2,4-dimethyl-3-isobutyl-5-carboethoxypyrrole | 4989-24-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,4-dimethyl-3-isobutyl-5-carboethoxypyrrole
• 英文别名: 4-isobutyl-3,5-dimethyl-pyrrole-2-carboxylic acid ethyl ester；2,4-Dimethyl-3-isobutyl-5-carbethoxy-pyrrole；ethyl 4-isobutyl-3,5-dimethyl-1H-pyrrole-2-carboxylate；ethyl 3,5-dimethyl-4-(2-methylpropyl)-1H-pyrrole-2-carboxylate
• CAS: 4989-24-6
• 化学式: C₁₃H₂₁NO₂
• mdl: MFCD02642495
• 分子量: 223.315
• InChiKey: LUNFYIYRSZNSKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-dimethyl-3-isobutyl-5-carboethoxypyrrole 在 sodium hydroxide 、 氰基磷酸二乙酯 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 ethyl 2-[[3,5-dimethyl-4-(2-methylpropyl)-1H-pyrrole-2-carbonyl]amino]acetate
  参考文献：
  名称：

  Synthesis and aldose reductase inhibitory activity of acetic acid derivatives of pyrrolo[1,2-c]imidazole

  摘要：

  Various acetic acid derivatives of pyrrolo[1,2-c]imidazole were prepared and evaluated for aldose reductase inhibitory activity. Most of the compounds inhibited aldose reductase isolated from rat lens in vitro and decreased sorbitol formation in sciatic nerves of diabetic rats in vivo. Of the test compounds, 2-carboxymethyl-6-ethyl-5,7-dimethyl-3-oxo-1(2H)-thioxo-1H-pyrrolo[1,2-c] imidazole 124 was found to be the most orally active aldose reductase inhibitor, with an inhibitory potency similar to that of AD-5467.

  DOI：

  10.1016/0223-5234(93)90016-8
• 作为产物：
  描述：

  异丁酰基丙酮 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 sodium acetate 、 锌 、 sodium nitrite 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 2,4-dimethyl-3-isobutyl-5-carboethoxypyrrole
  参考文献：
  名称：

  由不对称β-二酮合成区域选择性吡咯并转化为位阻卟啉

  摘要：

  不对称的β-二酮与α-氧亚氨基乙酰乙酸酯的缩合可选择性地提供吡咯。使用13 C-NMR光谱研究了区域选择性的机理。通过该方法合成在4-位​​具有新戊基的吡咯，并以良好的收率将其进一步转化为位阻卟啉。

  DOI：

  10.1016/s0040-4039(97)00039-7

文献信息

• Alkylation process
  申请人：Canadian Patents & Development Limited

  公开号：US04070366A1

  公开（公告）日：1978-01-24

  Substituted pyrrole compounds, such as 3-ethyl-4-methyl-5-carbethoxy pyrrole, 2,4-dimethyl-3-acetyl pyrrole and 2-methyl-5-carboxy pyrrole-4-propionic acid diethyl ester, are alkylated in a single step by reaction with an aldehyde or ketone in the presence of both an acid condensing agent such as hydriodic acid and a compatible reducing agent such as metallic zinc or stannous chloride. Suitable carbonyl reactants include formaldehyde, paraldehyde, isobutyraldehyde, acetone, cyclohexanone and methyl-isobutyl ketone. This application is a continuation application of U.S. application Ser. No. 281,624 filed Aug. 18, 1972, now abandoned, which is a continuation-in-part application of U.S. application Ser. No. 832,001, filed June 10, 1969, now abandoned.

  取代吡咯类化合物，如3-乙基-4-甲基-5-羰基乙酸酯吡咯、2,4-二甲基-3-乙酰基吡咯和2-甲基-5-羧基吡咯-4-丙酸二乙酯，可通过与醛或酮在存在酸性缩合剂（如碘化氢）和兼容的还原剂（如金属锌或氯化亚锡）的情况下进行一步反应进行烷基化。适合的羰基反应物包括甲醛、对甲醛、异丁醛、丙酮、环己酮和甲基异丁基酮。本申请是美国1972年8月18日申请的第281,624号专利申请的继续申请，该专利申请已被放弃，是美国1969年6月10日申请的第832,001号专利申请的续展部分申请。
• 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。
• US4070366A
  申请人：——

  公开号：US4070366A

  公开（公告）日：1978-01-24
• Synthesis and aldose reductase inhibitory activity of acetic acid derivatives of pyrrolo[1,2-c]imidazole
  作者：I Yamawaki、Y Matsushita、N Asaka、K Ohmori、N Nomura、K Ogawa

  DOI：10.1016/0223-5234(93)90016-8

  日期：1993.1

  Various acetic acid derivatives of pyrrolo[1,2-c]imidazole were prepared and evaluated for aldose reductase inhibitory activity. Most of the compounds inhibited aldose reductase isolated from rat lens in vitro and decreased sorbitol formation in sciatic nerves of diabetic rats in vivo. Of the test compounds, 2-carboxymethyl-6-ethyl-5,7-dimethyl-3-oxo-1(2H)-thioxo-1H-pyrrolo[1,2-c] imidazole 124 was found to be the most orally active aldose reductase inhibitor, with an inhibitory potency similar to that of AD-5467.
• Regioselective pyrrole synthesis from asymmetric β-diketone and conversion to sterically hindered porphyrin
  作者：Hiroshi Fujii、Tetsuhiko Yoshimura、Hitoshi Kamada

  DOI：10.1016/s0040-4039(97)00039-7

  日期：1997.2

  The condensation of asymmetric β-diketones with α-oximinoacetoacetate esters affords pyrroles regioselectively. The mechanism of the regioselectivity is studied using 13C-NMR spectroscopy. Pyrrole having a neopentyl group at the 4-position is synthesized by the method, and further converted to a steric hindered porphyrin in good yield.

  不对称的β-二酮与α-氧亚氨基乙酰乙酸酯的缩合可选择性地提供吡咯。使用13 C-NMR光谱研究了区域选择性的机理。通过该方法合成在4-位​​具有新戊基的吡咯，并以良好的收率将其进一步转化为位阻卟啉。