(3-chloropropyl)bis(2-methoxyethyl)amine | 959243-79-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (3-chloropropyl)bis(2-methoxyethyl)amine
• 英文别名: 3-(N,N-bis-2-methoxyethyl-amino)-propyl chloride；Propylamine, 3-chloro-N,N-bis(2-methoxyethyl)-；3-chloro-N,N-bis(2-methoxyethyl)propan-1-amine
• CAS: 959243-79-9
• 化学式: C₉H₂₀ClNO₂
• 分子量: 209.716
• InChiKey: ZLLPKVOYKHIVOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3-chloropropyl)bis(2-methoxyethyl)amine 、 环戊二烯 在 sodium 、 甲基锂 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醚 为溶剂， 反应 16.0h， 生成 {3-[bis(2-methoxyethyl)amino]propyl}cyclopentadienyllithium
  参考文献：
  名称：

  Internally Solvated Cyclopentadienyllithium Compounds:  Structural Integrity of the Cp^-Li⁺ Moiety. NMR, Dynamics, X-ray Crystallography, and Calculations

  摘要：

  Three cyclopentadienyllithium compounds with the tethered, T, ligand -N(CH2CH2OCH3)(2) are as follows: T = CHCH(CH3)(2),6; T = (CH2)(2), 10; T = (CH2)(3),14. The results of NOE NMR experiments for 6, 10, and 14 together with X-ray crystallography of 14 support internally coordinated monomeric structures for all three compounds. Models have been constructed for 6, 10, and 14 from modifications of an internally solvated allylic lithium compound at the B3LYP level of theory using basis set 6-311G*. The resulting structural features are very similar to those obtained from the NMR and crystallographic data. In addition, C-13 NMR shifts obtained with the GIAO procedure using the results of the B3LYP/6-311G* calculations are closely similar to the experimental shifts, which validate B3LYP as a suitable model for these compounds. The Li+ centroid distance of ca. 1.9 angstrom to 2.0 angstrom obtained for 6, 10, and 14 is common to most crystallographic data for externally solvated Cp-Li+ compounds as well as one which incorporates a (CpLiCp)(-) triple ion. It is concluded that the ligand tether and the stereochemistry around Li+ accommodate to maintain the structural integrity of Cp-Li+. NMR and crystallography show 14 to be chiral. Carbon-13 NMR line shape changes are attributed to inversion via a lateral wobble mechanism with Delta H-double dagger = 6 kcal(.)mol(-1) and Delta S-double dagger = -2 eu. It is also shown that a 6,6-dimethylfulvene is deprotonated at methyl by LiN(CH2-CH2OCH3)(3) as well as by butyllithium in the presence of PMDTA producing isopropenyl Cp-Li+ compounds 24 and 25, respectively. NMR line shape changes of the sample containing 24 have been qualitatively interpreted to result from a combination of fast transfer of coordinated ligand between faces of the carbanion plane as well as a lithium-exchange process.

  DOI：

  10.1021/jo0512507
• 作为产物：
  描述：

  diethyl 2-amino-6-[(hydroxycarbamoyl)-methyl]-azulene-1,3-dicarboxylate sodium 以49%的产率得到diethyl 2-amino-6-{[3-(N,N-bis-2-methoxyethyl-amino)-propoxycarbamoyl]-methyl}-azulene-1,3-dicarboxylate
  参考文献：
  名称：

  Azulene derivatives

  摘要：

  该发明提供了一种通式I的新型蓝紫烯衍生物##STR1##其中R.sub.1至R.sub.6在描述中给出的含义，以及它们的互变异构体、对映异构体、非对映异构体、消旋体和生理兼容性盐或酯，以及在体内水解或代谢为通式I化合物的物质。该发明还涉及制备上述化合物的过程和中间体，含有这些化合物的药物组合物，以及在治疗炎症性疾病中使用这些化合物。

  公开号：

  US06121322A1

文献信息

• AZULENE HYDROXAMIC ACID DERIVATIVES AS METALLOPROTEIN INHIBITORS
  申请人：Roche Diagnostics GmbH

  公开号：EP1054878A1

  公开（公告）日：2000-11-29
• US6121322A
  申请人：——

  公开号：US6121322A

  公开（公告）日：2000-09-19
• [EN] AZULENE HYDROXAMIC ACID DERIVATIVES AS METALLOPROTEIN INHIBITORS<br/>[FR] UTILISATION DE DERIVES D'ACIDE HYDROXAMIDE D'AZULENE COMME INHIBITEUR DE METALLOPROTEINES
  申请人：ROCHE DIAGNOSTICS GMBH

  公开号：WO1999031078A1

  公开（公告）日：1999-06-24

  (EN) The invention provides novel azulene derivatives of general formula (I) wherein R1 to R6 have the significance given in the description, as well as their tautomers, enantiomers, diastereomers, racemates and physiologically compatible salts or esters and substances which are hydrolyzed or metabolised $i(in vivo) to compounds of formula (I). The invention is also concerned with a process and intermediates for the manufacture of the above compounds, medicaments which contain such compounds as well as the use of these compounds in the production of medicaments having metalloprotein-inhibiting activity.(FR) La présente invention concerne de nouveaux dérivés d'azulène représentés par la formule générale (I), dans laquelle R1 à R6 sont tels que définis dans la description, de même que pour leurs tautomères, énantiomères, diastéréomères, racémates et sels et esters physiologiquement compatibles, ainsi que des substances hydrolysées ou métabolisées in vivo en composés de la formule (I). Cette invention concerne par ailleurs un procédé et des produits intermédiaires utilisés dans la fabrication des composés précités, des médicaments contenant de tels composés, ainsi que l'utilisation de ces composés dans la production de médicaments ayant une activité inhibitrice des métalloprotéines.
• Azulene derivatives
  申请人：Boehringer Mannheim GmbH

  公开号：US06121322A1

  公开（公告）日：2000-09-19

  The invention provides novel azulene derivatives of general formula I ##STR1## wherein R.sub.1 to R.sub.6 have the significance given in the description, as well as their tautomers, enantiomers, diastereomers, racemates and physiologically compatible salts or esters and substances which are hydrolyzed or metabolized in vivo to compounds of formula I. The invention is also concerned with a process and intermediates for the manufacture of the above compounds, pharmaceutical compositions which contain such compounds as well as the use of these compounds in the treatment of inflammatory conditions.

  该发明提供了一种通式I的新型蓝紫烯衍生物##STR1##其中R.sub.1至R.sub.6在描述中给出的含义，以及它们的互变异构体、对映异构体、非对映异构体、消旋体和生理兼容性盐或酯，以及在体内水解或代谢为通式I化合物的物质。该发明还涉及制备上述化合物的过程和中间体，含有这些化合物的药物组合物，以及在治疗炎症性疾病中使用这些化合物。
• Internally Solvated Cyclopentadienyllithium Compounds:  Structural Integrity of the Cp^-Li⁺ Moiety. NMR, Dynamics, X-ray Crystallography, and Calculations
  作者：Gideon Fraenkel、Xiao Chen、Albert Chow、Judith C. Gallucci、Hua Liu

  DOI：10.1021/jo0512507

  日期：2005.11.1

  Three cyclopentadienyllithium compounds with the tethered, T, ligand -N(CH2CH2OCH3)(2) are as follows: T = CHCH(CH3)(2),6; T = (CH2)(2), 10; T = (CH2)(3),14. The results of NOE NMR experiments for 6, 10, and 14 together with X-ray crystallography of 14 support internally coordinated monomeric structures for all three compounds. Models have been constructed for 6, 10, and 14 from modifications of an internally solvated allylic lithium compound at the B3LYP level of theory using basis set 6-311G*. The resulting structural features are very similar to those obtained from the NMR and crystallographic data. In addition, C-13 NMR shifts obtained with the GIAO procedure using the results of the B3LYP/6-311G* calculations are closely similar to the experimental shifts, which validate B3LYP as a suitable model for these compounds. The Li+ centroid distance of ca. 1.9 angstrom to 2.0 angstrom obtained for 6, 10, and 14 is common to most crystallographic data for externally solvated Cp-Li+ compounds as well as one which incorporates a (CpLiCp)(-) triple ion. It is concluded that the ligand tether and the stereochemistry around Li+ accommodate to maintain the structural integrity of Cp-Li+. NMR and crystallography show 14 to be chiral. Carbon-13 NMR line shape changes are attributed to inversion via a lateral wobble mechanism with Delta H-double dagger = 6 kcal(.)mol(-1) and Delta S-double dagger = -2 eu. It is also shown that a 6,6-dimethylfulvene is deprotonated at methyl by LiN(CH2-CH2OCH3)(3) as well as by butyllithium in the presence of PMDTA producing isopropenyl Cp-Li+ compounds 24 and 25, respectively. NMR line shape changes of the sample containing 24 have been qualitatively interpreted to result from a combination of fast transfer of coordinated ligand between faces of the carbanion plane as well as a lithium-exchange process.