(1R,2S)-trans-2-phenylcyclohexylamine | 69743-67-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1R,2S)-trans-2-phenylcyclohexylamine
• 英文别名: (-)-(1R,2S)-2-Phenylcyclohexanamine；(1R,2S)-2-phenylcyclohexanamine；1r-Amino-2t-phenyl-cyclohexan；trans-2-Phenyl-cyclohexylamin；trans-2-Phenylcyclohexylamin；cis-2-Phenylcyclohexylamin；(1R,2S)-2-phenylcyclohexan-1-amine
• CAS: 69743-67-5
• 化学式: C₁₂H₁₇N
• 分子量: 175.274
• InChiKey: KLJIPLWGNJQJRM-NWDGAFQWSA-N

物化性质

• 熔点：
  43.5-44 °C
• 沸点：
  278.6±29.0 °C(Predicted)
• 密度：
  0.983±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 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：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,2S)-trans-2-phenylcyclohexylamine 在 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 生成 4-anilino-1-[(1R,2S)-2-phenylcyclohexyl]piperidine-4-carbonitrile
  参考文献：
  名称：

  Discovery of N-(2-aryl-cyclohexyl) substituted spiropiperidines as a novel class of GlyT1 inhibitors

  摘要：

  Screening of the Roche compound library led to the identification of cis-N-(2-phenyt-cyclohexyl)-spiropiperidine 1 as structurally novel GlyT1 inhibitor. The SAR, which was developed in this series, resulted in the discovery of highly potent compounds displaying excellent selectivity against the GlyT2 isoform. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.075
• 作为产物：
  描述：

  phenyl-1 aza-7 bicyclo<4.1.0>heptane 在 镍 氢气 作用下， 以 乙醇 为溶剂， 生成 (1R,2S)-trans-2-phenylcyclohexylamine
  参考文献：
  名称：

  1-苯基双环[4.1.0]庚烷及其相应的叠氮和环氧化物的催化氢解反应

  摘要：

  1-苯基双环[4.1.0]庚烷（1a），顺式-1-苯基-2-甲基双环[4.1.0]庚烷（1b），1-苯基-7-氮杂双环[4.1.0]庚烷（2）的氢解反应以Ni，Pd，Rh和Pt为催化剂，研究了1-苯基-7-氧杂双环[4.1.0]庚烷（3）。的C的氢解1 C 7的键1A和1B导致的选择性形成反式-1-苯基-2-甲基环己烷（图4a）与配置的保持。化合物1a不仅给出4a，而且还给出了苯基环庚烷（6a），其是C中的产物1 C 6键裂变，和的比图6a到图4a的序列中增加：RH <铂镍⪡钯。没有C 1 C 6中的氢解中观察到键裂变1b中。这些结果可以通过涉及形成π-苄基络合物的机理来解释。

  DOI：

  10.1016/s0040-4020(01)97213-8

文献信息

• Organoboranes for synthesis. 7. An improved general synthesis of primary amines from alkenes via hydroboration-organoborane chemistry
  作者：Herbert C Brown、Kee-Won Kim、Morris Srebnik、Singaram Bakthan

  DOI：10.1016/s0040-4020(01)83445-1

  日期：——

  Triorganylboranes, R3B, and diorganylborinic esters, R2BOR', react readily with preformed chloramine or hydroxylamine-0-sulfonic acid to produce the corresponding primary amines, RNH2. However, the product of the reaction following hydrolysis is the boronic acid, RB(OH)2, limiting the yield to 67% for R3B and to 50% for R2BOR'. This problem has now been overcome with the help of lithium dimethylborohydride

  Triorganylboranes，R 3 B，和diorganylborinic酯，R 2 BOR”，具有预制氯胺或羟胺容易反应0磺酸，以产生相应的伯胺，RNH 2。但是，水解后反应的产物是硼酸RB（OH）2，R 3 B的产率限制为67 ％，R 2 BOR'的产率限制为50％。现在已经借助二甲基硼氢化锂克服了这个问题，该二甲基硼氢化锂易于原位转化为二甲基硼烷。代表性烯烃通过二甲基硼烷进行氢硼化提供相应的单有机基二甲基硼烷RMe 2B.用羟胺-O-磺酸处理该中间体提供所需的胺RNH 2，分离产率为73％至95％。反应在完全保留的情况下进行，从而再现了有机硼烷RMe 2 B中有机基团的精确结构。
• [EN] TRIAZA-SPIROPIPERIDINE DERIVATIVES FOR USE AS GLYT-1 INHIBITORS IN THE TREATMENT OF NEUROLOGICAL AND NEUROPSYCHIATRIC DISORDERS<br/>[FR] DERIVES DE TRIAZA-SPIROPIPERIDINE A UTILISER COMME INHIBITEURS DE GLYT-1 DANS LE TRAITEMENT DE TROUBLES NEUROLOGIQUES ET NEUROPSYCHIATRIQUES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2005040166A1

  公开（公告）日：2005-05-06

  The invention relates to compounds of the general formula (I), wherein A-A is -CH2-CH2-, -CH2-CH2-CH2-, -CH2-0- or -0-CH2-; x is hydrogen or hydroxy; R1 is aryl or heteroaryl, unsubstituted or substituted by one or more substituents, selected from the group consisting of lower alkyl, lower alkoxy, halogen or trifluoromethyl; R2 is aryl or heteroaryl, unsubstituted or substituted by one or more substituents, selected from the group consisting of lower alkyl, lower alkoxy, halogen or trifluoromethyl, or is lower alkyl, -(CH2)n-­cycloalkyl, -(CH2)n-CF3, -(CH2)p-0-lower alkyl, -(CH2)1,2-phenyl, optionally substituted by halogen, lower alkyl, lower alkoxy or trifluoromethyl, or is -(CH2)p-NRR', wherein W and R' form together with the N-atom a heterocyclic ring, selected from the group consisting of piperidine, morpholine, thiomorpholine or 1, I-dioxo thiomorpholine; R3, R4 are independently from each other hydrogen, lower alkyl, phenyl or benzyl; R5 is hydrogen, lower alkyl or benzyl; R6 is hydrogen or lower alkyl; n is 0, 1 or 2; and p is 2 or 3; and to pharmaceutically acceptable acid addition salts thereof for the treatment of psychoses, pain, neurodegenerative disfunction in memory and learning, schizophrenia, dementia and other diseases in which cognitive processes are impaired, such as attention deficit disorders or Alzheimer's disease.

  该发明涉及一般式(I)的化合物，其中A-A为-CH2-CH2-，-CH2-CH2-CH2-，-CH2-0-或-0-CH2-；x为氢或羟基；R1为芳基或杂环芳基，未取代或由一个或多个取代基取代，所选取自较低烷基、较低烷氧基、卤素或三氟甲基的群组；R2为芳基或杂环芳基，未取代或由一个或多个取代基取代，所选取自较低烷基、较低烷氧基、卤素或三氟甲基的群组，或为较低烷基、-(CH2)n-环烷基、-(CH2)n-CF3、-(CH2)p-0-较低烷基、-(CH2)1,2-苯基，或者可由卤素、较低烷基、较低烷氧基或三氟甲基取代的苯基，或为-(CH2)p-NRR'，其中W和R'与N原子一起形成选自哌啶、吗啉、硫代吗啉或1,1-二氧硫代吗啉的杂环环的环；R3、R4相互独立为氢、较低烷基、苯基或苄基；R5为氢、较低烷基或苄基；R6为氢或较低烷基；n为0、1或2；p为2或3；以及其药用可接受的酸盐，用于治疗精神病、疼痛、记忆和学习中的神经退行性功能障碍、精神分裂症、痴呆症和其他认知过程受损的疾病，如注意力缺陷障碍或阿尔茨海默病。
• [EN] 3-ARYL AND HETEROARYL SUBSTITUTED 5-TRIFLUOROMETHYL OXADIAZOLES AS HISTONE DEACETYLASE 6 (HDAC6) INHIBITORS<br/>[FR] 5-TRIFLUOROMÉTHYL-OXADIAZOLES SUBSTITUÉS EN 3-ARYLE ET HÉTÉROARYLE EN TANT QU'INHIBITEURS DE L'HISTONE DÉSACÉTYLASE 6 (HDAC6)
  申请人：MERCK SHARP & DOHME

  公开号：WO2017222951A1

  公开（公告）日：2017-12-28

  The present invention is directed to substituted 5-trifluoromethyl oxadiazole compounds of generic formula (I) or a pharmaceutically acceptable salt thereof. In particular, the invention is directed to a class of aryl and heteroaryl substituted 5-trifluoromethyl oxadiazole compounds of formula I which may be useful as HDAC6 inhibitors for treating cellular proliferative diseases, including cancer, neurodegenerative diseases, such as schizophrenia and stroke, as well as other diseases.

  本发明涉及通式（I）的取代5-三氟甲基噁二唑化合物或其药学上可接受的盐。具体而言，本发明涉及一类芳基和杂环芳基取代的通式I的5-三氟甲基噁二唑化合物，可能作为HDAC6抑制剂用于治疗细胞增殖性疾病，包括癌症、神经退行性疾病（如精神分裂症和中风）以及其他疾病。
• Novel guanidinobenzamides
  申请人：——

  公开号：US20020137939A1

  公开（公告）日：2002-09-26

  Compounds of formula IA and IB are new 1 where the variables R 1 through R 10 have the values set forth herein. Such compounds have use in treating diseases such as obesity and type II diabetes, and may be provided as pharmaceutical formulations in conjunction with a pharmaceutically acceptable carrier.

  公式IA和IB的化合物是新的，其中变量R1到R10具有以下数值。这些化合物在治疗肥胖和2型糖尿病等疾病方面具有用途，并可作为与药学上可接受的载体结合的药物制剂提供。
• A Method for Determining Absolute Configuration of Cycloalkanamines and Related Compounds by CD Spectra of Their 2,4-Dinitrophenyl Derivatives
  作者：Masao Kawai、Teruhiko Iwase、Yasuo Butsugan、Ukon Nagai

  DOI：10.1246/bcsj.58.304

  日期：1985.1

  and related compounds having an amino and an aromatic groups in vicinal positions were prepared. Their CD spectra exhibited marked Cotton effect around 400 nm, the sign of which was shown to coincide with the chirality between the two chromophore-bearing bonds. This relation, as a special example of exciton chirality method, is useful for determining absolute configuration of cyclic compounds having

  制备了环烷胺的 N-(2,4-二硝基苯基)衍生物和在邻位具有氨基和芳族基团的相关化合物。他们的 CD 光谱在 400 nm 附近表现出明显的棉花效应，其符号显示与两个带发色团的键之间的手性一致。这种关系作为激子手性方法的一个特例，可用于确定具有伯氨基的环状化合物的绝对构型。