1-乙酰基-4-碘萘 | 91493-16-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-乙酰基-4-碘萘
• 英文名称: 1-acetyl-4-iodonaphthalene
• 英文别名: 4-iodo-1-acetonaphtone；4-Iod-1-aceto-naphthon；1-(4-Iodonaphthalen-1-yl)ethanone
• CAS: 91493-16-2
• 化学式: C₁₂H₉IO
• 分子量: 296.107
• InChiKey: MLVGDKVJDNKSGA-UHFFFAOYSA-N

物化性质

• 熔点：
  72-73 °C(Solv: ethanol (64-17-5))
• 沸点：
  386.8±25.0 °C(Predicted)
• 密度：
  1.671±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-乙酰基-4-碘萘 在 水 、 碘 、 sodium hydroxide 作用下， 反应 2.67h， 生成 4-碘萘-1-羧酸
  参考文献：
  名称：

  Synthesis and pharmacology of 1-alkyl-3-(1-naphthoyl)indoles: Steric and electronic effects of 4- and 8-halogenated naphthoyl substituents

  摘要：

  To develop SAR at both the cannabinoid CB1 and CB2 receptors for 3-(1-naphthoyl)indoles bearing moderately electron withdrawing substituents at C-4 of the naphthoyl moiety, 1-propyl and 1-pentyl-3-(4-fluoro, chloro, bromo and iodo-1-naphthoyl) derivatives were prepared. To study the steric and electronic effects of substituents at the 8-position of the naphthoyl group, the 3-(4-chloro, bromo and iodo-1-naphthoyl) indoles were also synthesized. The affinities of both groups of compounds for the CB1 and CB2 receptors were determined and several of them were evaluated in vivo in the mouse. The effects of these substituents on receptor affinities and in vivo activity are discussed and structure-activity relationships are presented. Although many of these compounds are selective for the CB2 receptor, only three JWH-423, 1-propyl-3-(4-iodo-1-naphthoyl)indole, JWH-422, 2-methyl-1-propyl-3-(4-iodo-1-naphthoyl) indole, the 2-methyl analog of JWH-423 and JWH-417, 1-pentyl-3-(8-iodo-1-naphthoyl)indole, possess the desirable combination of low CB1 affinity and good CB2 affinity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.038
• 作为产物：
  描述：

  1-碘萘 、 乙酰氯 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 120.17h， 以55%的产率得到1-乙酰基-4-碘萘
  参考文献：
  名称：

  Synthesis and pharmacology of 1-alkyl-3-(1-naphthoyl)indoles: Steric and electronic effects of 4- and 8-halogenated naphthoyl substituents

  摘要：

  To develop SAR at both the cannabinoid CB1 and CB2 receptors for 3-(1-naphthoyl)indoles bearing moderately electron withdrawing substituents at C-4 of the naphthoyl moiety, 1-propyl and 1-pentyl-3-(4-fluoro, chloro, bromo and iodo-1-naphthoyl) derivatives were prepared. To study the steric and electronic effects of substituents at the 8-position of the naphthoyl group, the 3-(4-chloro, bromo and iodo-1-naphthoyl) indoles were also synthesized. The affinities of both groups of compounds for the CB1 and CB2 receptors were determined and several of them were evaluated in vivo in the mouse. The effects of these substituents on receptor affinities and in vivo activity are discussed and structure-activity relationships are presented. Although many of these compounds are selective for the CB2 receptor, only three JWH-423, 1-propyl-3-(4-iodo-1-naphthoyl)indole, JWH-422, 2-methyl-1-propyl-3-(4-iodo-1-naphthoyl) indole, the 2-methyl analog of JWH-423 and JWH-417, 1-pentyl-3-(8-iodo-1-naphthoyl)indole, possess the desirable combination of low CB1 affinity and good CB2 affinity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.038

文献信息

• Allosteric adenosine receptor modulators
  申请人：——

  公开号：US20010047008A1

  公开（公告）日：2001-11-29

  The present invention relates to compounds of formulas (IA) and (IB): 1 the preparation thereof, pharmaceutical formulations thereof, and their use in medicine as allosteric adenosine receptor modulators for uses including protection against hypoxia and ischemia induced injury and treatment of adenosine-sensitive cardiac arrhythmias.

  本发明涉及以下化合物的公式（IA）和（IB）：其制备、药物配方以及在医学中作为变构腺苷受体调节剂的用途，包括保护免受缺氧和缺血引起的损伤以及治疗对腺苷敏感的心律失常。
• Rajasekaran, Kasi; Gnanasekaran, Chinnasamy, Journal of the Chemical Society. Perkin transactions II, 1987, p. 263 - 266
  作者：Rajasekaran, Kasi、Gnanasekaran, Chinnasamy

  DOI：——

  日期：——
• RAJASEKARAN KASI; GNANASEKARAN CHINNASAMY, J. CHEM. SOC. PERKIN TRANS.,(1987) N 3, 263-266
  作者：RAJASEKARAN KASI、 GNANASEKARAN CHINNASAMY

  DOI：——

  日期：——
• EP1401441A4
  申请人：——

  公开号：EP1401441A4

  公开（公告）日：2006-09-06
• ALLOSTERIC ADENOSINE RECEPTOR MODULATORS
  申请人：King Pharmaceuticals Research and Development Inc.

  公开号：EP1401441A2

  公开（公告）日：2004-03-31