(4S,5R)-2-Hexa-2,4-diyn-(E)-ylidene-1,6-dioxa-spiro[4.5]decan-4-ol | 219559-66-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4S,5R)-2-Hexa-2,4-diyn-(E)-ylidene-1,6-dioxa-spiro[4.5]decan-4-ol
• CAS: 219559-66-7
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: NOOKWDVEEHAOTC-AMNUONFKSA-N

反应信息

• 作为反应物：
  描述：

  (4S,5R)-2-Hexa-2,4-diyn-(E)-ylidene-1,6-dioxa-spiro[4.5]decan-4-ol 在 吡啶 、 potassium tert-butylate 作用下， 反应 27.0h， 生成 (2Z,5R)-2-(2′,4′-hexadiynylidene)-1,6-dioxaspiro[4.5]dec-3-ene
  参考文献：
  名称：

  Isolation and Identification of Acetylenic Spiroketal Enol Ethers from Artemisia lactiflora as Inhibitors of Superoxide Generation Induced by a Tumor Promoter in Differentiated HL-60 Cells

  摘要：

  Six acetylenic compounds were isolated from the leaves of Artemisia lactiflora (Compositae), an edible plant of Thailand. Four of them were identified as the stereoisomers of 3,4-epoxy-2-(2,4-hexadiynylidene)-1,6-dioxaspiro[4.5]decane and its derivatives, whose planar structures have already been reported. The other two were identified as novel chlorohydrin derivatives of the corresponding diacetylene spiroketal enol ethers. The inhibitory effects of the polyacetylenes isolated in the present study together with genistein on TPA-induced O-2(-) generation were examined. It was revealed that an acyloxyl group at the C-2 position enhanced-the inhibitory effect, while the absolute configurations at C-5, -6, and -7 were not important. While polyacetylenes are known to possess several biological roles in various ecosystems, we first found inhibitory effects of the diacetylenes on TPA-induced O-2(-) generation in differentiated HL-60 cells.

  DOI：

  10.1021/jf980521u
• 作为产物：
  描述：

  (1S,2R,4E,5R)-4-hexa-2,4-diynylidenespiro[3,6-dioxabicyclo[3.1.0]hexane-2,2'-oxane] 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以58%的产率得到(4S,5R)-2-Hexa-2,4-diyn-(E)-ylidene-1,6-dioxa-spiro[4.5]decan-4-ol
  参考文献：
  名称：

  Isolation and Identification of Acetylenic Spiroketal Enol Ethers from Artemisia lactiflora as Inhibitors of Superoxide Generation Induced by a Tumor Promoter in Differentiated HL-60 Cells

  摘要：

  Six acetylenic compounds were isolated from the leaves of Artemisia lactiflora (Compositae), an edible plant of Thailand. Four of them were identified as the stereoisomers of 3,4-epoxy-2-(2,4-hexadiynylidene)-1,6-dioxaspiro[4.5]decane and its derivatives, whose planar structures have already been reported. The other two were identified as novel chlorohydrin derivatives of the corresponding diacetylene spiroketal enol ethers. The inhibitory effects of the polyacetylenes isolated in the present study together with genistein on TPA-induced O-2(-) generation were examined. It was revealed that an acyloxyl group at the C-2 position enhanced-the inhibitory effect, while the absolute configurations at C-5, -6, and -7 were not important. While polyacetylenes are known to possess several biological roles in various ecosystems, we first found inhibitory effects of the diacetylenes on TPA-induced O-2(-) generation in differentiated HL-60 cells.

  DOI：

  10.1021/jf980521u