5-chloro-1-(4-chlorophenyl)indane | 858224-85-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5-chloro-1-(4-chlorophenyl)indane
• 英文别名: 5-chloro-1-(4-chloro-phenyl)-indan；5-Chlor-1-(4-chlor-phenyl)-indan；5-chloro-1-(4-chlorophenyl)-2,3-dihydro-1H-indene
• CAS: 858224-85-8
• 化学式: C₁₅H₁₂Cl₂
• 分子量: 263.166
• InChiKey: JBXJOHNWFOFRRH-UHFFFAOYSA-N

物化性质

• 沸点：
  170-172 °C(Press: 3 Torr)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  5-chloro-1-(4-chlorophenyl)indane 在 盐酸 、 pseudomonas fluorescens lipase 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 水 、 二甲基亚砜 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 170.5h， 生成 (2R)-2-({3-[(S)-5-chloro-1-(4-chlorophenyl)indan-1-yl]propyl}methylamino)propionic acid
  参考文献：
  名称：

  Route Scouting and Process Development of Lu AA26778

  摘要：

  Route scouting and process development for the synthesis of (S)-2-({3-[(S)-5-chloro-1-(4-chloro-phenyl)indan-1-yl]propyl}methyl- amino)propionic acid, Lu AA26778, are described. The strategy is based on a short synthesis and SMB resolution of a key chiral intermediate for the introduction of one of the two stereocenters. The second stereocenter is introduced via a commercially available alanine ester, optionally bearing a N-methyl group. The main concern during scale-up of the synthesis was the safety of a step incorporating sodium dimsylate (the sodium salt of DMSO): this problem was solved using THF as a safety blanket in the large-scale process.

  DOI：

  10.1021/op7002584
• 作为产物：
  描述：

  6-chloro-3-(4-chlorophenyl)-2,3-dihydro-1H-inden-1-one 在 盐酸 、 amalgamated zinc 、 甲苯 作用下， 生成 5-chloro-1-(4-chlorophenyl)indane
  参考文献：
  名称：

  3-Phenylindones. I. The Synthesis of 6-Chloro-3-(p-chlorophenyl)-1-indenone and Some Related Compounds¹

  摘要：

  DOI：

  10.1021/ja01160a026

文献信息

• [EN] PHENYL INDAN DERIVATIVES<br/>[FR] DERIVES DE PHENYLE INDANE
  申请人：LUNDBECK & CO AS H

  公开号：WO2005087708A1

  公开（公告）日：2005-09-22

  This invention relates to novel compounds which are glycine transporter inhibitors and as such effective in the treatment of disorders in the CNS, such as schizophrenia.

  这项发明涉及一类新颖的化合物，这些化合物是甘氨酸转运蛋白抑制剂，因此对于治疗中枢神经系统疾病，如精神分裂症等，是有效的。
• PHENYL INDAN DERIVATIVES
  申请人：H.Lundbeck A/S

  公开号：EP1727785A1

  公开（公告）日：2006-12-06
• Route Scouting and Process Development of Lu AA26778
  作者：Allan C. Dahl、Michael J. Mealy、Martin A. Nielsen、Lars O. Lyngsø、Cristina Suteu

  DOI：10.1021/op7002584

  日期：2008.5.1

  Route scouting and process development for the synthesis of (S)-2-(3-[(S)-5-chloro-1-(4-chloro-phenyl)indan-1-yl]propyl}methyl- amino)propionic acid, Lu AA26778, are described. The strategy is based on a short synthesis and SMB resolution of a key chiral intermediate for the introduction of one of the two stereocenters. The second stereocenter is introduced via a commercially available alanine ester, optionally bearing a N-methyl group. The main concern during scale-up of the synthesis was the safety of a step incorporating sodium dimsylate (the sodium salt of DMSO): this problem was solved using THF as a safety blanket in the large-scale process.
• 3-Phenylindones. I. The Synthesis of 6-Chloro-3-(p-chlorophenyl)-1-indenone and Some Related Compounds¹
  作者：James F. Feeman、E. D. Amstutz

  DOI：10.1021/ja01160a026

  日期：1950.4