(4R,5R)-2-Hexa-2,4-diyn-(E)-ylidene-1,6-dioxa-spiro[4.5]decan-4-ol | 116258-27-6

• 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: (4R,5R)-2-Hexa-2,4-diyn-(E)-ylidene-1,6-dioxa-spiro[4.5]decan-4-ol
• 英文别名: (2E,4R,5R)-2-hexa-2,4-diynylidene-1,10-dioxaspiro[4.5]decan-4-ol
• CAS: 116258-27-6
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: NOOKWDVEEHAOTC-DXIMFJFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,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：

  (-)-(2E,3S,4R,5R)-3,4-epoxy-2-(2,4-hexadiynylidene)-1,6-dioxaspiro[4.5]decane 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.17h， 以15 mg的产率得到(4R,5R)-2-Hexa-2,4-diyn-(E)-ylidene-1,6-dioxa-spiro[4.5]decan-4-ol
  参考文献：
  名称：

  两种天然炔属螺环酮烯醇醚环氧化物的相对和绝对构型

  摘要：

  雪蒿的地下部分提供了一个新的C 14炔六环螺环酮烯醇醚环氧化物。一个密切相关的非对映体化合物先前已经分离，但是，环氧环（的相对构型反或顺式与参考氧气）不能成立。通过1 H-镧系元素引起的位移和13 C NMR数据的比较，阐明了反Syn对的相对立体化学。使用Horeau的方法通过相应的甲醇推导出绝对构型。结果用CD测量和平衡实验证实抗⇌顺式对。

  DOI：

  10.1016/s0040-4020(01)85117-6

文献信息

• BIRNECKER, WALTER;WALLNOFER, BRUNO;HOFER, OTMAR;GREGER, HARALD, TETRAHEDRON, 44,(1988) N 1, 267-276
  作者：BIRNECKER, WALTER、WALLNOFER, BRUNO、HOFER, OTMAR、GREGER, HARALD

  DOI：——

  日期：——