(+)-9-hydroxy-5-nonanolide | 110720-01-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (+)-9-hydroxy-5-nonanolide
• 英文别名: (6R)-6-(4-hydroxybutyl)oxan-2-one
• CAS: 110720-01-9
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: IZTXPBCYVLHADI-MRVPVSSYSA-N

物化性质

• 沸点：
  332.1±15.0 °C(Predicted)
• 密度：
  1.062±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-9-hydroxy-5-nonanolide 在 palladium on activated charcoal 草酰氯 、 potassium tert-butylate 、 氢气 、 二甲基亚砜 作用下， 以 乙醚 为溶剂， -60.0~25.0 ℃ 、101.33 kPa 条件下， 反应 3.5h， 生成 (+)-(6R)-四氢-6-十一烷基-2H-吡喃-2-酮
  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：

  5-Acetyloxynonanedioic acid 在 吡啶 、 锂硼氢 、 氯化亚砜 、 水 、 hydroxide 、 对甲苯磺酸 、 三乙胺 、 三氟乙酸酐 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (+)-9-hydroxy-5-nonanolide
  参考文献：
  名称：

  Novel asymmetric synthesis of optically active .delta.- and .gamma.-lactones using a C2-chiral auxiliary

  摘要：

  DOI：

  10.1021/ja00257a046

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：——
• SAKAMOTO, AKIO;YAMAMOTO, YUKIO;ODA, JUNICHI, J. AMER. CHEM. SOC., 109,(1987) N 23, 7188-7189
  作者：SAKAMOTO, AKIO、YAMAMOTO, YUKIO、ODA, JUNICHI

  DOI：——

  日期：——