4,4'-p-phenylenebis(valeroyl chloride) | 78704-75-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4'-p-phenylenebis(valeroyl chloride)
• 英文别名: 5-[4-(5-chloro-5-oxopentyl)phenyl]pentanoyl chloride
• CAS: 78704-75-3
• 化学式: C₁₆H₂₀Cl₂O₂
• 分子量: 315.24
• InChiKey: SLYWCVUIOUNTGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  20.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4,4'-p-phenylenebis(valeroyl chloride) 在 四氯化锡 、 苯甲醇钠 、 diborane(6) 作用下， 以 四氢呋喃 、 硝基甲烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Tang, Hang; Wijesekera, Tilak P.; Dolphin, David, Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1366 - 1374

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4-双(3-溴丙基)苯 在 氢氧化钾 、 氯化亚砜 、 sodium ethanolate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4,4'-p-phenylenebis(valeroyl chloride)
  参考文献：
  名称：

  Tang, Hang; Wijesekera, Tilak P.; Dolphin, David, Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1366 - 1374

  摘要：

  DOI：

文献信息

• Synthesis of 6,21-dioxo-5,22-diaza[10.10]paracyclophane and its structural characteristics
  作者：Hiroki Kondo、Hiroshi Okamoto、Jun-Ichi Kikuchi、Junzo Sunamoto

  DOI：10.1039/p19810003125

  日期：——

  A novel paracyclophane, 6,21-dioxo-5,22-diaza[10.10]paracyclophane (4) has been synthesized by a condensation of 5,5′-p-phenylenebis (valeroyl chloride)(5) with 4,4′-p-phenylenebis(butylamine)(3) by a high dilution method. It has been characterized by means of u.v., i.r., and n.m.r. spectroscopy. The two amide bonds in compound (4) were found to assume the s-trans-geometry. No significant transannular

  通过将5,5'-对亚苯基（戊酰氯）（5）与4,4'-缩合合成了一种新型的对环烷，6,21-二氧杂-5,22-二氮杂[10.10]对环烷（4）。对苯二双（丁胺）（3）的高稀释法。它已经通过紫外，红外和核磁共振光谱进行了表征。发现化合物（4）中的两个酰胺键呈s-反式-几何构型。在两个苯环之间未观察到明显的跨环相互作用。冷却后，通过将nmr环质子信号分裂为双峰，可以证明苯环的旋转受到阻碍。在30±5°C的聚结温度下，该旋转受阻的活化能评估为0.9 kcal / mol。
• Convenient Synthesis of Chiral Cyclophanes that Can Coordinate to Metals
  作者：Masayuki Sato、Fumiaki Uehara、Kayo Sato、Masahiko Yamaguchi、Chizuko Kabuto

  DOI：10.1021/ja983907u

  日期：1999.9.1

  Optically pure cyclophanes possessing a 1,3-dicarbonyl moiety were conveniently synthesized from alkanedioyl dichloride in four steps. The intramolecular [4+2]cycloaddition of bis(acylketene)s generated by thermal decomposition of bis(4,6-dioxo-1,3-dioxane) proceeded smoothly, giving cyclophane pyranones in high yields. The compounds possessing 7-10 bridging methylenes were resolved by imine formation with (R)-1-phenylethylamine, followed by basic hydrolysis. These cyclophanes are optically active versions of acetylacetone or salicylaldehyde and formed complexes with metals such as copper and europium. X-ray analysis of the chiral copper complex indicated the pentacoordinated structure of the copper metal with syn configuration of the two bridging chains.
• Bivalent Smac Mimetics with a Diazabicyclic Core as Highly Potent Antagonists of XIAP and cIAP1/2 and Novel Anticancer Agents
  作者：Yuefeng Peng、Haiying Sun、Jianfeng Lu、Liu Liu、Qian Cai、Rong Shen、Chao-Yie Yang、Han Yi、Shaomeng Wang

  DOI：10.1021/jm201072x

  日期：2012.1.12

  Nonpeptidic, bivalent Smac mimetics designed based upon monovalent Smac mimetics with a diazabicyclic core structure bind to XIAP, cIAP1, and cIAP2 with low to subnanomolar affinities and are highly effective in antagonizing XIAP in cell-free functional assays. They efficiently induce the degradation of cIAP1 and cIAP2 in cancer cells at concentrations as low as 1 nM, activate caspase-3 and -8, and cleave PARP at 3-10 nM. The most potent compounds in the series have IC50 of 3-5 nM in inhibition of cell growth in both MDA-MB-231and SK-OV-3 cell lines and are promising lead compounds for the development of a new class of cancer therapy.
• Staab, Heinz A.; Ippen, Joachim; Tao-pen, Chu, Angewandte Chemie, 1980, vol. 92, # 1, p. 49 - 51
  作者：Staab, Heinz A.、Ippen, Joachim、Tao-pen, Chu、Krieger, Claus、Starker, Barbara

  DOI：——

  日期：——
• KONDO, HIROKI;OKAMOTO, HIROSHI;KIKUCHI, JUN-ICHI;SUNAMOTO, JUNZO, J. CHEM. SOC. PERKIN TRANS., 1981, N 12, 3125-3128
  作者：KONDO, HIROKI、OKAMOTO, HIROSHI、KIKUCHI, JUN-ICHI、SUNAMOTO, JUNZO

  DOI：——

  日期：——