6-chloro-5-methoxy-1-phenyl-1H-indene | 475654-44-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 6-chloro-5-methoxy-1-phenyl-1H-indene
• 英文别名: 5-Chloro-6-methoxy-3-phenyl-1H-indene；5-chloro-6-methoxy-3-phenyl-1H-indene
• CAS: 475654-44-5
• 化学式: C₁₆H₁₃ClO
• 分子量: 256.732
• InChiKey: YWJWGPJEMXRRDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  6-chloro-5-methoxy-1-phenyl-1H-indene 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二乙二醇二甲醚 、 丙酮 为溶剂， 反应 39.0h， 生成 trans-N-methyl-N-n-propyl-2-amino-6-chloro-5-methoxy-1-phenyl-2,3-dihydro-1H-indene
  参考文献：
  名称：

  Synthesis and preliminary pharmacological evaluation of trans-2-amino-5(6)-chloro-6(5)-hydroxy-1-phenyl-2,3-dihydro-1H-indenes as dopamine receptor ligands

  摘要：

  A series of trans-2-amino-5(6)-chloro-6(5)-hydroxy-1-phenyl-2,3-dihydro-1H-indenes were synthesized and evaluated for their binding affinity toward D-1-like and D-2-like dopamine (DA) receptors. The affinity and selectivity of these compounds were measured in a test involving displacement of [H-3]SCH 23390 or [H-3]YM-09-151-2, respectively, from homogenates of porcine striatal membranes. All tested compounds were poorly effective at DA receptors (K-i nM > 1000). The results suggest that introduction of chlorine substituent in five or six position of previously synthesized trans-2-amino-6(5)-hydroxy-1-phenyl-2,3-dihydro-1H-indenes decreases both D-1-like and D-2-like receptor affinity. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01206-5
• 作为产物：
  描述：

  3-(4-chloro-3-methoxy)phenyl-propanoic acid 在 三氯化铝 、 氯化亚砜 、 碘 、 magnesium 作用下， 以 二硫化碳 、 乙醚 为溶剂， 反应 4.67h， 生成 6-chloro-5-methoxy-1-phenyl-1H-indene
  参考文献：
  名称：

  Synthesis and preliminary pharmacological evaluation of trans-2-amino-5(6)-chloro-6(5)-hydroxy-1-phenyl-2,3-dihydro-1H-indenes as dopamine receptor ligands

  摘要：

  A series of trans-2-amino-5(6)-chloro-6(5)-hydroxy-1-phenyl-2,3-dihydro-1H-indenes were synthesized and evaluated for their binding affinity toward D-1-like and D-2-like dopamine (DA) receptors. The affinity and selectivity of these compounds were measured in a test involving displacement of [H-3]SCH 23390 or [H-3]YM-09-151-2, respectively, from homogenates of porcine striatal membranes. All tested compounds were poorly effective at DA receptors (K-i nM > 1000). The results suggest that introduction of chlorine substituent in five or six position of previously synthesized trans-2-amino-6(5)-hydroxy-1-phenyl-2,3-dihydro-1H-indenes decreases both D-1-like and D-2-like receptor affinity. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01206-5