(R)-(-)-2,5-dimethoxy-4-(1-methylpropyl)benzaldehyde | 166446-88-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (R)-(-)-2,5-dimethoxy-4-(1-methylpropyl)benzaldehyde
• 英文别名: 4-[(2R)-butan-2-yl]-2,5-dimethoxybenzaldehyde
• CAS: 166446-88-4
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: WHITVDMDFRMBIU-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(-)-2,5-dimethoxy-4-(1-methylpropyl)benzaldehyde 在 lithium aluminium tetrahydride 、 ammonium acetate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.5h， 生成 2-[4-((R)-sec-Butyl)-2,5-dimethoxy-phenyl]-1-methyl-ethylamine
  参考文献：
  名称：

  Effect of a Chiral 4-Alkyl Substituent in Hallucinogenic Amphetamines

  摘要：

  The potency of hallucinogenic amphetamine derivatives of the 1-(2,5-dimethoxy-4-alkylphenyl)-2-aminopropane type drops dramatically when the length of the 4-alkyl substituent exceeds propyl or when the substituent is branched. This investigation was directed toward evaluating changes in behavioral and biochemical pharmacology resulting from introducing chirality into the 4-alkyl group of such analogues. Two diastereoisomeric derivatives of this class containing a 4-(R or S)-2-butyl substituent, 11a,b,respectively, were studied. A slight but nonsignificant potency difference in d-lysergic acid diethylamide tartrate (LSD)-like discriminative stimulus properties and equal affinity for [I-125]-(R)-(2,5-dimethoxy-4-iodophenyl)isopropylamine-labeled serotonin 5-HT2A/C radioligand-binding sites were observed. Thus, the portion of the receptor that interacts with the 4-alkyl substituent on hallucinogenic amphetamines does not present a highly asymmetric environment to the ligand. However, since both test drugs had higher binding affinity but lower LSD-like behavioral potency than the prototype compound with a 4-methyl group ((2, 5-dimethoxy-4-methylphenyl)isopropylamine, 2), 11a,b may differ in their receptor agonist efficacy from more behaviorally active compounds such as 2.

  DOI：

  10.1021/jm00018a019
• 作为产物：
  描述：

  2,5-二甲氧基苯乙酮 在 吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 正丁基锂 、 (+)-monoisopinocampheylborane 、 双氧水 、 四氯化锡 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 氯仿 为溶剂， 反应 127.5h， 生成 (R)-(-)-2,5-dimethoxy-4-(1-methylpropyl)benzaldehyde
  参考文献：
  名称：

  Effect of a Chiral 4-Alkyl Substituent in Hallucinogenic Amphetamines

  摘要：

  The potency of hallucinogenic amphetamine derivatives of the 1-(2,5-dimethoxy-4-alkylphenyl)-2-aminopropane type drops dramatically when the length of the 4-alkyl substituent exceeds propyl or when the substituent is branched. This investigation was directed toward evaluating changes in behavioral and biochemical pharmacology resulting from introducing chirality into the 4-alkyl group of such analogues. Two diastereoisomeric derivatives of this class containing a 4-(R or S)-2-butyl substituent, 11a,b,respectively, were studied. A slight but nonsignificant potency difference in d-lysergic acid diethylamide tartrate (LSD)-like discriminative stimulus properties and equal affinity for [I-125]-(R)-(2,5-dimethoxy-4-iodophenyl)isopropylamine-labeled serotonin 5-HT2A/C radioligand-binding sites were observed. Thus, the portion of the receptor that interacts with the 4-alkyl substituent on hallucinogenic amphetamines does not present a highly asymmetric environment to the ligand. However, since both test drugs had higher binding affinity but lower LSD-like behavioral potency than the prototype compound with a 4-methyl group ((2, 5-dimethoxy-4-methylphenyl)isopropylamine, 2), 11a,b may differ in their receptor agonist efficacy from more behaviorally active compounds such as 2.

  DOI：

  10.1021/jm00018a019

文献信息

• Effect of a Chiral 4-Alkyl Substituent in Hallucinogenic Amphetamines
  作者：Robert Oberlender、P. V. Ramachandran、Michael P. Johnson、Xuemei Huang、David E. Nichols

  DOI：10.1021/jm00018a019

  日期：1995.9

  The potency of hallucinogenic amphetamine derivatives of the 1-(2,5-dimethoxy-4-alkylphenyl)-2-aminopropane type drops dramatically when the length of the 4-alkyl substituent exceeds propyl or when the substituent is branched. This investigation was directed toward evaluating changes in behavioral and biochemical pharmacology resulting from introducing chirality into the 4-alkyl group of such analogues. Two diastereoisomeric derivatives of this class containing a 4-(R or S)-2-butyl substituent, 11a,b,respectively, were studied. A slight but nonsignificant potency difference in d-lysergic acid diethylamide tartrate (LSD)-like discriminative stimulus properties and equal affinity for [I-125]-(R)-(2,5-dimethoxy-4-iodophenyl)isopropylamine-labeled serotonin 5-HT2A/C radioligand-binding sites were observed. Thus, the portion of the receptor that interacts with the 4-alkyl substituent on hallucinogenic amphetamines does not present a highly asymmetric environment to the ligand. However, since both test drugs had higher binding affinity but lower LSD-like behavioral potency than the prototype compound with a 4-methyl group ((2, 5-dimethoxy-4-methylphenyl)isopropylamine, 2), 11a,b may differ in their receptor agonist efficacy from more behaviorally active compounds such as 2.