6-fluoro-4-(methoxymethyl)-2,3-dihydro-1H-inden-1-one | 1092716-87-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 6-fluoro-4-(methoxymethyl)-2,3-dihydro-1H-inden-1-one
• 英文别名: 6-Fluoro-4-(methoxymethyl)-2,3-dihydroinden-1-one
• CAS: 1092716-87-4
• 化学式: C₁₁H₁₁FO₂
• 分子量: 194.206
• InChiKey: GMONYNXFUAMCPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-fluoro-4-(methoxymethyl)-2,3-dihydro-1H-inden-1-one 在 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 16.5h， 生成 6-fluoro-4-(methoxymethyl)-2,3-dihydro-1H-indene-1-carbonitrile
  参考文献：
  名称：

  A concise synthesis of chiral indanes as α 1A adrenoceptor partial agonists

  摘要：

  The synthesis of a series of chiral indanes with reported am partial agonist activity is outlined, applying a rhodium catalysed cyclisation for template construction. This method was extended to the asymmetric synthesis of lead compound PF-03774076 (1) which was prepared on >20 g scale in seven steps. Highlights include Rh-mediated cyclocarbonylation and an asymmetric alkene hydrogenation. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.004
• 作为产物：
  描述：

  2-碘-5-氟甲苯 在 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 三乙胺 、 三苯基膦 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 水 、 N,N-二甲基甲酰胺 为溶剂， 20.0~160.0 ℃ 、6.89 MPa 条件下， 反应 76.0h， 生成 6-fluoro-4-(methoxymethyl)-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  A concise synthesis of chiral indanes as α 1A adrenoceptor partial agonists

  摘要：

  The synthesis of a series of chiral indanes with reported am partial agonist activity is outlined, applying a rhodium catalysed cyclisation for template construction. This method was extended to the asymmetric synthesis of lead compound PF-03774076 (1) which was prepared on >20 g scale in seven steps. Highlights include Rh-mediated cyclocarbonylation and an asymmetric alkene hydrogenation. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.004

文献信息

• Novel 2-imidazoles as potent, selective and CNS penetrant α1A adrenoceptor partial agonists
  作者：Lee R. Roberts、Justin Bryans、Kelly Conlon、Gordon McMurray、Alan Stobie、Gavin A. Whitlock

  DOI：10.1016/j.bmcl.2008.10.066

  日期：2008.12

  A novel series of central nervous system (CNS) penetrant indane 2-imidazoles have been identified as potent, partial agonists of the alpha(1A) adrenergic receptor, having good selectivity over the alpha(1B), alpha(1D) and alpha(2) sub-types. A key structural motif to impart selectivity is a methylene spacer between the indane and a pendant substituent, which includes heterocycles, sulphones and ethers. Introduction of an ortho-halogen to this group led to a lowering of intrinsic efficacy (E-max). (C) 2008 Elsevier Ltd. All rights reserved.