2,2,5,5-tetramethylpyrrolidine-3-carboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2,2,5,5-tetramethylpyrrolidine-3-carboxylic acid ethyl ester
• 英文别名: ethyl 2,2,5,5-tetramethyl-3-pyrrolidinecarboxylate；2,2,5,5-tetramethyl-pyrrolidine-3-carboxylic acid ethyl ester；2,2,5,5-Tetramethyl-pyrrolidin-3-carbonsaeure-aethylester；Ethyl 2,2,5,5-tetramethylpyrrolidine-3-carboxylate
• 化学式: C₁₁H₂₁NO₂
• 分子量: 199.293
• InChiKey: XPMJIDGVINDXNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2,5,5-tetramethylpyrrolidine-3-carboxylic acid ethyl ester 在 sodium tungstate 、 双氧水 、 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 生成 3-(Ethoxycarbonyl)-2,2,5,5-tetramethylpyrrolidin-1-oxyl
  参考文献：
  名称：

  Facile Synthesis of 3-Methoxycarbonyl-2,2,5,5-tetra-methylpyrrolidine-1-oxyl and Derivatives

  摘要：

  We have achieved an efficient alternative synthesis of blood-brain-barrier permeable nitroxyl radicals 3-methoxycarbonyl-2,2,5,5-tetramethylpyrrolidine-1-oxyl (1a) and 3-ethoxycarbonyl-2,2,5,5-tetramethylpyrrolidine-1-oxyl (1b), which affords la and 1b in 65% isolated yields by four steps from 2,2,6.6-tetramethyl-4-piperidone (2), respectively. This protocol is applicable to the synthesis of 3-isopropoxy-2,2,5,5-tetramethylpyrrolidine-1-oxyl (1c) and 3-carbonyl-2,2,5,5-tetramethylpyrro-lidine-1-oxyl (6).

  DOI：

  10.3987/com-09-11861
• 作为产物：
  描述：

  2,2,5,5-tetramethyl-2,5-dihydropyrrole-3-carboxylic acid ethyl ester 在 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 乙醇 为溶剂， 生成 2,2,5,5-tetramethylpyrrolidine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Facile Synthesis of 3-Methoxycarbonyl-2,2,5,5-tetra-methylpyrrolidine-1-oxyl and Derivatives

  摘要：

  We have achieved an efficient alternative synthesis of blood-brain-barrier permeable nitroxyl radicals 3-methoxycarbonyl-2,2,5,5-tetramethylpyrrolidine-1-oxyl (1a) and 3-ethoxycarbonyl-2,2,5,5-tetramethylpyrrolidine-1-oxyl (1b), which affords la and 1b in 65% isolated yields by four steps from 2,2,6.6-tetramethyl-4-piperidone (2), respectively. This protocol is applicable to the synthesis of 3-isopropoxy-2,2,5,5-tetramethylpyrrolidine-1-oxyl (1c) and 3-carbonyl-2,2,5,5-tetramethylpyrro-lidine-1-oxyl (6).

  DOI：

  10.3987/com-09-11861

文献信息

• Substituted Rylene Derivatives
  申请人：Konemann Martin

  公开号：US20080167467A1

  公开（公告）日：2008-07-10

  Rylene derivatives of the general formula I in which the variables are each defined as follows: Rylene is a polycyclic conjugated ring system which comprises at least one perylene unit may comprise heteroatoms as ring atoms, may be functionalized by moieties comprising —CO— groups and/or may bear further substituents other than the A radicals; A is a radical of the formula X is oxygen or sulfur; R are identical or different radicals: optionally substituted alkyl, cycloalkyl, aryl, hetaryl, —U-aryl where U is an —O—, —S—, —NR 2 —, —CO—, —SO— or —SO 2 — moiety, or C 1 -C 12 -alkoxy, C 1 -C 6 -alkylthio, —C≡CR 2 , —CR 2 ═CR 2 2 , hydroxy, mercapto, halogen, cyano, nitro, —NR 3 R 4 , —NR 3 COR 4 , —CONR 3 R 4 , —SO 2 NR 3 R 4 , —COOR 3 or —SO 3 R 3 ; R′ are identical or different radicals: hydrogen or one of the R radicals; R 2 is hydrogen or alkyl, where the R 2 radicals may be the same or different when they occur more than once; R 3 , R 4 are each independently hydrogen; optionally substituted alkyl, aryl or hetaryl; n is from 1 to 8.

  该公式的Rylene衍生物为I，其中变量的定义如下： Rylene是一个多环共轭环系统，包括至少一个苝并单元，可能包含杂原子作为环原子，可能被含有—CO—基团的基团所官能化，或者可能带有除A基团以外的其他取代基； A是公式的基团； X是氧或硫； R是相同或不同的基团：可选取代的烷基、环烷基、芳基、杂芳基、—U-芳基，其中U是—O—、—S—、—NR2—、—CO—、—SO—或—SO2—基团，或C1-C12-烷氧基、C1-C6-烷基硫基、—C≡CR2、—CR2═CR22、羟基、巯基、卤素、氰基、硝基、—NR3R4、—NR3COR4、—CONR3R4、—SO2NR3R4、—COOR3或—SO3R3； R′是相同或不同的基团：氢或R基团之一； R2是氢或烷基，当它们出现多次时，R2基团可以相同或不同； R3、R4各自独立地为氢；可选取代的烷基、芳基或杂芳基； n为1至8。
• Indirect electrochemical oxidation of piperidin-4-ones mediated by sodium halide-base system
  作者：Michail N. Elinson、Alexander S. Dorofeev、Sergey K. Feducovich、Ruslan F. Nasybullin、Evgeny F. Litvin、Mikhail V. Kopyshev、Gennady I. Nikishin

  DOI：10.1016/j.tet.2006.06.031

  日期：2006.8

  Indirect electrochemical oxidation of 1-N-subsituted piperidin-4-ones in methanol in an undivided cell in the presence of sodium iodide/sodium methoxide system leads to the corresponding alpha-hydroxyketals in 50-80% substance yield (50-65% current yield). 2,2,6,6Tetramethylpiperidin-4-one under the same conditions forms a mixture of methyl 2,2,5,5-tetramethyl-3-pyrrolidinecarboxylate and methyl 2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrole-3-carboxylate in 70% substance yield (60-70% current yield) via electrochemically induced Favorskii rearrangement. (c) 2006 Elsevier Ltd. All rights reserved.
• Rylene Tetracarboxylic Acid Diimides Substituted By Cyclic Amino Groups
  申请人：Konemann Martin

  公开号：US20090124732A1

  公开（公告）日：2009-05-14

  Rylenetetracarboximides of the general formula I in which the variables are each defined as follows: R, R′ are each independently hydrogen; optionally substituted C 1 -C 30 -alkyl, C 3 -C 8 -cycloalkyl, aryl or hetaryl; R 1 is hydrogen or C 1 -C 6 -alkyl; R 2 , R 3 are each independently hydrogen; optionally substituted C 1 -C 18 -alkyl, aryl or hetaryl; A is a 5- to 9-membered ring which is bonded via a nitrogen atom and whose carbon chain may be interrupted by one or more —O—, —S—, —NR 1 —, —CO— and/or —SO 2 — moieties, to which one or two unsaturated or saturated 4 - to 8 -membered rings may be fused, whose carbon chain may likewise be interrupted by these moieties and/or —N═, and the overall ring system may be mono- or polysubstituted, and where the A radicals may be the same or different when m>1; X is chlorine or bromine, and the X radicals may be the same or different when x>1; Z is optionally substituted C 3 -C 20 -alkyl, C 3 -C 20 -alken-2-yl, C 3 -C 20 -alkyn-2-yl, aryloxy, arylthio, hetaryloxy or hetarylthio, where the Z radicals may be the same or different when z>1; m is 1 or 2, n is from 1 to 4 when m=1; is from 1 to 6 when m=2; x is from 0 to 3 when m=1, where n+x+z≦4, is from 0 to 5 when m=2, where n+x+z≦6; z is from 0 to 3 when m=1, where n+x+z≦4, is from 0 to 5 when m=2, where n+x+z≦6.
• USE OF RYLENES AS MARKERS FOR LIQUIDS
  申请人：Gessner Thomas

  公开号：US20100011656A1

  公开（公告）日：2010-01-21

  The invention relates to the use of rylene derivatives of the general formula (I) as markers for liquids, where the symbols and indices have the meanings given in the specification.
• US8071775B2
  申请人：——

  公开号：US8071775B2

  公开（公告）日：2011-12-06