(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetonitrile | 199988-77-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetonitrile
• 英文别名: 2-(3,5,5,8,8-Pentamethyl-6,7-dihydronaphthalen-2-yl)acetonitrile
• CAS: 199988-77-7
• 化学式: C₁₇H₂₃N
• 分子量: 241.376
• InChiKey: CZTMFWGUHQMQKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetonitrile 在 氢氧化钾 、 正丁基锂 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2E,4E)-3-Methyl-5-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-cyclopentyl]-penta-2,4-dienoic acid
  参考文献：
  名称：

  Synthesis and structure-activity relationships of potent conformationally restricted retinoid X receptor ligands

  摘要：

  A series of potent retinoid X receptor (RXR) selective ligands were designed and prepared. The lead compound 6a, showed good binding (K-d; 3-7 nM) and transactivation (EC50; 19-24 nM) to the RXR subfamily of retinoid receptors. More importantly, a small variation on the aromatic ring moiety led to 6b, which had less residual RAR agonist activity with RXR binding and potency of 4-5 nM and 5-13 nM, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10079-8
• 作为产物：
  描述：

  乙腈 、 6-bromomethyl-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene 在 四乙基溴化铵 作用下， 以78%的产率得到(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetonitrile
  参考文献：
  名称：

  Synthesis and structure-activity relationships of potent conformationally restricted retinoid X receptor ligands

  摘要：

  A series of potent retinoid X receptor (RXR) selective ligands were designed and prepared. The lead compound 6a, showed good binding (K-d; 3-7 nM) and transactivation (EC50; 19-24 nM) to the RXR subfamily of retinoid receptors. More importantly, a small variation on the aromatic ring moiety led to 6b, which had less residual RAR agonist activity with RXR binding and potency of 4-5 nM and 5-13 nM, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10079-8

文献信息

• Synthesis and structure-activity relationships of potent conformationally restricted retinoid X receptor ligands
  作者：Luc J. Farmer、Lin Zhi、Susan Jeong、E. Adam Kallel、Glenn Croston、Karen S. Flatten、Rich A. Heyman、Alex M. Nadzan

  DOI：10.1016/s0960-894x(97)10079-8

  日期：1997.11

  A series of potent retinoid X receptor (RXR) selective ligands were designed and prepared. The lead compound 6a, showed good binding (K-d; 3-7 nM) and transactivation (EC50; 19-24 nM) to the RXR subfamily of retinoid receptors. More importantly, a small variation on the aromatic ring moiety led to 6b, which had less residual RAR agonist activity with RXR binding and potency of 4-5 nM and 5-13 nM, respectively. (C) 1997 Elsevier Science Ltd.