2,3-dimethyl-5-methylene-4-oxo-cyclopent-2-enecarboxylic acid methyl ester | 77943-22-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3-dimethyl-5-methylene-4-oxo-cyclopent-2-enecarboxylic acid methyl ester
• 英文别名: 2,3-dimethyl-4-methoxycarbonyl-5-methylene-2-cyclopentenone；(+/-)-Desepoxy-2,5-didehydromethylenomycin A methyl ester；(+/-)-desepoxy-4,5-didehydromethylenomicin A methyl ester；(+/-)-deepoxy-4,5-didehydromethylenomycin A methyl ester；(d,l)-desepoxymethylenomycin A methyl ester；Methyl 2,3-dimethyl-5-methylidene-4-oxocyclopent-2-ene-1-carboxylate
• CAS: 77943-22-7
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: FGWPKXSVSDUYAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  惕格酸 在 正丁基锂 、 氯化亚砜 、 copper (I) iodide 、 三氯化铁 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 34.83h， 生成 2,3-dimethyl-5-methylene-4-oxo-cyclopent-2-enecarboxylic acid methyl ester
  参考文献：
  名称：

  快速合成（+/-）-desepoxy-4,5-didehydromethylenomycin a甲酯

  摘要：

  六步合成了脱环氧-4,5-didehydromethylenomycin A的外消旋甲酯的全合成，从甲烷膦酸二乙酯开始，总收率为31％。关键步骤包括二烯酮7的纳扎罗夫环化反应，产生α-磷酰基环戊烯酮8，后者的霍纳-维蒂希反应用于引入环外亚甲基部分。

  DOI：

  10.1021/ol005742b

文献信息

• Photochemistry of alkylated 4,4-dimethoxy-2,5-cyclohexadienones in methanol. Synthesis of methyl ester of (±)-desepoxy-2,5-didehydromethylenomycin A
  作者：Fang-Tsao Hong、Kung-Shing Lee、Chun-Chen Liao

  DOI：10.1016/0040-4039(92)88165-2

  日期：1992.4

  Alkylated 4,4-dimethoxy-2,5-cyclohexadienones were irradiated in methanol to give 2-cyclopentenones derivatives in fair yields. Methyl ester of (±)-desepoxy-2,5-didehydromethylenomycin A was prepared from 2,3-dimethylhydroquinone monomethyl ether in four steps and 36% overall yield using this photochemical reaction as a key step.

  在甲醇中辐照烷基化的4,4-二甲氧基-2,5-环己二酮，以合理的收率得到2-环戊烯酮衍生物。使用该光化学反应作为关键步骤，由2,3-二甲基对苯二酚单甲醚分四个步骤，以36％的总收率制备（±）-脱环氧-2,5-二氢甲基苯菌灵A的甲酯。
• Formal Syntheses of (±)-Methylenomycins A and B
  作者：Fang-Tsao Hong、Kung-Shing Lee、Chun-Chen Liao

  DOI：10.1002/jccs.200000008

  日期：2000.2

  The syn the ses of methyl es ter of ( ±)-desepoxy-4,5-didehydromethylenomycin A ( 4) and 2,3-dimethyl-5methoxycarbonyl-2-cyclopentenone ( 5) were ac com plished from a com mon start ing ma te rial, 2,3-dimethyl4-methoxyphenol ( 8), in only four and two steps in 35% and 53% over all yields, re spec tively. Pho to chem i cal re ar range ments of masked p-benzoquinones in meth a nol are the key steps

  (±)-去环氧-4,5-二去氢亚甲基霉素A(4)和2,3-二甲基-5甲氧羰基-2-环戊烯酮(5)的甲酯的合成是由共同的起始材料完成的。材料，2,3-二甲基4-甲氧基苯酚(8)，仅经过四步和两步，总产率分别为35%和53%。甲基中掩蔽的对苯醌的化学反应是关键步骤。
• Total synthesis of (±)-desepoxy-4,5-didehybromethylenomycin A
  作者：Diane Boschelli、Robert M. Scarborough、Amos B. Smith

  DOI：10.1016/0040-4039(81)80029-9

  日期：1981.1

  The total synthesis of (±)-desepoxy-4,5-didehydromethylenomycin A employing a retrolactonization strategy has been achieved.

  已经实现了采用逆内酯化策略的（±）-脱环氧-4,5-二氢甲基松香霉素A的全合成。
• Synthesis of deepoxy-4,5-didehydromethylenomycin a and methylenomycin a methyl esters
  作者：C. Mahidol、C. Thebtaranonth、Y. Thebtaranonth、C. Yenjai

  DOI：10.1016/s0040-4039(01)80677-8

  日期：1989.1

  [±]-Deepoxy-4,5-didehydromethylenomycin A methyl ester 8 and [±]-methylenomycin A methyl ester 9 are synthesized from anthracene adduct 2 via a common intermediate 13. Flash vacuum pyrolysis of adduct 13 gives 8, while stereospecific epoxidation of 13 followed by pyrolysis yields 9.

  [±] -Deepoxy-4,5-didehydromethylenomycin A甲酯8和[±] -methylenomycin A甲酯9由蒽加合物2经由共同的中间体13合成。加合物13的闪蒸真空热解得到8，而13的立体有择环氧化反应随后热解产生9。
• Cyclopentannelation Reaction for Rapid Assembly of Multifunctional Products. (d,l)-Desepoxymethylenomycin a Methyl Ester
  作者：Marcus A. Tius、Chun-Kiu Kwok、Xue-Qin Gu、Chengwen Zhao

  DOI：10.1080/00397919408011309

  日期：1994.3

  The scope of the alkoxyallene cationic cyclopentannelation reaction has been examined. Non-hydrogen substituents at both C4 and C5 were required for synthetically useful yields. Whereas the cyclization appeared to be subject to steric constraints, it was relatively insensitive to electronic effects. An efficient synthesis of (d,l)- , desepoxymethylenomycin A methyl ester has been described.