(Z)-2-(3-phenylprop-2-ynylidene)-1,6-dioxaspiro[4.5]dec-3-ene | 784193-74-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-2-(3-phenylprop-2-ynylidene)-1,6-dioxaspiro[4.5]dec-3-ene
• 英文别名: (2Z)-2-(3-phenylprop-2-ynylidene)-1,6-dioxaspiro[4.5]dec-3-ene；(2Z)-2-(3-phenylprop-2-ynylidene)-1,10-dioxaspiro[4.5]dec-3-ene
• CAS: 784193-74-4
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: IBZXBWRYXHAWIM-YBEGLDIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-2-(3-phenylprop-2-ynylidene)-1,6-dioxaspiro[4.5]dec-3-ene 在 camphor-10-sulfonic acid 作用下， 以 氘代氯仿 为溶剂， 生成 (E)-2-(3-phenylprop-2-ynylidene)-1,6-dioxaspiro[4.5]dec-3-ene
  参考文献：
  名称：

  通过呋喃衍生物的氧化活化合成螺缩醛烯醇醚。

  摘要：

  通过电子转移激活呋喃与炔基取代基（R = Ph，MeC [三键] C-）的自由基稳定作用相结合，实现了位点选择性阳离子的形成。束缚的羟基充当该位点选择性的探针，以产生存在于蒿和菊花物种中的螺环天然产物中的环系统。相对于四氢吡喃基环氧，顺-二羟基化以高的抗立体选择性进行。

  DOI：

  10.1021/ol802138t
• 作为产物：
  描述：

  acetic acid 4-[5-(1-hydroxy-3-phenylprop-2-ynyl)furan-2-yl]butyl ester 在 potassium carbonate 、 copper(II) sulfate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 14.0h， 生成 (Z)-2-(3-phenylprop-2-ynylidene)-1,6-dioxaspiro[4.5]dec-3-ene
  参考文献：
  名称：

  Synthesis and Antifeeding Activities of Tonghaosu Analogues

  摘要：

  Tonghaosu (1), a lead for a botanical antifeedant, and its 22 analogues were synthesized according to a previously reported concise and straightforward procedure. The structures of all new compounds were confirmed by NMR, IR, MS, and HREIMS or elemental analysis. Their insect antifeedant activities against the large white butterfly (Pieris brassicae L.) were examined, and six analogues (Z- and E-6h and Z-isomers of 6i-I), which contain 1,3-diyn or 3,4-methylenedioxyphenyl acetylene group, showed considerable antifeedant activity. Interestingly, Zisomers of 6i-k are much more active than their corresponding E-isomers.

  DOI：

  10.1021/jf049479v

文献信息

• Synthesis and Antifeeding Activities of Tonghaosu Analogues
  作者：Li Chen、Han-Hong Xu、Biao-Lin Yin、Chun Xiao、Tai-Shan Hu、Yu-Lin Wu

  DOI：10.1021/jf049479v

  日期：2004.11.1

  Tonghaosu (1), a lead for a botanical antifeedant, and its 22 analogues were synthesized according to a previously reported concise and straightforward procedure. The structures of all new compounds were confirmed by NMR, IR, MS, and HREIMS or elemental analysis. Their insect antifeedant activities against the large white butterfly (Pieris brassicae L.) were examined, and six analogues (Z- and E-6h and Z-isomers of 6i-I), which contain 1,3-diyn or 3,4-methylenedioxyphenyl acetylene group, showed considerable antifeedant activity. Interestingly, Zisomers of 6i-k are much more active than their corresponding E-isomers.
• Synthesis of Spiroacetal Enol Ethers by Oxidative Activation of Furan Derivatives
  作者：Jeremy Robertson、Sébastien Naud

  DOI：10.1021/ol802138t

  日期：2008.12.4

  Activation of furan by electron transfer combines with the radical stabilizing effect of the alkynyl substituent (R = Ph, MeC[triple bond]C-) to achieve site-selective cation formation. A tethered hydroxy group acts as a probe of this site-selectivity to produce the ring system present in spirocyclic natural products found in Artemisia and Chrysanthemum species. cis-Dihydroxylation proceeds with high

  通过电子转移激活呋喃与炔基取代基（R = Ph，MeC [三键] C-）的自由基稳定作用相结合，实现了位点选择性阳离子的形成。束缚的羟基充当该位点选择性的探针，以产生存在于蒿和菊花物种中的螺环天然产物中的环系统。相对于四氢吡喃基环氧，顺-二羟基化以高的抗立体选择性进行。