5-methyl-4-O-methyl tetramate | 109826-89-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 5-methyl-4-O-methyl tetramate
• 英文别名: 4-methoxy-5-methyl-3-pyrrolin-2-one；4-Methoxy-5-methyl-1H-pyrrol-2(5H)-one；3-methoxy-2-methyl-1,2-dihydropyrrol-5-one
• CAS: 109826-89-3
• 化学式: C₆H₉NO₂
• mdl: MFCD12923627
• 分子量: 127.143
• InChiKey: YJHSJKBMTSQOII-UHFFFAOYSA-N

物化性质

• 沸点：
  323.1±42.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methyl-4-O-methyl tetramate 、 在 sodium hydride 作用下， 生成 、 (2'R,3'R,5S)-1-(3'-((tert-butyldimethylsilyl)oxy)-2'-methyl-8',8',9',9'-tetrachlorodecanoyl)-4-methoxy-5-methyl-3-pyrrolin-2-one
  参考文献：
  名称：

  Mirabimide E, an Unusual N-Acylpyrrolinone from the Blue-Green Alga Scytonema mirabile: Structure Determination and Synthesis

  摘要：

  Mirabimide E, a solid tumor selective cytotoxin from the terrestrial blue-green alga Scytonema mirabile UH strain BY-8-1, possesses an unprecedented tetrachlorinated ethylene group and has been identified as (5S,2'R,3'R)-N- (anti-8/,8',9',9'-tetrachloro-3'-(carbamoyloxy)-2'-methyldecanoyl)-4-methoxy-5-methyl-3-pyrrolin-2-one. The total structure, including absolute stereochemistry, of this novel N-acylpyrrolinone was concluded from a combination of spectral and chemical studies, including stereoselective syntheses of three degradation products, viz. methyl (2R,3R)-anti-8,8,9,9-tetrachloro-3-hydroxy-2-methyldecanoate, (5R,6R)-trans-5-methyl-6-(5,5',6,6'-tetrachloroheptyl-1-oxa- 3-azacyclohexane-2,4-dione, and (5S)-4-methoxy-5-methyl-3-pyrrolin-2-one and the total synthesis of mirabimide E itself. The influence of the carbamate ester group on the chemical degradation and synthesis of mirabimide E is described.

  DOI：

  10.1021/ja00097a019
• 作为产物：
  描述：

  4-溴-3-甲氧基-2-丁烯酸甲酯 在 ammonium hydroxide 、 氢氟酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 12.0h， 生成 5-methyl-4-O-methyl tetramate
  参考文献：
  名称：

  Synthesis of 5-substituted 4--methyl tetramates

  摘要：

  DOI：

  10.1016/s0040-4039(00)85192-8

文献信息

• Jones, Raymond C. F.; Patience, Jacqueline M., Journal of the Chemical Society. Perkin transactions I, 1990, # 8, p. 2350 - 2351
  作者：Jones, Raymond C. F.、Patience, Jacqueline M.

  DOI：——

  日期：——
• JONES, RAYMOND C. F.;PATIENCE, JACQUELINE M., J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 2350-2351
  作者：JONES, RAYMOND C. F.、PATIENCE, JACQUELINE M.

  DOI：——

  日期：——
• JONES R. C. F.; BATES A. D., TETRAHEDRON LETT., 27,(1986) N 43, 5285-5288
  作者：JONES R. C. F.、 BATES A. D.

  DOI：——

  日期：——
• Mirabimide E, an Unusual N-Acylpyrrolinone from the Blue-Green Alga Scytonema mirabile: Structure Determination and Synthesis
  作者：Seunguk Paik、Shmuel Carmeli、Jean Cullingham、Richard E. Moore、Gregory M. L. Patterson、Marcus A. Tius

  DOI：10.1021/ja00097a019

  日期：1994.9

  Mirabimide E, a solid tumor selective cytotoxin from the terrestrial blue-green alga Scytonema mirabile UH strain BY-8-1, possesses an unprecedented tetrachlorinated ethylene group and has been identified as (5S,2'R,3'R)-N- (anti-8/,8',9',9'-tetrachloro-3'-(carbamoyloxy)-2'-methyldecanoyl)-4-methoxy-5-methyl-3-pyrrolin-2-one. The total structure, including absolute stereochemistry, of this novel N-acylpyrrolinone was concluded from a combination of spectral and chemical studies, including stereoselective syntheses of three degradation products, viz. methyl (2R,3R)-anti-8,8,9,9-tetrachloro-3-hydroxy-2-methyldecanoate, (5R,6R)-trans-5-methyl-6-(5,5',6,6'-tetrachloroheptyl-1-oxa- 3-azacyclohexane-2,4-dione, and (5S)-4-methoxy-5-methyl-3-pyrrolin-2-one and the total synthesis of mirabimide E itself. The influence of the carbamate ester group on the chemical degradation and synthesis of mirabimide E is described.
• Synthesis of 5-substituted 4--methyl tetramates
  作者：Raymond C.F Jones、Andrew D Bates

  DOI：10.1016/s0040-4039(00)85192-8

  日期：1986.1