(2R,3R)-8,8,9,9-tetrachloro-3-hydroxy-2-methyldecanoic acid | 159614-53-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (2R,3R)-8,8,9,9-tetrachloro-3-hydroxy-2-methyldecanoic acid
• CAS: 159614-53-6
• 化学式: C₁₁H₁₈Cl₄O₃
• 分子量: 340.074
• InChiKey: OXVXANUAZBRARD-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R)-8,8,9,9-tetrachloro-3-hydroxy-2-methyldecanoic acid 在 咪唑 、 lithium hydroxide 、 氢氟酸 、 双氧水 、 silica gel 、 sodium hydride 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 氘代氯仿 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 61.5h， 生成
  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：

  2-庚炔-1-醇 在 sodium hydroxide 、 磺酰氯 、 potassium tert-butylate 、 四氯化钛 、 lithium 、 戴斯-马丁氧化剂 、 乙二胺 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 131.5h， 生成 (2R,3R)-8,8,9,9-tetrachloro-3-hydroxy-2-methyldecanoic acid
  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

文献信息

• 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.