(5S,6S)-6-(benzo[d][1,3]dioxol-5-yl)-5-vinyltetrahydro-2H-pyran-2-one | 1346159-02-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (5S,6S)-6-(benzo[d][1,3]dioxol-5-yl)-5-vinyltetrahydro-2H-pyran-2-one
• 英文别名: (5S,6S)-6-(1,3-benzodioxol-5-yl)-5-ethenyloxan-2-one
• CAS: 1346159-02-1
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: UMCAIRKIHWXOFO-OTYXRUKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  dimethyl 2-(2-(benzo[d][1,3]dioxol-5-yl(hydroxy)methyl)but-3-en-1-yl)malonate 在 sodium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 18.0h， 生成 (5S,6S)-6-(benzo[d][1,3]dioxol-5-yl)-5-vinyltetrahydro-2H-pyran-2-one 、 6-(benzo[d][1,3]dioxol-5-yl)-5-vinyltetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  Polarity Inversion of Donor–Acceptor Cyclopropanes: Disubstituted δ-Lactones via Enantioselective Iridium Catalysis

  摘要：

  The coupling of carbonyl electrophiles at the donor position of donor acceptor cyclopropanes is described, representing an inversion of polarity with respect to conventional reactivity modes displayed by these reagents. Specifically, upon exposure of donor-acceptor cyclopropanes to alcohols in the presence of a cyclometalated iridium catalyst modified by (S)-BINAP, catalytic C-C coupling occurs, providing enantiomerically enriched products of carbonyl allylation. Identical products are obtained upon isopropanol-mediated transfer hydrogenation of donor acceptor cyclopropanes in the presence of aldehydes. The reaction products are directly transformed to cis-4, 5-disubstituted delta-lactones.

  DOI：

  10.1021/ja2090993