositions containing such compounds. For example, cancer in which activity against PI3fC-alph mTOR, or both contributes to its pathology and/or symptomatology include breast cancer mantle cell lymphoma, renal cell carcinoma, acute myelogenous leukemia, chronic myelogenous leukemia, NPM/ALK- transformed anaplastic large cell lymphoma, diffu large B cell lymphoma, rhabdomyosarcoma, ovarian cancer, endometrial cancer, cervic cancer, non small cell lung carcinoma, small cell lung carcinoma, adenocarcinoma, col cancer, rectal cancer, gastric carcinoma, hepatocellular carcinoma, melanoma, pancreat cancer, prostate carcinoma, thyroid carcinoma, anaplastic large cell lymphoma, hemangiom glioblastoma, or head and neck cancer.

  这项发明涉及式(I)的化合物：该发明提供了抑制、调节和/或调节P13K和/或mTOR的化合物，这些化合物在治疗哺乳动物的高增殖性疾病，如癌症，方面非常有用。该发明还提供了制备该化合物的方法，以及在治疗哺乳动物，特别是人类的高增殖性疾病中使用这些化合物的方法，以及含有这些化合物的药物组合物。例如，对PI3fC-α mTOR或两者都具有活性有助于其病理学和/或症状学的癌症包括乳腺癌、套细胞淋巴瘤、肾细胞癌、急性髓细胞白血病、慢性髓细胞白血病、NPM/ALK转化的间变性大细胞淋巴瘤、弥漫性大B细胞淋巴瘤、横纹肌肉瘤、卵巢癌、子宫内膜癌、宫颈癌、非小细胞肺癌、小细胞肺癌、腺癌、结肠癌、直肠癌、胃癌、肝细胞癌、黑色素瘤、胰腺癌、前列腺癌、甲状腺癌、间变性大细胞淋巴瘤、血管瘤、胶质母细胞瘤或头颈癌。
• The identification of a novel lead class for phosphodiesterase 2 inhibition by fragment-based drug design
  作者：Ashley B. Forster、Pravien Abeywickrema、Jaime Bunda、Christopher D. Cox、Tamara D. Cabalu、Melissa Egbertson、John Fay、Krista Getty、Dawn Hall、Maria Kornienko、Jun Lu、Gopal Parthasarathy、John Reid、Sujata Sharma、William D. Shipe、Sean M. Smith、Stephen Soisson、Shawn J. Stachel、Hua-Poo Su、Deping Wang、Richard Berger

  DOI：10.1016/j.bmcl.2017.10.054

  日期：2017.12

  identified a novel PDE2 inhibitor series using fragment-based screening. Pyrazolopyrimidine fragment 1, while possessing weak potency (Ki = 22.4 μM), exhibited good binding efficiencies (LBE = 0.49, LLE = 4.48) to serve as a start for structure-based drug design. With the assistance of molecular modeling and X-ray crystallography, this fragment was developed into a series of potent PDE2 inhibitors with good

  我们已经使用基于片段的筛选确定了一种新型的PDE2抑制剂系列。吡唑并嘧啶片段1具有很弱的效价（K i  = 22.4μM），但表现出良好的结合效率（LBE = 0.49，LLE = 4.48），可以作为基于结构的药物设计的起点。借助分子建模和X射线晶体学，该片段被开发为一系列具有良好理化性质的有效PDE2抑制剂。鉴定出表现出有利的大鼠药代动力学性质的化合物16（一种PDE2选择性抑制剂）。
• Benzoxazepines as Inhibitors of PI3K/mTOR and Methods of Their Use and Manufacture
  申请人：Aay Naing

  公开号：US20120258953A1

  公开（公告）日：2012-10-11

  The invention is directed to Compounds of Formula (I): the invention provides compounds that inhibit, regulate, and/or modulate P13K and/or mTOR that are useful in the treatment of hyperproliferative diseases, such as cancer, in mammals. This invention also provides methods of making the compound methods of using such compounds in the treatment of hyperproliferative diseases in mammals, especially humans, and to pharmaceutical compositions containing such compounds. For example, cancer in which activity against PI3fC-alph mTOR, or both contributes to its pathology and/or symptomatology include breast cancer mantle cell lymphoma, renal cell carcinoma, acute myelogenous leukemia, chronic myelogenous leukemia, NPM/ALK-transformed anaplastic large cell lymphoma, diffu large B cell lymphoma, rhabdomyosarcoma, ovarian cancer, endometrial cancer, cervic cancer, non small cell lung carcinoma, small cell lung carcinoma, adenocarcinoma, col cancer, rectal cancer, gastric carcinoma, hepatocellular carcinoma, melanoma, pancreat cancer, prostate carcinoma, thyroid carcinoma, anaplastic large cell lymphoma, hemangiom glioblastoma, or head and neck cancer.

  本发明涉及化合物I式的化合物：本发明提供了一种抑制、调节和/或调节P13K和/或mTOR的化合物，其在哺乳动物中治疗增殖过度性疾病，如癌症方面非常有用。本发明还提供了制备该化合物的方法，使用这些化合物在哺乳动物中治疗增殖过度性疾病的方法，特别是人类，并提供了包含这些化合物的制药组合物。例如，对于活性针对PI3fC-alph mTOR或两者都对其病理和/或症状学产生贡献的癌症，包括乳腺癌、曼托细胞淋巴瘤、肾细胞癌、急性髓性白血病、慢性髓性白血病、NPM / ALK转化的间变性大细胞淋巴瘤、弥漫性大B细胞淋巴瘤、横纹肌肉瘤、卵巢癌、子宫内膜癌、宫颈癌、非小细胞肺癌、小细胞肺癌、腺癌、结肠癌、直肠癌、胃癌、肝细胞癌、黑色素瘤、胰腺癌、前列腺癌、甲状腺癌、间变性大细胞淋巴瘤、血管瘤、胶质母细胞瘤或头颈癌。