3-trideuteromethoxyphenol | 104714-88-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-trideuteromethoxyphenol
• 英文别名: resorcinol O-mono-trideuteriomethyl ether；m-methoxyphenol-d3；3-Methoxy (D3)phenol；3-(trideuteriomethoxy)phenol
• CAS: 104714-88-7
• 化学式: C₇H₈O₂
• 分子量: 127.115
• InChiKey: ASHGTJPOSUFTGB-FIBGUPNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-trideuteromethoxyphenol 在 palladium on activated charcoal 氢氧化钾 、 甲酸 、 硝酸 、 丙酸 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Elucidating the Transformation Pattern of the Cereal Allelochemical 6-Methoxy-2-benzoxazolinone (MBOA) and the Trideuteriomethoxy Analogue [D₃]-MBOA in Soil

  摘要：

  To deduce the structure of the large array of compounds arising from the transformation pathway of 6-methoxybenzoxazolin-2-one (MBOA), the combination of isotopic substitution and liquid chromatography analysis with mass spectrometry detection was used as a powerful tool. MBOA is formed in soil when the cereal allelochemical 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) is exuded from plant material to soil. Degradation experiments were performed in concentrations of 400 mu g of benzoxazolinone/g of soil for MBOA and its isotopomer 6-trideuteriomethoxybenzoxazolin-2-one ([D-3]-MBOA). Previously identified metabolites 2-amino-7-methoxyphenoxazin-3-one (AMPO) and 2-acetylamino-7-methoxyphenoxazin-3-one (AAMPO) were detected. Furthermore, several novel compounds were detected and provisionally characterized. The environmental impact of these compounds and their long-range effects are yet to be discovered. This is imperative due to the enhanced interest in exploiting the allelopathic properties of cereals as a means of reducing the use of synthetic pesticides.

  DOI：

  10.1021/jf0509052
• 作为产物：
  描述：

  D3-对甲苯磺酰甲酯 、 间苯二酚 在 sodium methylate 作用下， 生成 3-trideuteromethoxyphenol
  参考文献：
  名称：

  一种新型的异常Reimer-tiemann反应

  摘要：

  在常规Reimer-Tiemann反应条件下，用氯仿和氢氧化钾水溶液处理1、2、3、4、4a，9b-六氢-3、8-二羟基-7-甲氧基-9b-（2'-甲氧基乙基）二苯并呋喃在用甲醛取代7-甲氧基的过程中。通过检查相应的7-三氟甲氧基甲氧基化合物的行为，已经为这种新颖的置换选择了其他途径。二氯卡宾在位置7而不是在未取代的位置9的进攻表明是由于后者位点的空间负担。

  DOI：

  10.1016/s0040-4020(01)82364-4

文献信息

• A new type of abnormal reimer-tiemann reaction
  作者：C.W. Bird、A.L. Bronw、C.C. Chan

  DOI：10.1016/s0040-4020(01)82364-4

  日期：1985.1

  The treatment of l, 2, 3, 4, 4a, 9b-hexahydro-3, 8-dihydroxy-7-methoxy-9b-(2'-methoxyethyl)dibenzofuran with chloroform and aqueous potassium hydroxide under conventional Reimer-Tiemann reaction conditions resulted in the replacement of the 7-methoxyl group by a carbaldehyde one. A choice between alternative pathways for this novel displacement has been facilitated by examination of the behaviour of

  在常规Reimer-Tiemann反应条件下，用氯仿和氢氧化钾水溶液处理1、2、3、4、4a，9b-六氢-3、8-二羟基-7-甲氧基-9b-（2'-甲氧基乙基）二苯并呋喃在用甲醛取代7-甲氧基的过程中。通过检查相应的7-三氟甲氧基甲氧基化合物的行为，已经为这种新颖的置换选择了其他途径。二氯卡宾在位置7而不是在未取代的位置9的进攻表明是由于后者位点的空间负担。
• BIRD, C. W.;BROWN, A. L.;CHAN, C. C., TETRAHEDRON, 1985, 41, N 20, 4685-4690
  作者：BIRD, C. W.、BROWN, A. L.、CHAN, C. C.

  DOI：——

  日期：——
• Elucidating the Transformation Pattern of the Cereal Allelochemical 6-Methoxy-2-benzoxazolinone (MBOA) and the Trideuteriomethoxy Analogue [D₃]-MBOA in Soil
  作者：Thomas Etzerodt、Susan T. Nielsen、Anne G. Mortensen、Carsten Christophersen、Inge S. Fomsgaard

  DOI：10.1021/jf0509052

  日期：2006.2.1

  To deduce the structure of the large array of compounds arising from the transformation pathway of 6-methoxybenzoxazolin-2-one (MBOA), the combination of isotopic substitution and liquid chromatography analysis with mass spectrometry detection was used as a powerful tool. MBOA is formed in soil when the cereal allelochemical 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) is exuded from plant material to soil. Degradation experiments were performed in concentrations of 400 mu g of benzoxazolinone/g of soil for MBOA and its isotopomer 6-trideuteriomethoxybenzoxazolin-2-one ([D-3]-MBOA). Previously identified metabolites 2-amino-7-methoxyphenoxazin-3-one (AMPO) and 2-acetylamino-7-methoxyphenoxazin-3-one (AAMPO) were detected. Furthermore, several novel compounds were detected and provisionally characterized. The environmental impact of these compounds and their long-range effects are yet to be discovered. This is imperative due to the enhanced interest in exploiting the allelopathic properties of cereals as a means of reducing the use of synthetic pesticides.