3-((1R,2R)-2-(12-methyltridecyl)cyclopropyl)propanoic acid | 1414963-09-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-((1R,2R)-2-(12-methyltridecyl)cyclopropyl)propanoic acid
• 英文别名: 3-[(1R,2R)-2-(12-methyltridecyl)cyclopropyl]propanoic acid
• CAS: 1414963-09-9
• 化学式: C₂₀H₃₈O₂
• 分子量: 310.521
• InChiKey: MLUVGOHIKYMWQZ-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  10-溴-1-癸醇 在 咪唑 、 dilithium tetrachlorocuprate 、 SiO₂-supported NaIO₄ 、 碘 、 sodium acetate 、 sodium hexamethyldisilazane 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 magnesium 、 对甲苯磺酰肼 、 三苯基膦 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 18.17h， 生成 3-((1R,2R)-2-(12-methyltridecyl)cyclopropyl)propanoic acid
  参考文献：
  名称：

  The first asymmetric total syntheses of 3((1R,2R)- and 3((1S,2R)-2-(12-methyltridecyl)cyclopropyl)propanoic acid

  摘要：

  The first efficient total syntheses of 3((1 R,2R)- and 3((1S,2R)-2-(12-methyltridecyl)cyclopropyl)propanoic acid have been achieved following a chelation controlled modified Simmon-Smith cyclopropanation, Wittig reaction, Horner-Wadsworth-Emmons olefination, and p-toluenesulfonyl hydrazide catalyzed hydrogenation as key reactions in good overall yield. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.133

文献信息

• The first total synthesis of the (±)-17-methyl-trans-4,5-methyleneoctadecanoic acid and related analogs with antileishmanial activity
  作者：Néstor M. Carballeira、Nashbly Montano、Rosa M. Reguera、Rafael Balaña-Fouce

  DOI：10.1016/j.tetlet.2010.09.083

  日期：2010.11

  The first total synthesis of the marine cyclopropane fatty acid (±)-17-methyl-trans-4,5-methyleneoctadecanoic acid was accomplished in eight steps and in 9.1% overall yield starting from 1-bromo-12-methyltridecane. The cis analog (±)-17-methyl-cis-4,5-methyleneoctadecanoic acid was also synthesized but in seven steps and in 16.4% overall yield. With the two isomeric cyclopropane fatty acids at hand it

  海洋环丙烷脂肪酸 (±)-17-甲基-反式-4,5-亚甲基十八烷酸的首次全合成分八步完成，从 1-溴-12-甲基十三烷开始，总产率为 9.1%。的顺式类似物（±）-17-甲基-顺式-4,5- methyleneoctadecanoic酸还合成但在七个步骤和在16.4％的总收率。使用手头的两种异构环丙烷脂肪酸，可以通过相应甲酯的气相色谱共洗脱来明确证实天然存在的脂肪酸的反式相对构型。的顺式异构体为细胞毒性杜氏利什曼原虫前鞭毛体的IC 50 300.2 ± 4.2 μM。
• The first asymmetric total syntheses of 3((1R,2R)- and 3((1S,2R)-2-(12-methyltridecyl)cyclopropyl)propanoic acid
  作者：Debendra K. Mohapatra、Nagesh Guguloth、J.S. Yadav

  DOI：10.1016/j.tetlet.2012.09.133

  日期：2012.12

  The first efficient total syntheses of 3((1 R,2R)- and 3((1S,2R)-2-(12-methyltridecyl)cyclopropyl)propanoic acid have been achieved following a chelation controlled modified Simmon-Smith cyclopropanation, Wittig reaction, Horner-Wadsworth-Emmons olefination, and p-toluenesulfonyl hydrazide catalyzed hydrogenation as key reactions in good overall yield. (C) 2012 Elsevier Ltd. All rights reserved.