1,1,4,4-Tetramethyl-6-[(Z)-2-(4-nitro-phenyl)-vinyl]-1,2,3,4-tetrahydro-naphthalene | 326493-42-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,1,4,4-Tetramethyl-6-[(Z)-2-(4-nitro-phenyl)-vinyl]-1,2,3,4-tetrahydro-naphthalene
• CAS: 326493-42-9
• 化学式: C₂₂H₂₅NO₂
• 分子量: 335.446
• InChiKey: NLBQPLSEWJZOPO-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.11
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  43.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,1,4,4-Tetramethyl-6-[(Z)-2-(4-nitro-phenyl)-vinyl]-1,2,3,4-tetrahydro-naphthalene 在 溶剂黄146 、 锌 作用下， 生成 4-[(Z)-2-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-phenylamine
  参考文献：
  名称：

  Programmed cell death (PCD) associated with the stilbene motif of arotinoids: discovery of novel apoptosis inducer agents possessing activity on multidrug resistant tumor cells

  摘要：

  Considering that the stereochemistry of the C9-C10 alkenyl portion of natural 9-cis-RA, as the one of the olefinic moiety of the previously described isoxazole retinoid 4, seems of particular importance for their apoptotic activity, we prepared a novel class of TTNPB analogues bearing both the cis or trans configuration of the alkenyl portion. The compounds were evaluated in vitro for their cytotoxic and apoptotic activities. We discovered that the cis-TTNPB 9c possesses apoptotic activity comparable with that of the retinoid 4. Moreover, the amino arotinoid 16c showed potent apoptotic activity in HL60 promyelocytic leukemia cells. Interestingly, 16c proved to be a particularly potent apoptosis-inducing agent active in multidrug resistant (MDR) cell lines. Therefore, to the best of our knowledge, 16c may represent the first known aminoarotinoid endowed with potent apoptotic activity in MDR cells. Taken together, these results seem to point out that the cis-stilbene motif of arotinoids may be at least an important feature in conferring cytotoxic and apoptotic activity to this class of compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00547-3
• 作为产物：
  描述：

  对硝基苯甲醛 、 Bromo-triphenyl-[(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)methyl]-lambda5-phosphane 在 1,5,7-三氮杂双环[4.4.0]癸-5-烯 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 1,1,4,4-Tetramethyl-6-[(Z)-2-(4-nitro-phenyl)-vinyl]-1,2,3,4-tetrahydro-naphthalene 、 1,1,4,4-Tetramethyl-6-[(E)-2-(4-nitro-phenyl)-vinyl]-1,2,3,4-tetrahydro-naphthalene
  参考文献：
  名称：

  Strong Bicyclic Guanidine Base-Promoted Wittig and Horner−Wadsworth−Emmons Reactions

  摘要：

  [GRAPHICS]A convenient procedure to effect the Wittig and Horner-Wadsworth-Emmons reactions employs guanidine TBD and MTBD as base-promoters; mild reaction conditions, high efficiency, and facile isolation of the final products make the present methodology, at least in some cases, a practical alternative to known procedures.

  DOI：

  10.1021/ol0001665