2-(methylsulfonyl)-1,2,3,4-tetrahydroisoquinoline | 35612-82-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 2-(methylsulfonyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: N-methylsulphonyl-1,2,3,4-tetrahydroisoquinoline；2-methanesulfonyl-1,2,3,4-tetrahydro-isoquinoline；N-Methylsulfonyl-1,2,3,4-tetrahydroisochinolin；2-Mesyl-6,7-dimethoxytetrahydroisochinolin；2-methylsulfonyl-3,4-dihydro-1H-isoquinoline
• CAS: 35612-82-9
• 化学式: C₁₀H₁₃NO₂S
• mdl: MFCD00113991
• 分子量: 211.285
• InChiKey: FKKMAKWPSSRSFE-UHFFFAOYSA-N

物化性质

• 熔点：
  129-130 °C(Solv: benzene (71-43-2))
• 沸点：
  357.1±52.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(methylsulfonyl)-1,2,3,4-tetrahydroisoquinoline 、 对氟苯甲酸甲酯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以78%的产率得到2-((3,4-dihydroisoquinolin-2(1H)-yl)sulfonyl)-1-(4-fluorophenyl)ethan-1-one
  参考文献：
  名称：

  Hepatoselectivity of statins: Design and synthesis of 4-sulfamoyl pyrroles as HMG-CoA reductase inhibitors

  摘要：

  4-Sulfamoyl pyrroles were designed as novel hepatoselective HMG-CoA reductase inhibitors (statins) to reduce myalgia, a statin-induced adverse effect. The compounds were prepared via a [3 + 2] cycloaddition of a Munchnone with a sulfonamide-substituted alkyne. We identified compounds with greater selectivity for hepatocytes compared to L6-myocytes than rosuvastatin and atorvastatin. There was an inverse correlation of myocyte potencies and ClogP values. A number of analogs were effective at reducing cholesterol in acute and chronic in vivo models but they lacked sufficient chronic in vivo activity to warrant further development. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.124
• 作为产物：
  描述：

  N-benzyl-N-(β-bromoethyl)sulfonamide 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 以33%的产率得到2-(methylsulfonyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Aromatic Cyclizatons of b-Aminoethyl Radicals and a-Carbamolymethyl Radicals. ortho-Substitution vs. ipso-Substitution

  摘要：

  DOI：

  10.3987/com-90-5559

文献信息

• JANUS KINASE INHIBITOR COMPOUNDS AND METHODS
  申请人：GOODACRE SIMON CHARLES

  公开号：US20100317643A1

  公开（公告）日：2010-12-16

  The invention provides compounds of Formula I, stereoisomers or pharmaceutically acceptable salts thereof, wherein A, B, D, R 1 , R 2 , R 4 and R 5 are defined herein, a pharmaceutical composition that includes a compound of Formula I and methods of use thereof

  这项发明提供了公式I的化合物，其立体异构体或药学上可接受的盐，其中A、B、D、R1、R2、R4和R5在此处被定义，包括公式I化合物的药物组合物以及其使用方法
• Conformational equilibria due to ring inversion in N-alkyl-cis-decahydroisoquinolines
  作者：Judith M. Bailey、Harold Booth、Hatif A. R. Y. Al-Shirayda

  DOI：10.1039/p29840000583

  日期：——

  The position of conformational equilibria due to ring inversion in N-alkyl-cis-decahydroisoquinolines (alkyl = Me, Et, Pri, CH2CF3, or CH2CCl3) has been assessed directly from 13C and/or 19F n.m.r. spectra recorded at temperatures between 173 and 253 K. The measured equilibrium constants are related to the inductive effect of the N-substituent which produces an increase (Me, Et, Pri) or decrease (CH2CF3

  已直接从13 C和/或19 F中评估了N-烷基-顺式-十氢异喹啉（烷基= Me，Et，Pr i，CH 2 CF 3或CH 2 CCl 3）中由于环反转引起的构象平衡位置。在173和253 K之间的温度下记录的nmr光谱。测得的平衡常数与N取代基的感应作用有关，该感应作用产生增加（Me，Et，Pr i）或减少（CH 2 CF 3，CH 2 CCl 3））的大小gauche丙胺型排斥反应。将经历交换的两个双椅构象的碳原子的13 C化学位移列表化。
• Synthesis of no-carrier-added [11C]methanesulfonyl chloride as a new labeling agent for PET radiopharmaceutical development
  作者：Julie A. McCarron、Victor W. Pike

  DOI：10.1002/jlcr.745

  日期：2003.10.31

  sodium hydrogen sulfide for subsequent treatment with either chlorinated water (route 2) or over heated manganese(IV) oxide and then calcium hypochlorite (route 3). These procedures gave NCA [11C]mesyl chloride in 77% (route 2) and 28% (route 3) RCYs from [11C]iodomethane at about 20 min from ERP. Crude [11C]mesyl chloride, produced by route 2 or 3, reacted rapidly with THIQ to give the corresponding NCA

  描述了使用无载体添加 (NCA) 碳 11（t1/2=20.4 分钟；β+=99.8%）标记甲磺酰（甲磺酰）氯的三种方法，以提供一种在放射性药物开发中具有潜在价值的新标记剂正电子发射断层扫描 (PET)。每种方法都使用 NCA [11C] 碘甲烷，它很容易通过已知程序从回旋加速器产生的 [11C] 二氧化碳或 [11C] 甲烷中制备。第一种方法（路线 1）包括将 [11C] 碘甲烷转化为 [11C] 甲基锂，然后用磺酰氯处理。在放射性核素生产 (ERP) 结束后 30 分钟，从 [11C] 碘甲烷中以 78% 的衰减校正放射化学产率 (RCY) 获得 NCA [11C] 甲磺酰氯。然而，正丁烷磺酰氯的共同生产限制了该标记剂与 1,2,3,4-四氢异喹啉 (THIQ) 的反应程度。设计了两种新的合成方法，基于通过加热的硫化氢钠将 [11C] 碘甲烷转化为 [11C] 甲硫醇，然后用氯化水（路线
• Heteroaryl substituted pyrrolo[2,3-b]pyridines and pyrrolo[2,3-b]pyrimidines as janus kinase inhibitors
  申请人：Rodgers D. James

  公开号：US20070135461A1

  公开（公告）日：2007-06-14

  The present invention provides heteroaryl substituted pyrrolo[2,3-b]pyridines and heteroaryl substituted pyrrolo[2,3-b]pyrimidines that modulate the activity of Janus kinases and are useful in the treatment of diseases related to activity of Janus kinases including, for example, immune-related diseases, skin disorders, myeloid proliferative disorders, cancer, and other diseases.

  本发明提供了杂环取代的吡咯并[2,3-b]吡啶和杂环取代的吡咯并[2,3-b]嘧啶，可以调节雅努斯激酶的活性，并且在治疗与雅努斯激酶活性相关的疾病中具有用处，例如免疫相关疾病、皮肤疾病、髓增生性疾病、癌症和其他疾病。
• Mild and highly efficient metal-free oxidative α-cyanation of N-acyl/sulfonyl tetrahydroisoquinolines
  作者：Changcun Yan、Yuxiu Liu、Qingmin Wang

  DOI：10.1039/c4ra12922a

  日期：——

  A highly efficient metal-free oxidative α-cyanation reaction of N-acyl/sulfonyl tetrahydroisoquinolines under mild conditions was developed. The reaction uses 2,2,6,6-tetramethylpiperidine N-oxide fluoroborate salt (T+BF4−) as the oxidant and trimethylsilyl cyanide as the source of the cyano group.

  研究人员开发了一种温和条件下 N-酰基/磺酰基四氢异喹啉的高效无金属氧化δ-氰化反应。该反应以 2,2,6,6-四甲基哌啶 N-氧化物氟硼酸盐 (T+BF4â) 为氧化剂，以三甲基硅氰作为氰基来源。