(Z)-9-phenoxy-non-5-en-7-ynoic acid | 1217548-51-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-9-phenoxy-non-5-en-7-ynoic acid
• CAS: 1217548-51-0
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: KZFCAXVAZNNOOZ-UPHRSURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (Z)-9-phenoxy-non-5-en-7-ynoic acid 在 三乙烯二胺 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 syn-6-(3-bromo-4-phenoxy-buta-1,2-dienyl)-tetrahydro-pyran-2-one
  参考文献：
  名称：

  Enantioselective Bromolactonization of Conjugated (Z)-Enynes

  摘要：

  A catalytic enantioselective syn-1,4-bromolactonization of conjugated (Z)-enynes was reported. Diastereomeric ratios >20:1 and up to 99% enantiomeric excesses were observed. Di-, tri-, and tetra-substituted bromoallenes were prepared together with lactone heterocycles efficiently and stereoselectively, Preliminary investigations Suggest that the chiral catalyst may serve as a bifunctional reagent by interacting with both a carboxylic acid nucleophile and NBS electrophile.

  DOI：

  10.1021/ja100173w

文献信息

• Catalytic Enantioselective Halolactonization of Enynes and Alkenes
  作者：Wei Zhang、Na Liu、Casi M. Schienebeck、Kyle Decloux、Suqing Zheng、Jenny B. Werness、Weiping Tang

  DOI：10.1002/chem.201103809

  日期：2012.6.4

  developed for the enantioselective halolactonization of (Z)‐1,3‐enynes and 1,1‐disubstituted alkenes. In the case of 1,3‐enynes, the carboxylate nucleophile and halogen electrophile were added to the conjugated π‐system from the same face. Up to 99 % ee was achieved for the 1,4‐syn‐bromolactonization of conjugated (Z)‐1,3‐enynes. Based on the results from the enyne halolactonization, a second generation

  已开发出新的有机催化剂，用于（Z）-1,3-烯和1,1-二取代烯烃的对映选择性卤代内酯化。在1,3-烯炔的情况下，将羧酸亲核试剂和卤素亲电子试剂从同一面添加到共轭π系统中。共轭（Z）-1,3-烯炔的1,4-顺-溴内酯化可实现高达99％的 ee。基于烯炔卤代内酯化的结果，设计了第二代用于简单烯烃的催化剂。ee高达91％ 观察到1,1-二取代烯烃的氯内酯化。为烯炔和烯烃的对映选择性卤代内酯化而开发的催化剂由拴在脲基上的金鸡纳生物碱骨架组成。