(2E,6E)-2,6-bis(p-nitrobenzylidene)-4-tert-butylcyclohexanone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (2E,6E)-2,6-bis(p-nitrobenzylidene)-4-tert-butylcyclohexanone
• 英文别名: (2E,6E)-4-tert-butyl-2,6-bis[(4-nitrophenyl)methylidene]cyclohexan-1-one
• 化学式: C₂₄H₂₄N₂O₅
• 分子量: 420.465
• InChiKey: JSJGJOXQLRDQFF-KLCVKJMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-丁二烯酸乙酯 、 (2E,6E)-2,6-bis(p-nitrobenzylidene)-4-tert-butylcyclohexanone 在 (S,S)-1,1'-bis(trimethylsilyl)-2,2'-(2-cyclohexyl-2-phospha-1,3-propanediyl)ferrocene 作用下， 以 甲苯 为溶剂， 反应 60.0h， 生成 、 、
  参考文献：
  名称：

  通过对映体膦催化的[3 + 2]环状杂环螺环和双螺环烷

  摘要：

  在膦催化下，烯丙酸酯和烯酮之间的[3 + 2]环化反应已完成了高度官能化的杂环螺烷的合成。在FerroPHANE促进的此类环化反应中，已达到出色的对映选择性水平（ee高达99％），从而导致了具有空前螺环结构的手性硫化物。然后通过随后的对酯基硫中心的高度非对映选择性氧化获得了相应的亚砜。

  DOI：

  10.1002/adsc.201100748
• 作为产物：
  描述：

  对硝基苯甲醛 、 4-叔丁基环己酮 在 盐酸 作用下， 反应 16.0h， 以68%的产率得到(2E,6E)-2,6-bis(p-nitrobenzylidene)-4-tert-butylcyclohexanone
  参考文献：
  名称：

  Cytotoxic analogues of 2,6-bis(arylidene)cyclohexanones

  摘要：

  A series of 2,6-bis(arylidene)cycloalkanones (1) and related compounds containing one or two substituents at the four position of the cyclohexyl ring were prepared and shown to display cytotoxic activity towards murine P388 and L1210 cells as ell as human Molt 4/C8 and CEM T-lymphoctes. In some of the series of compounds. positive e correlations were noted between the potencies of the enones and the magnitude of the Hammett c values of the aryl substituents. Four representatives compounds were cytotoxic to a number of human tumours in vitro. particularly towards colon cancer and leukemic cells. A noteworthy feature of the compounds prepared in this study is that. in general, they were well tolerated when administered to rodents. A number of lead molecules emerged from this investigation as well as guidelines for future expansion of these series of compounds. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01444-7

文献信息

• Cytotoxic analogues of 2,6-bis(arylidene)cyclohexanones
  作者：Jonathan R Dimmock、Maniyan P Padmanilayam、Gordon A Zello、Kurt H Nienaber、Theresa M Allen、Cheryl L Santos、Erik De Clercq、Jan Balzarini、Elias K Manavathu、James P Stables

  DOI：10.1016/s0223-5234(02)01444-7

  日期：2003.2

  A series of 2,6-bis(arylidene)cycloalkanones (1) and related compounds containing one or two substituents at the four position of the cyclohexyl ring were prepared and shown to display cytotoxic activity towards murine P388 and L1210 cells as ell as human Molt 4/C8 and CEM T-lymphoctes. In some of the series of compounds. positive e correlations were noted between the potencies of the enones and the magnitude of the Hammett c values of the aryl substituents. Four representatives compounds were cytotoxic to a number of human tumours in vitro. particularly towards colon cancer and leukemic cells. A noteworthy feature of the compounds prepared in this study is that. in general, they were well tolerated when administered to rodents. A number of lead molecules emerged from this investigation as well as guidelines for future expansion of these series of compounds. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• Heterocyclic Spiranes and Dispiranes via Enantioselective Phosphine-Catalyzed [3+2] Annulations
  作者：Deepti Duvvuru、Nathalie Pinto、Catherine Gomez、Jean-François Betzer、Pascal Retailleau、Arnaud Voituriez、Angela Marinetti

  DOI：10.1002/adsc.201100748

  日期：2012.2

  The synthesis of highly functionalized heterocyclic spiranes has been carried out by [3+2] cyclizations between allenoates and enones, under phosphine catalysis. Excellent enantioselectivity levels (ees up to 99%) have been attained in FerroPHANE-promoted cyclizations of this class, leading to chiral sulfides with unprecedented spiranic structures. The corresponding sulfoxides have been obtained then

  在膦催化下，烯丙酸酯和烯酮之间的[3 + 2]环化反应已完成了高度官能化的杂环螺烷的合成。在FerroPHANE促进的此类环化反应中，已达到出色的对映选择性水平（ee高达99％），从而导致了具有空前螺环结构的手性硫化物。然后通过随后的对酯基硫中心的高度非对映选择性氧化获得了相应的亚砜。