2,3-dimethyl-7,8-diethyl-10H-dipyrrin-1-one-9-carboxylic acid | 270928-63-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,3-dimethyl-7,8-diethyl-10H-dipyrrin-1-one-9-carboxylic acid
• 英文别名: 7,8-diethyl-2,3-dimethyl-dipyrrin-1-one-9 carboxylic acid
• CAS: 270928-63-7
• 化学式: C₁₆H₂₀N₂O₃
• 分子量: 288.346
• InChiKey: HFXKTBDDMYEFSS-GHXNOFRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  82.19
• 氢给体数：
  3.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,3-dimethyl-7,8-diethyl-10H-dipyrrin-1-one-9-carboxylic acid 在 sodium hydroxide 、 sodium tetrahydroborate 、 potassium acetate 、 sodium acetate 、 四氯化锡 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 9.67h， 生成 9-[2-(carboxyethyl)benzyl]-3,4-dimethyl-7,8-diethyl-dipyrrinone
  参考文献：
  名称：

  Stereochemistry and Conformational Analysis of Hemirubin

  摘要：

  Intramolecularly hydrogen-bonded analogs of the natural bile pigment, bilirubin, are very scarce. Nuclear Overhauser effect NMR studies of the newest analog, a hemirubin (1), confirms intramolecular hydrogen bonding and a ridge-tile-shaped conformation. H-1 NMR studies of 1 at sufficiently low temperatures detect conformational enantiomerization, for which an activation barrier of Delta G(double dagger)similar to 16 kcal/mol at 25 degrees C in CDCl3 has been estimated. Evidence for the presence of dimeric association at low temperatures or high concentrations of 1 is found by the appearance of new sets of resonances, data from which may be used to calculate: Delta G degrees(298) (K) + 3.4 kca/mol, Delta H degrees - 5.6 kcal/mol and Delta S degrees -30.3 cal/deg/mol. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00087-9
• 作为产物：
  描述：

  3,4-二乙基-5-甲基-2-吡咯羧酸乙酯 在 氢氧化钾 、 Ce(NH₃)2(NO₃)4 作用下， 以 四氢呋喃 、 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 6.0h， 生成 2,3-dimethyl-7,8-diethyl-10H-dipyrrin-1-one-9-carboxylic acid
  参考文献：
  名称：

  Stereochemistry and Conformational Analysis of Hemirubin

  摘要：

  Intramolecularly hydrogen-bonded analogs of the natural bile pigment, bilirubin, are very scarce. Nuclear Overhauser effect NMR studies of the newest analog, a hemirubin (1), confirms intramolecular hydrogen bonding and a ridge-tile-shaped conformation. H-1 NMR studies of 1 at sufficiently low temperatures detect conformational enantiomerization, for which an activation barrier of Delta G(double dagger)similar to 16 kcal/mol at 25 degrees C in CDCl3 has been estimated. Evidence for the presence of dimeric association at low temperatures or high concentrations of 1 is found by the appearance of new sets of resonances, data from which may be used to calculate: Delta G degrees(298) (K) + 3.4 kca/mol, Delta H degrees - 5.6 kcal/mol and Delta S degrees -30.3 cal/deg/mol. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00087-9

文献信息

• Amide to carboxylic acid hydrogen bonding. The dipyrrinone receptor
  作者：Michael T. Huggins、Nicholas T. Salzameda、David A. Lightner

  DOI：10.1080/10610278.2010.521836

  日期：2011.3.1

  Hydrogen bonding between carboxylic acid and amide groups was demonstrated for a series of amides called [n]-semirubins consisting of a dipyrrinone attached to the end of an n-carbon alkanoic acid. Such hydrogen bonding is more effective than the alternative amide to amide or acid to acid types for all of the semirubins studied: n = 1, 3–7, 10 and 20. As determined by 1H NMR and vapour pressure osmometry

  羧酸和酰胺基团之间的氢键已被一系列称为 [n]-半红素的酰胺证明，该酰胺由连接到 n-碳链烷酸末端的双吡喃酮组成。对于所有研究的半红宝石，这种氢键比替代酰胺到酰胺或酸到酸类型更有效：n = 1、3-7、10 和 20。根据 1H NMR 和蒸气压渗透法测定，[n]-半红素，其中 n = 5–20，在 CHCl3 或 CDCl3 中以分子内氢键键合；[4]-半红素是分子间氢键的二聚体；[3]-半红素是四聚体；和 [1]-半红素是一种二聚体——所有的都与羧酸和酰胺形成氢键。双吡喃酮酰胺和相邻的吡咯构成了羧酸基团的有效受体。
• Hydrogen-Bonded Dimers in Dipyrrinones and Acyldipyrrinones
  作者：Michael T. Huggins、David A. Lightner

  DOI：10.1007/s007060170131

  日期：2001.2.15

  as determined by analysis of variable temperature 1H NMR data. In contrast, when the 9-acyl group is replaced by formyl or when the acyl group is fixed in a syn orientation to the pyrrole NH, the dipyrrinone is strongly prone to dimerization in CHCl3.

  9-酰基-二吡咯烷酮9-丁酰基-2,3,7,8-四甲基-（10 H ）-二吡喃-1-酮的晶体结构测定 表明存在分子间氢键合的二聚体。然而，在CHCl 3溶液中，颜料是单体的，如通过蒸气压渗透压测量法测定的。在C（8），9酰基dipyrrinone仅表现出弱的倾向，在CHCl形成二聚体缺少的烷基3（ ķ 甲 〜60  中号 -1如通过可变温度的分析测定）1 H NMR数据。相反，当9-酰基被甲酰基取代时或当酰基固定在 合成物中时 在吡咯NH的方向上，二吡啶酮在CHCl 3中强烈倾向于二聚。