6-t-butyl-1,1-dimethyl-indan-4-ol triflate | 252556-30-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 6-t-butyl-1,1-dimethyl-indan-4-ol triflate
• 英文别名: Trifluoromethanesulfonic acid 1,1-dimethyl-6-tert-butyl-4-indanyl ester；(6-tert-butyl-1,1-dimethyl-2,3-dihydroinden-4-yl) trifluoromethanesulfonate
• CAS: 252556-30-2
• 化学式: C₁₆H₂₁F₃O₃S
• 分子量: 350.402
• InChiKey: OXZYLLNMYHCLLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-t-butyl-1,1-dimethyl-indan-4-ol triflate 在 N-甲基吲哚酮 、 四丙基高钌酸铵 、 tris(dibenzylideneacetone)dipalladium (0) 、 三苯胂 、 lithium chloride 作用下， 以 N-甲基吡咯烷酮 、 二氯甲烷 为溶剂， 生成 (2Z,4E)-5-(6-tert-Butyl-1,1-dimethyl-indan-4-yl)-3-methyl-penta-2,4-dienal
  参考文献：
  名称：

  9-cis-Retinoic acid analogues with bulky hydrophobic rings: new RXR-selective agonists

  摘要：

  Stille cross-coupling of aryltriflates 10 and dienylstannane 11, oxidation and Horner-Wadsworth-Emmons reaction afforded stereoselectively retinoates 15. Saponification provided the carboxylic acids 8a and 86, retinoids that incorporate a bulky hydrophobic ring while preserving the 9-cis-geometry of the parent system. In contrast to the pan-RAR/RXR agonistic profile of the lower homologue of 8a, compound 7 (LG100567), retinoids 8 showed selective binding and transactivation of RXR, devoid of significant RAR activation. In PLB985 leukemia cells that require RXR agonists for differentiation compounds 8 induced maturation in the presence of the RAR-selective pan-agonist TTNPB; this effect was blocked by an RXR-selective antagonist. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.072
• 作为产物：
  描述：

  N-苯基双(三氟甲烷磺酰)亚胺 、 6-tert-butyl-1,1-dimethylindanol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以98%的产率得到6-t-butyl-1,1-dimethyl-indan-4-ol triflate
  参考文献：
  名称：

  9-cis-Retinoic acid analogues with bulky hydrophobic rings: new RXR-selective agonists

  摘要：

  Stille cross-coupling of aryltriflates 10 and dienylstannane 11, oxidation and Horner-Wadsworth-Emmons reaction afforded stereoselectively retinoates 15. Saponification provided the carboxylic acids 8a and 86, retinoids that incorporate a bulky hydrophobic ring while preserving the 9-cis-geometry of the parent system. In contrast to the pan-RAR/RXR agonistic profile of the lower homologue of 8a, compound 7 (LG100567), retinoids 8 showed selective binding and transactivation of RXR, devoid of significant RAR activation. In PLB985 leukemia cells that require RXR agonists for differentiation compounds 8 induced maturation in the presence of the RAR-selective pan-agonist TTNPB; this effect was blocked by an RXR-selective antagonist. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.072

文献信息

• Retinoic acid receptor ligands based on the 6-cyclopropyl-2,4-hexadienoic acid
  作者：Luc J. Farmer、Lin Zhi、Susan Jeong、William W. Lamph、Deborah L. Osburn、Glenn Croston、Karen S. Flatten、Rich A. Heyman、Alex M. Nadzan

  DOI：10.1016/s0960-894x(02)00924-1

  日期：2003.1

  A series of novel cyclopropanyl methyl hexadienoic acid retinoids was designed and prepared. These compounds exhibited either selective activity as RXR agonists or pan-agonists on one or more of each of the RAR and RXR isoforms. The most potent pan-agonist 5a (RAR's EC50 = 17-59 nM; RXR's EC50 6-14 nM) showed good antiproliferative properties in the in vitro cancer cell lines, ME 180 and RPMI 8226. (C) 2002 Elsevier Science Ltd. All rights reserved.
• US6005007A
  申请人：——

  公开号：US6005007A

  公开（公告）日：1999-12-21
• [EN] NOVEL RETINOIDS, METHODS FOR THEIR PRODUCTION AND USE<br/>[FR] NOUVEAUX RETINOIDES ET TECHNIQUES DE LEUR PRODUCTION ET UTILISATION
  申请人：LIGAND PHARM INC

  公开号：WO2000026173A1

  公开（公告）日：2000-05-11

  Dienoic retinoids having activity for retinoid X receptors or being panagonists on retinoic acid receptors and retinoid X receptors are provided. Also provided are pharmaceutical compositions incorporating such compounds and methods for their therapeutic use.