6-chloro-3-(4-chlorophenyl)-1H-indene | 1030603-31-6

• 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-3-(4-chlorophenyl)-1H-indene
• CAS: 1030603-31-6
• 化学式: C₁₅H₁₀Cl₂
• 分子量: 261.15
• InChiKey: BBCBTCFNOCRLSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  6-chloro-3-(4-chlorophenyl)-1H-indene 在 5%-palladium/activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 25.0 ℃ 、300.01 kPa 条件下， 反应 5.5h， 生成 5-chloro-1-(4-chlorophenyl)indane
  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：

  4,4'-(cycloprop-2-ene-1,1-diyl)bis(chlorobenzene) 在 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以96%的产率得到6-chloro-3-(4-chlorophenyl)-1H-indene
  参考文献：
  名称：

  在环境条件下，银催化酮的烯丙基化和通过环丙烯的碳中间体通过分子内环化

  摘要：

  串联C–C键的形成是通过卡宾中间体通过银催化的环丙烯的开环而实现的。环丙烯在银催化剂存在下的反应在环境条件下产生了茚衍生物。相反，将有机锌试剂插入到卡宾银或烯丙基阳离子中间体上可得到用于羰基化合物串联烯丙基化的烯丙基金属中间体。

  DOI：

  10.1002/asia.201501196

文献信息

• Silver-Catalyzed Allylation of Ketones and Intramolecular Cyclization through Carbene Intermediates from Cyclopropenes Under Ambient Conditions
  作者：Takeo Nakano、Kohei Endo、Yutaka Ukaji

  DOI：10.1002/asia.201501196

  日期：2016.3.4

  Tandem C−C bond formation was achieved through silver‐catalyzed ring‐opening of cyclopropenes via carbene intermediates. The reaction of cyclopropenes in the presence of a silver catalyst gave indene derivatives under ambient conditions. In contrast, the insertion of organozinc reagents to silver carbene or allylic cation intermediates afforded allylmetal intermediates for the tandem allylation of

  串联C–C键的形成是通过卡宾中间体通过银催化的环丙烯的开环而实现的。环丙烯在银催化剂存在下的反应在环境条件下产生了茚衍生物。相反，将有机锌试剂插入到卡宾银或烯丙基阳离子中间体上可得到用于羰基化合物串联烯丙基化的烯丙基金属中间体。
• 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.