(S,Z)-2-butylidene-1-(3,4-dihydro-2H-pyran-6-yl)-3-(2-oxo-4-phenyloxazolidin-3-yl)propane-1,3-dione | 1252612-16-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S,Z)-2-butylidene-1-(3,4-dihydro-2H-pyran-6-yl)-3-(2-oxo-4-phenyloxazolidin-3-yl)propane-1,3-dione
• CAS: 1252612-16-0
• 化学式: C₂₁H₂₃NO₅
• 分子量: 369.417
• InChiKey: VGTINBGOOIFWOI-ZFOVBUMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S,Z)-2-butylidene-1-(3,4-dihydro-2H-pyran-6-yl)-3-(2-oxo-4-phenyloxazolidin-3-yl)propane-1,3-dione 在 甲烷磺酸 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到(S)-3-[(5S,6S)-7-oxo-5-propyl-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-6-carbonyl]-4-phenyloxazolidin-2-one
  参考文献：
  名称：

  A Reductive-Coupling plus Nazarov Cyclization Sequence in the Asymmetric Synthesis of Five-Membered Carbocycles

  摘要：

  Palladium-mediated hydrostannylation of alkynoyl compounds is combined with Stille-Scott cross-coupling (reductive-coupling) to give one-pot access to divinyl and aryl vinyl ketones, which undergo Nazarov cyclization to give cyclopentenones upon treatment with acid. This reaction sequence has been studied with a variety of different substitution patterns, including the use of oxazolidinone auxiliaries to achieve torquoselectivity in the Nazarov cyclization. Through a combination of good yields and moderate to good levels of stereochemical induction, this approach affords efficient, convergent, and asymmetric access to a variety of different cyclopentanoid systems.

  DOI：

  10.1021/jo100736p
• 作为产物：
  描述：

  (S)-3-hex-2-ynoyl-4-phenyloxazolidin-2-one 、 3,4-dihydro-2H-pyran-6-carbonyl chloride 在 四(三苯基膦)钯 、 三正丁基氢锡 、 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到(S,Z)-2-butylidene-1-(3,4-dihydro-2H-pyran-6-yl)-3-(2-oxo-4-phenyloxazolidin-3-yl)propane-1,3-dione
  参考文献：
  名称：

  A Reductive-Coupling plus Nazarov Cyclization Sequence in the Asymmetric Synthesis of Five-Membered Carbocycles

  摘要：

  Palladium-mediated hydrostannylation of alkynoyl compounds is combined with Stille-Scott cross-coupling (reductive-coupling) to give one-pot access to divinyl and aryl vinyl ketones, which undergo Nazarov cyclization to give cyclopentenones upon treatment with acid. This reaction sequence has been studied with a variety of different substitution patterns, including the use of oxazolidinone auxiliaries to achieve torquoselectivity in the Nazarov cyclization. Through a combination of good yields and moderate to good levels of stereochemical induction, this approach affords efficient, convergent, and asymmetric access to a variety of different cyclopentanoid systems.

  DOI：

  10.1021/jo100736p