2-phenylpropyl 4-methylbenzenesulfonate | 74669-73-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-phenylpropyl 4-methylbenzenesulfonate
• 英文别名: S-(-)-2-phenyl-1-(tosyloxy)propane；(S)-2-phenylpropyl tosylate；(S)-2-Phenylpropyltosylat；toluene-4-sulfonic acid (S)-2-phenyl-propyl ester；[(2S)-2-phenylpropyl] 4-methylbenzenesulfonate
• CAS: 74669-73-1
• 化学式: C₁₆H₁₈O₃S
• 分子量: 290.383
• InChiKey: LWODUZBQQRSKOF-CQSZACIVSA-N

物化性质

• 沸点：
  428.7±24.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-phenylpropyl 4-methylbenzenesulfonate 在 lithium aluminium tetrahydride 、 sodium azide 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 20.0h， 生成 (R)-2-苯基-1-丙胺
  参考文献：
  名称：

  Kirmse, Wolfgang; Guenther, Bernd-Rainer; Loosen, Karin, Chemische Berichte, 1980, vol. 113, # 6, p. 2140 - 2153

  摘要：

  DOI：
• 作为产物：
  描述：

  S-2-苯基丙酸 在 吡啶 、 红铝 作用下， 以 甲苯 为溶剂， 反应 2.5h， 生成 2-phenylpropyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  A short stereocontrolled synthesis of hydroxyethylene dipeptide isosteres

  摘要：

  A stereocontrolled synthesis of protected hydroxyethylene dipeptide isosteres 14 and 16 is described. It provides the 2R,4S,5S epimers required for the preparation of aspartic proteinase inhibitors. The choice of a benzene ring as a precursor to the carboxylic acid function has enabled us to use the readily accessible chiral Grignard reagent 3 which reacts with the protected alpha-amino aldehyde 8 stereoselectively. Kilogram quantities of 16 have been produced by this route in a satisfactory overall yield. The combination of N- and 0-protecting groups employed facilitates the incorporation of 14 or 16 into peptide-based enzyme inhibitors.

  DOI：

  10.1021/jo00060a052

文献信息

• [EN] ARYLSULFONYLMETHYL OR ARYLSULFONAMIDE SUBSTITUTED AROMATIC COMPOUNDS SUITABLE FOR TREATING DISORDERS THAT RESPOND TO MADULATION OF THE DOPAMINE D3 RECEPTOR<br/>[FR] COMPOSES AROMATIQUES D'ARYLSULFONYLMETHYLE OU D'ARYLSULFONAMIDE SUBSTITUES PERMETTANT DE TRAITER DES TROUBLES REPONDANT A UNE MODULATION DU RECEPTEUR D3 DE LA DOPAMINE
  申请人：ABBOTT GMBH & CO KG

  公开号：WO2006040178A1

  公开（公告）日：2006-04-20

  The present invention relates to aromatic compounds of the formula (I), wherein Ar is phenyl or an aromatic 5- or 6-membered C-bound heteroaromatic radical, wherein Ar may carry 1 radical Ra and wherein Ar may also carry 1 or 2 radicals Rb; X is N or CH; Y is O, S, -CH=N-, -CH=CH- or -N=CH-; A is CH2i O or S; E is CR6R7 or NR 3; R1 is C1-C4-alkyl, C3-C4-cycloalkyl, C3-C4-cycloalkylmethyl, C3-C4-alkenyl, fluorinated C1-C4-­alkyl, fluorinated C3-C4-cycloalkyl, fluorinated C3-C4-cycloalkylmethyl, fluorinated C3-C4­-alkenyl, formyl or C,-C3-alkylcarbonyl; R1a is H, C2-C4-alkyl, C3-C4-cycloalkyl, C3-C4-alkenyl, fluorinated C1-C4-alkyl, fluorinated C3-C4 -cycloalkyl, or R1a and R2 together are (CH2)n with n being 2 or 3, or R1a and R2a together are (CH2)n with n being 2 or 3; R2 and R2a are independently of each other H, CH3, CH2F, CHF2 or CF3; R3 is H or C1-C4-alkyl; R6, R7 independently of each other are selected from H, C1-C2-alkyl and fluorinated C1-C2-alkyl; and the physiologically tolerated acid addition salts thereof. The invention also relates to the use of a compound of the formula I or a pharmaceutically acceptable salt thereof for preparing a pharmaceutical composition for the treatment of a medical disorder susceptible to treatment with a dopamine D3 receptor ligand.

  本发明涉及式(I)的芳香族化合物，其中Ar是苯基或芳香族5-或6-成员C-键合杂芳基，其中Ar可以携带1个基团Ra，Ar也可以携带1个或2个基团Rb；X是N或CH；Y是O、S、-CH=N-、-CH=CH-或-N=CH-；A是CH2i、O或S；E是CR6R7或NR3；R1是C1-C4-烷基、C3-C4-环烷基、C3-C4-环烷基甲基、C3-C4-烯基、氟代C1-C4-烷基、氟代C3-C4-环烷基、氟代C3-C4-环烷基甲基、氟代C3-C4-烯基、甲酰基或C,-C3-烷基羰基；R1a是H、C2-C4-烷基、C3-C4-环烷基、C3-C4-烯基、氟代C1-C4-烷基、氟代C3-C4-环烷基，或R1a和R2一起是(CH2)n，其中n为2或3，或R1a和R2a一起是(CH2)n，其中n为2或3；R2和R2a彼此独立地是H、CH3、CH2F、CHF2或CF3；R3是H或C1-C4-烷基；R6、R7彼此独立地选自H、C1-C2-烷基和氟代C1-C2-烷基；以及其生理耐受的酸盐。该发明还涉及使用式I的化合物或其药学上可接受的盐制备用于治疗对多巴胺D3受体配体敏感的医疗疾病的药物组合物。
• S_N2 Type Hydrolysis of Secondary Alkyl Halides and Sulfonates in Hydrothermal Water
  作者：Yuki Yamasaki、Takaharu Hirayama、Koichiro Oshima、Seijiro Matsubara

  DOI：10.1246/cl.2004.864

  日期：2004.7

  Optically active secondary alkyl halides and sulfonates were treated with alkaline hydrothermal water at 250 °C in sealed vessel. The hydrolysis mostly proceeded with inversion of stereochemistry.

  光学活性的仲烷基卤化物和磺酸盐在密封容器中在 250°C 下用碱性热水处理。水解主要是通过立体化学的反转进行的。
• [EN] AMINOETHYLAROMATIC COMPOUNDS SUITABLE FOR TREATING DISORDERS THAT RESPOND TO MODULATION OF THE DOPAMINE D3 RECEPTOR<br/>[FR] COMPOSES AMINOETHYLAROMATIQUES PERMETTANT DE TRAITER DES TROUBLES REPONDANT A UNE MODULATION DU RECEPTEUR D3 DE LA DOPAMINE
  申请人：ABBOTT GMBH & CO KG

  公开号：WO2006040179A1

  公开（公告）日：2006-04-20

  The present invention relates to aromatic compounds of the formula (I) wherein Ar is phenyl or an aromatic 5- or 6-membered C-bound heteroaromatic radical, wherein Ar may carry 1 radical Ra and wherein Ar may also carry 1 or 2 radicals Rb; X is N or CH; E is CR6R7 or NR3; R1 is C1-C4-alkyl, C3-C4-cycloalkyl, C3-C4-cycloalkylmethyl, C3-C4-alkenyl, fluorinated Cl-C4­-alkyl, fluorinated C3-C4-cycloalkyl, fluorinated C3-C4-cycloalkylmethyl, fluorinated C3-C4­-alkenyl, formyl or C1-C3-alkylcarbonyl; R1a is H, C1-C4-alkyl, C3-C4-cycloalkyl, C3-C4-cycloalkylmethyl, C3-C4-alkenyl, fluorinated C1-­C4-alkyl, fluorinated C3-C4-cycloalkyl, fluorinated C3-C4-cycloalkylmethyl, fluorinated C3­-C4-alkenyl, or R1a and R2 together are (CH2)n with n being 2, 3 or 4, or R1a and R2a together are (CH2)n with n being 2, 3 or 4; R2 and R2a are independently of each other H, C1-C4-alkyl or fluorinated C1-C4-alkyl or R2a and R2 together are (CH2)m with m being 1, 2, 3, 4 or 5; R3 is H or C1-C4-alkyl; R6, R7 independently of each other are selected from H, fluorine, C1-C4-alkyl and fluorinated C1-C4-alkyl or together form a moiety (CH2)p with p being 2, 3, 4 or 5; and the physiologically tolerated acid addition salts thereof. The invention also relates to the use of a compound of the formula (I) or a pharmaceutically acceptable salt thereof for preparing a pharmaceutical composition for the treatment of a medical disorder susceptible to treatment with a dopamine D3 receptor ligand.

  本发明涉及公式（I）的芳香族化合物，其中Ar为苯基或芳香族5-或6-成员C-键合杂环基，其中Ar可能携带1个基团Ra，Ar也可能携带1个或2个基团Rb；X为N或CH；E为CR6R7或NR3；R1为C1-C4-烷基，C3-C4-环烷基，C3-C4-环烷基甲基，C3-C4-烯基，氟代的Cl-C4-烷基，氟代的C3-C4-环烷基，氟代的C3-C4-环烷基甲基，氟代的C3-C4-烯基，甲酰基或C1-C3-烷基羰基；R1a为H，C1-C4-烷基，C3-C4-环烷基，C3-C4-环烷基甲基，C3-C4-烯基，氟代的C1-C4-烷基，氟代的C3-C4-环烷基，氟代的C3-C4-环烷基甲基，氟代的C3-C4-烯基，或R1a和R2一起为（CH2）n，其中n为2、3或4，或R1a和R2a一起为（CH2）n，其中n为2、3或4；R2和R2a彼此独立为H，C1-C4-烷基或氟代的C1-C4-烷基，或R2a和R2一起为（CH2）m，其中m为1、2、3、4或5；R3为H或C1-C4-烷基；R6、R7彼此独立地选自H、氟、C1-C4-烷基和氟代的C1-C4-烷基，或一起形成一个(CH2)p的基团，其中p为2、3、4或5；以及其生理耐受的酸盐。该发明还涉及使用公式（I）的化合物或其药学上可接受的盐来制备用于治疗可用多巴胺D3受体配体治疗的医疗疾病的药物组合物。
• [EN] HETEROCYCLIC COMPOUNDS SUITABLE FOR TREATING DISORDERS THAT RESPOND TO MODULATION OF THE DOPAMINE D3 RECEPTOR<br/>[FR] COMPOSES HETEROCYCLIQUES CONVENANT POUR TRAITER DES TROUBLES SENSIBLES A UNE MODULATION DU RECEPTEUR D3 DE LA DOPAMINE
  申请人：ABBOTT GMBH & CO KG

  公开号：WO2006040182A1

  公开（公告）日：2006-04-20

  The invention relates to compounds of the formula (I) wherein n is 0, 1 or 2; G is CH2 or CHR3; R1 is H, C,-C6-alkyl, C,-C6-alkyl substituted by C3-C6-cycloalkyl, Cl-C6-hydroxyalkyl, fluorinated C,-C6-alkyl, C3-C6-cycloalkyl, fluorinated C3-C6-cycloalkyl, C3-C6­ alkenyl, fluorinated C3-C6-alkenyl, formyl, acetyl or propionyl; R2, R3 and R4 are, independently of each other, H, methyl, fluoromethyl, difluoromethyl, or trifluoromethyl; A is phenylene, pyridylene, pyrimidylene, pyrazinylene, pyridazinylene or thiophenylene, which can be substituted by one ore more substituents selected from halogen, methyl, methoxy and CF3; E is NR5 or CH2, wherein R5 is H or C1 -C3-alkyl; Ar is a cyclic radical selected from the group consisting of phenyl, a 5- or 6- ­membered heteroaromatic radical comprising as ring members 1, 2 or 3 heteroatoms selected from N, O and S and a phenyl ring fused to a saturated or unsaturated 5- or 6-membered carbocyclic or heterocyclic ring, where the heterocyclic ring comprises as ring members 1, 2 or 3 heteroatoms selected from N, O and S and/or 1, 2 or 3 heteroatom-containing groups each independently selected from NR8, where R8 is H, C1-C4-alkyl, fluorinated C1-C4-alkyl, C1-C4­alkylcarbonyl or fluorinated C1-C4-alkylcarbonyl, and where the cyclic radical Ar may carry 1, 2 or 3 substituents Ra, wherein the variable Ra has the meanings given in the claims and in the description; and physiologically tolerated acid addition salts thereof. The invention also relates to the use of a compound of the formula I or a pharmaceutically acceptable salt thereof for preparing a pharmaceutical composition for the treatment of a medical disorder susceptible to treatment with a dopamine D3 receptor ligand.

  该发明涉及以下式(I)的化合物，其中n为0、1或2；G为CH2或CHR3；R1为H、C1-C6烷基、被C3-C6环烷基取代的C1-C6烷基、Cl-C6羟基烷基、氟化的C1-C6烷基、C3-C6环烷基、氟化的C3-C6环烷基、C3-C6烯基、氟化的C3-C6烯基、甲酰基、乙酰基或丙酰基；R2、R3和R4独立地为H、甲基、氟甲基、二氟甲基或三氟甲基；A为苯基、吡啶基、嘧啶基、吡嗪基、吡啶嗪基或噻吩基，可以被卤素、甲基、甲氧基和CF3等一个或多个取代基取代；E为NR5或CH2，其中R5为H或C1-C3烷基；Ar为从苯基、含有1、2或3个异原子N、O和S的5-或6-元杂环芳基、以及与饱和或不饱和的5-或6-元碳环或杂环融合的苯基环组成的环状基，其中杂环环包含1、2或3个异原子N、O和S和/或1、2或3个异原子含氮基团，每个基团独立地选择自NR8，其中R8为H、C1-C4烷基、氟化的C1-C4烷基、C1-C4烷基酰基或氟化的C1-C4烷基酰基，环状基Ar可以携带1、2或3个取代基Ra，其中变量Ra具有权利要求和描述中给出的含义；以及其生理上可耐受的酸盐。该发明还涉及使用式I的化合物或其药学上可接受的盐制备用于治疗易受多巴胺D3受体配体治疗的医疗紊乱的药物组合物。
• [EN] AMINOMETHYL SUBSTITUTED BICYCLIC AROMATIC COMPOUNDS SUITABLE FOR TREATING DISORDERS THAT RESPOND TO MODULATION OF THE DOPAMINE D3 RECEPTOR<br/>[FR] COMPOSES AROMATIQUES BICYCLIQUES AMINOMETHYLE SUBSTITUES PERMETTANT DE TRAITER DES TROUBLES REPONDANT A UNE MODULATION DU RECEPTEUR D3 DE LA DOPAMINE
  申请人：ABBOTT GMBH & CO KG

  公开号：WO2006040180A1

  公开（公告）日：2006-04-20

  The present invention relates to an aminomethyl substituted bicyclic aromatic compound of the formula (I) wherein Ar is a cyclic radical selected from the group consisting of phenyl, a 5- or 6-membered C-bound heteroaromatic radical comprising as ring member 1, 2 or 3 heteroatoms which are, independently of each other, selected from O, S and N, and a phenyl ring fused to a saturated or unsaturated 5- or 6-membered carbocyclic or heterocyclic ring, where the heterocyclic ring comprises as ring members 1, 2 or 3 heteroatoms selected from N, O and S and/or 1, 2 or 3 heteroatom-containing groups each independently selected from NR8, where R8 is H, C1-C4-alkyl, fluorinated C1-C4-alkyl, C1-C4-alkylcarbonyl or fluorinated C1-C4-alkylcarbonyl, and where the cyclic radical Ar may carry 1, 2 or 3 substituents Ra, wherein the variable Ra has the meanings given in the claims and in the description; X is a covalent bond or N-R2, CHR2, CHR2CH2, N or C-R2; Y is N-R2a, CHR2a, CHR2aCH2 or CHR2aCH2CH2; is a single bond or a double bond; E is CH2 or NR3; R1 is H, C1-C4-alkyl, C3-C4-cycloalkyl, C3-C4-cycloalkylmethyl, C3-C4-alkenyl, fluorinated C1­-C4-alkyl, fluorinated C3-C4-cycloalkyl, fluorinated C3-C4-cycloalkylmethyl, fluorinated C3­-C4-alkenyl, formyl or C1-C3-alkylcarbonyl; R1a is H, C1-C4-alkyl, C3-C4-cycloalkyl, C3-C4-alkenyl, fluorinated C1-C4-alkyl, fluorinated C3­-C4-cycloalkyl, fluorinated C3-C4-alkenyl, R2 and R2a each independently are H, CH3, CH2F, CHF2 or CF3 or R1a and R2 or R1a and R2a together are (CH2)n with n being 1, 2 or 3; R3 is H or C1-C4-alkyl; R4 and R5 independently of each other are H, C1-C4-alkyl, fluorinated C1-C4-alkyl or C1-C4­-alkoxy or may form, together with N, a 4-, 5- or 6-membered saturated or unsaturated ring; R6 and R7 independently of each other are H or halogen; and the physiologically tolerated acid addition salts thereof. The invention also relates to the use of a compound of the formula (I) or a pharmaceutically acceptable salt thereof for preparing a pharmaceutical composition for the treatment of a medical disorder susceptible to treatment with a dopamine D3 receptor ligand.

  本发明涉及一种氨甲基取代的双环芳香化合物，其化学式为(I)，其中Ar是从苯基、一个含有1、2或3个杂原子的5-或6成员C-键合杂芳基组成的环状基团中选择的循环基团，这些杂原子独立地选择自O、S和N，以及与饱和或不饱和的5-或6成员碳环或杂环融合的苯环，其中杂环包括作为环成员的1、2或3个选自N、O和S的杂原子和/或每个独立选择自NR8的1、2或3个含杂原子的基团，其中R8为H、C1-C4-烷基、氟代C1-C4-烷基、C1-C4-烷基酰基或氟代C1-C4-烷基酰基，环状基团Ar可能携带1、2或3个取代基Ra，其中变量Ra具有权利要求和描述中给定的含义；X是共价键或N-R2、CHR2、CHR2CH2、N或C-R2；Y是N-R2a、CHR2a、CHR2aCH2或CHR2aCH2CH2；是单键或双键；E是CH2或NR3；R1是H、C1-C4-烷基、C3-C4-环烷基、C3-C4-环烷基甲基、C3-C4-烯基、氟代C1-C4-烷基、氟代C3-C4-环烷基、氟代C3-C4-环烷基甲基、氟代C3-C4-烯基、甲酰基或C1-C3-烷基酰基；R1a是H、C1-C4-烷基、C3-C4-环烷基、C3-C4-烯基、氟代C1-C4-烷基、氟代C3-C4-环烷基、氟代C3-C4-烯基，R2和R2a各自独立地为H、CH3、CH2F、CHF2或CF3，或者R1a和R2或R1a和R2a一起为(CH2)n，其中n为1、2或3；R3为H或C1-C4-烷基；R4和R5独立地为H、C1-C4-烷基、氟代C1-C4-烷基或C1-C4-烷氧基，或者与N一起形成4、5或6成员饱和或不饱和环；R6和R7独立地为H或卤素；以及其生理耐受的酸盐加合物。该发明还涉及使用化合物(I)或其药学上可接受的盐制备用于治疗对多巴胺D3受体配体治疗敏感的医疗紊乱的药物组合物。