4-(acetoxymethyl)heptanedioic acid | 131702-85-7

• 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: 4-(acetoxymethyl)heptanedioic acid
• 英文别名: 4-(acetyloxymethyl)heptanedioic acid
• CAS: 131702-85-7
• 化学式: C₁₀H₁₆O₆
• 分子量: 232.233
• InChiKey: KMWXZKGDXPCKSD-UHFFFAOYSA-N

物化性质

• 沸点：
  435.0±40.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  100.9
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(acetoxymethyl)heptanedioic acid 在 氯化亚砜 作用下， 以99%的产率得到4-(acetoxymethyl)heptanedioyl dichloride
  参考文献：
  名称：

  Asymmetric synthesis of 5- and 6-membered lactones from cyclic substrates bearing a C2-chiral auxiliary

  摘要：

  Optically active lactones were synthesized by a novel asymmetric synthesis in which enantiotopic groups remote from a prochiral center were effectively discriminated. The cyclic diamide alcohols bearing a C2-chiral auxiliary, (+)-[1,1'-binaphthyl]-2,2'-diamine (4), were designed and prepared such that the hydroxyl group should attack preferentially at one of the two carbonyl groups. By the catalytic action of trifluoroacetic acid, the substrates 6a,b and 19 were smoothly converted to the lactones 7a (71% de), 7b (97% de), and 20 (> 99% de), the configurations of which were determined to be R, S, and R, respectively. A naturally occurring pheromone, (R)-(+)-5-hexadecanolide (13), was synthesized optically pure from 7b. Transition-state models for the present asymmetric lactonization were constructed according to the stereoelectronic theory proposed by Deslongchamps. The stability of the models was assessed by MM2 calculation, and the direction of asymmetric induction thus calculated coincided with the experimental results.

  DOI：

  10.1021/jo00003a038
• 作为产物：
  描述：

  4-酮庚二酸 在 吡啶 、 9-borabicyclo[3.3.1]nonane dimer 、 甲酸 、 硫酸 、 potassium tert-butylate 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 171.0h， 生成 4-(acetoxymethyl)heptanedioic acid
  参考文献：
  名称：

  Asymmetric synthesis of 5- and 6-membered lactones from cyclic substrates bearing a C2-chiral auxiliary

  摘要：

  Optically active lactones were synthesized by a novel asymmetric synthesis in which enantiotopic groups remote from a prochiral center were effectively discriminated. The cyclic diamide alcohols bearing a C2-chiral auxiliary, (+)-[1,1'-binaphthyl]-2,2'-diamine (4), were designed and prepared such that the hydroxyl group should attack preferentially at one of the two carbonyl groups. By the catalytic action of trifluoroacetic acid, the substrates 6a,b and 19 were smoothly converted to the lactones 7a (71% de), 7b (97% de), and 20 (> 99% de), the configurations of which were determined to be R, S, and R, respectively. A naturally occurring pheromone, (R)-(+)-5-hexadecanolide (13), was synthesized optically pure from 7b. Transition-state models for the present asymmetric lactonization were constructed according to the stereoelectronic theory proposed by Deslongchamps. The stability of the models was assessed by MM2 calculation, and the direction of asymmetric induction thus calculated coincided with the experimental results.

  DOI：

  10.1021/jo00003a038

文献信息

• YAMAMOTO, YUKIO;SAKAMOTO, AKIO;NISHIOKA, TAKAAKI;ODA, JUNICHI;FUKAZAWA, Y+, J. ORG. CHEM., 56,(1991) N, C. 1112-1119
  作者：YAMAMOTO, YUKIO、SAKAMOTO, AKIO、NISHIOKA, TAKAAKI、ODA, JUNICHI、FUKAZAWA, Y+

  DOI：——

  日期：——