2-methyl-2-(β-carboxyethyl)cyclopentene-1,3-dione | 5895-65-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-2-(β-carboxyethyl)cyclopentene-1,3-dione
• 英文别名: 3-(1-methyl-2,5-dioxocyclopentyl)propanoic acid；2-Methyl-2-<2-carboxyethyl>-cyclopentandion-(1.3)；3-(1-Methyl-2,5-dioxocyclopentyl)-propionic acid；(1-Methyl-2,5-dioxo-cyclopentyl)-propionsaeure
• CAS: 5895-65-8
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: BTVJOTVZSLWBTL-UHFFFAOYSA-N

物化性质

• 熔点：
  126 °C
• 沸点：
  388.1±22.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-2-(β-carboxyethyl)cyclopentene-1,3-dione 在 sodium hydroxide 作用下， 生成 4-甲基-5-氧代辛二酸
  参考文献：
  名称：

  Schick,H. et al., Journal fur praktische Chemie (Leipzig 1954), 1977, vol. 319, p. 213 - 218

  摘要：

  DOI：
• 作为产物：
  描述：

  tert-butyl 3-(1-methyl-2,5-dioxocyclopentyl)propanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以99%的产率得到2-methyl-2-(β-carboxyethyl)cyclopentene-1,3-dione
  参考文献：
  名称：

  Selective Derivatization of N-Terminal Cysteines Using Cyclopentenediones

  摘要：

  The outcome of the Michael-type reaction between thiols and 2,2-disubstituted cyclopentenediones varies depending on the thiol. Stable compounds with two fused rings were formed upon reaction with 1,2-aminothiols (such as N-terminal cysteines in peptides). Other thiols gave reversibly Michael-type adducts that were in equilibrium with the starting materials. This differential reactivity allows differently placed cysteines to be distinguished and has been exploited to prepare bioconjugates incorporating two or three different moieties.

  DOI：

  10.1021/acs.orglett.6b02301

文献信息

• Synthesis in the diazasteroid group. XIII. Synthesis of 8,10-diaza-estrane.
  作者：HIROKI TAKAHATA、HIDEO OKAJIMA、MASANORI NAGATA、TAKAO YAMAZAKI

  DOI：10.1248/cpb.28.984

  日期：——

  Reductive condensation of the amine (5) with the acid (2), followed by reduction of the carbonyl group and pyridine ring gave the cis-seco-8, 10-diazasteroid (12). Reductive cyclization of 12 with lithium aluminum hydride afforded two configurational isomers (14a, b) of 8, 10-diaza-estran. The stereochemistry of both isomers is discussed.

  胺（5）与酸（2）进行还原缩合，然后还原羰基和吡啶环，得到顺式-雌甾-8，10-二氮杂环（12）。用氢化铝锂对 12 进行还原环化，可得到 8，10-二氮杂雌甾的两种构型异构体（14a，b）。本文讨论了这两种异构体的立体化学。
• Schick, Hans; Roatsch, Birgit; Schwarz, Hartmut, Liebigs Annalen der Chemie, 1992, # 5, p. 419 - 422
  作者：Schick, Hans、Roatsch, Birgit、Schwarz, Hartmut、Hauser, Andre、Schwarz, Sigfrid

  DOI：——

  日期：——
• BONDON D.; PUCCI B.; PIETRASANTA Y., C. R. ACAD. SCI. <CHDC-AQ>, 1976, C282, NO 19, 951-953
  作者：BONDON D.、 PUCCI B.、 PIETRASANTA Y.

  DOI：——

  日期：——
• Selective Derivatization of <i>N</i>-Terminal Cysteines Using Cyclopentenediones
  作者：Omar Brun、Jordi Agramunt、Lluis Raich、Carme Rovira、Enrique Pedroso、Anna Grandas

  DOI：10.1021/acs.orglett.6b02301

  日期：2016.10.7

  The outcome of the Michael-type reaction between thiols and 2,2-disubstituted cyclopentenediones varies depending on the thiol. Stable compounds with two fused rings were formed upon reaction with 1,2-aminothiols (such as N-terminal cysteines in peptides). Other thiols gave reversibly Michael-type adducts that were in equilibrium with the starting materials. This differential reactivity allows differently placed cysteines to be distinguished and has been exploited to prepare bioconjugates incorporating two or three different moieties.
• Schick,H. et al., Journal fur praktische Chemie (Leipzig 1954), 1977, vol. 319, p. 213 - 218
  作者：Schick,H. et al.

  DOI：——

  日期：——