1-[6-(4-Formyl-2-methoxyphenoxy)hexyl]indole-5-carbaldehyde | 1287199-75-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-[6-(4-Formyl-2-methoxyphenoxy)hexyl]indole-5-carbaldehyde
• 英文别名: 1-[6-(4-formyl-2-methoxyphenoxy)hexyl]indole-5-carbaldehyde
• CAS: 1287199-75-0
• 化学式: C₂₃H₂₅NO₄
• 分子量: 379.456
• InChiKey: HALBMLMGYJCDHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[6-(4-Formyl-2-methoxyphenoxy)hexyl]indole-5-carbaldehyde 在 吡啶 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 cis-20-methoxy-18-oxa-11-azatetracyclo[17.2.2.1^4,8.0^7,11]tetracosa-1⁽²¹⁾,4⁽²⁴⁾,5,7,9,19,22-heptaene-2,3-diyl diacetate
  参考文献：
  名称：

  p,p-Dihydroxydihydrostilbenophanes Related to Antimitotic Combretastatins. Conformational Analysis and Its Relationship to Tubulin Inhibition

  摘要：

  The structures of a new family of macrocyclic analogues of combretastatins B combining oxygenated substituents on the phenyl rings and indole rings are described. The effects of the stereochemistry, of the length of the spacer linking both aryl groups, and of the decoration of the macrocycles on the kinematics of the system have been studied by means of NMR studies at several temperatures and in different solvents combined with theoretical studies including Monte Carlo conformational searches and molecular dynamics simulations at different temperatures. The new indole macrocycles provide a more rigid view of this kind of macrocycles than that previously held. The tubulin polymerization activity of this new class of macrocycles has been assayed and analyzed.

  DOI：

  10.1021/jo500798r
• 作为产物：
  描述：

  5-吲哚甲醛 在 四丁基硫酸氢铵 、 potassium carbonate 、 sodium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.5h， 生成 1-[6-(4-Formyl-2-methoxyphenoxy)hexyl]indole-5-carbaldehyde
  参考文献：
  名称：

  新的对位对苯二酚：McMurry偶联合成，构象分析和微管蛋白聚合反应的抑制作用

  摘要：

  通过使用McMurry方法，合成了由3-氧杂戊基亚甲基-1,5-二氧基和六亚甲基-1,6-二氧基桥连接的新的甲氧基取代的[2.7]-和[2.8]对环环烷家族。还合成了相关的吲哚化合物。烯烃与二醇的比例取决于桥的长度，芳环的结构和反应条件。如通过NMR光谱法和根据理论计算所观察到的，大环化，甲氧基取代基和刚性吲哚部分的存在限制了构象平衡。合成的化合物显示微摩尔微管蛋白聚合抑制活性。与康布雷他汀，密切相关的斯蒂芬类相比，对大环化产生的微管蛋白聚合抑制活性的构象影响

  DOI：

  10.1002/chem.201002869

文献信息

• New para-para Stilbenophanes: Synthesis by McMurry Coupling, Conformational Analysis and Inhibition of Tubulin Polymerisation
  作者：Raquel Álvarez、Vilmarí López、Carmen Mateo、Manuel Medarde、Rafael Peláez

  DOI：10.1002/chem.201002869

  日期：2011.3.14

  The synthesis of a new family of methoxy‐substituted [2.7]‐ and [2.8]paracyclophanes linked by 3‐oxapentamethylene‐1,5‐dioxy and hexamethylene‐1,6‐dioxy bridges has been carried out by using the McMurry methodology. Related indole compounds were also synthesised. Olefin‐to‐diol ratios depended on the bridge length, the structure of the aromatic ring and the reaction conditions. Macrocyclisation, the

  通过使用McMurry方法，合成了由3-氧杂戊基亚甲基-1,5-二氧基和六亚甲基-1,6-二氧基桥连接的新的甲氧基取代的[2.7]-和[2.8]对环环烷家族。还合成了相关的吲哚化合物。烯烃与二醇的比例取决于桥的长度，芳环的结构和反应条件。如通过NMR光谱法和根据理论计算所观察到的，大环化，甲氧基取代基和刚性吲哚部分的存在限制了构象平衡。合成的化合物显示微摩尔微管蛋白聚合抑制活性。与康布雷他汀，密切相关的斯蒂芬类相比，对大环化产生的微管蛋白聚合抑制活性的构象影响
• <i>p</i>,<i>p</i>-Dihydroxydihydrostilbenophanes Related to Antimitotic Combretastatins. Conformational Analysis and Its Relationship to Tubulin Inhibition
  作者：Raquel Álvarez、Vilmarí López、Carmen Mateo、Manuel Medarde、Rafael Peláez

  DOI：10.1021/jo500798r

  日期：2014.8.1

  The structures of a new family of macrocyclic analogues of combretastatins B combining oxygenated substituents on the phenyl rings and indole rings are described. The effects of the stereochemistry, of the length of the spacer linking both aryl groups, and of the decoration of the macrocycles on the kinematics of the system have been studied by means of NMR studies at several temperatures and in different solvents combined with theoretical studies including Monte Carlo conformational searches and molecular dynamics simulations at different temperatures. The new indole macrocycles provide a more rigid view of this kind of macrocycles than that previously held. The tubulin polymerization activity of this new class of macrocycles has been assayed and analyzed.