(S)-(-)-2-allyl-5-pentanolide | 73746-81-3

• 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: (S)-(-)-2-allyl-5-pentanolide
• 英文别名: (S)-(-)-2-allylvalerolactone；(3S)-3-prop-2-enyloxan-2-one
• CAS: 73746-81-3
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: AKIMEVGXWODVKK-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  10.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (S)-(-)-2-allyl-5-pentanolide 在 双氧水 、 臭氧 作用下， 生成 methyl 2-(2-oxooxan-3-yl)acetate
  参考文献：
  名称：

  Asymmetric synthesis of 2-substituted butyrolactones and valerolactones

  摘要：

  DOI：

  10.1021/jo01302a009
• 作为产物：
  描述：

  5-羟基-戊腈 在 2,6-二甲基吡啶 、 盐酸 、 乙醇 、 硫酸 、 水 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 17.5h， 生成 (S)-(-)-2-allyl-5-pentanolide
  参考文献：
  名称：

  Asymmetric synthesis of 2-substituted butyrolactones and valerolactones

  摘要：

  DOI：

  10.1021/jo01302a009

文献信息

• Enantioselective and Diastereoselective Tsuji-Trost Allylic Alkylation of Lactones: An Experimental and Computational Study
  作者：Panos Meletis、Mahendra Patil、Walter Thiel、Walter Frank、Manfred Braun

  DOI：10.1002/chem.201101406

  日期：2011.9.26

  The Tsuji–Trost protocol has been successfully employed for the allylic alkylation of preformed lactone enolates. It has been demonstrated that this Pd‐catalyzed reaction can be carried out in an enantio‐ and diastereoselective manner. The use of additives, such as LiCl, was found to be crucial for reaching high levels of product selectivity. For one particular pair of reactants, density functional

  Tsuji–Trost协议已成功用于预制内酯烯醇盐的烯丙基烷基化。已经证明该钯催化的反应可以对映和非对映选择性的方式进行。发现使用添加剂（例如LiCl）对于达到高水平的产品选择性至关重要。对于一对特定的反应物，使用密度泛函理论研究亲核加成的机理。在五个途径考虑，一个（烯丙基）的Pd（BINAP）配合物和之间的反应的氯化锂，烯醇化锂加合物被预测为对C的最可能的路线C键形成。LiCl作为贵金属和烯醇化物在动力学上有利的过渡态之间的连接键起着关键作用。计算的非对映选择性比与实验观察值非常吻合。
• Asymmetric synthesis of 5- and 6-membered lactones from cyclic substrates bearing a C2-chiral auxiliary
  作者：Yukio Yamamoto、Akio Sakamoto、Takaaki Nishioka、Junichi Oda、Yoshimasa Fukazawa

  DOI：10.1021/jo00003a038

  日期：1991.2

  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.
• 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：——