2-hydroxy-3-methyl-3-butenenitrile | 22410-56-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-hydroxy-3-methyl-3-butenenitrile
• 英文别名: 2-Hydroxy-3-methylbut-3-enenitrile
• CAS: 22410-56-6
• 化学式: C₅H₇NO
• mdl: MFCD24493791
• 分子量: 97.1167
• InChiKey: WKRMIWMWBWPVQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3-methyl-3-butenenitrile 在 sodium hydroxide 、 氢溴酸 作用下， 反应 0.17h， 生成 3-Methyl-2-<(2-tetrahydropyranyl)oxy>-2-butenenitrile
  参考文献：
  名称：

  Vicinal 13C-13C coupling constants as a configurational probe: stereochemistry of the base-catalyzed double-bond shift in proacacipetalin

  摘要：

  DOI：

  10.1021/jo00154a028
• 作为产物：
  描述：

  2-甲基丙烯醛 、 氢氰酸 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到2-hydroxy-3-methyl-3-butenenitrile
  参考文献：
  名称：

  Three-carbon annelations. Regiocontrolled reactivity of trimethylsilyl- and ethoxyethyl-protected cyanohydrins. Versatile homoenolate and acyl anion equivalents

  摘要：

  DOI：

  10.1021/jo01291a005

文献信息

• Synthesis of type I and IV cyanolipids
  作者：Mugio Nishizawa、Kenji Adachi、Yuji Hayashi

  DOI：10.1039/c39840001637

  日期：——

  Type I and IV cyanolipids, members of a unique class of plant lipid, have been synthesized efficiently by means of a novel cyanoesterification of aldehydes, and fully characterzed by spectral analysis; an artifical ‘type V’ cyanolipid has also been synthesized.

  I和IV型氰脂脂是植物脂质的一类成员，已通过醛的新型氰基酯化反应高效合成，并通过光谱分析充分表征。还合成了人造的“ V型”氰脂。
• Titanium and ruthenium binaphthyl Schiff base complexes as catalysts for asymmetric trimethylsilylcyanation of aldehydes
  作者：Xiang-Ge Zhou、Jie-Sheng Huang、Po-Hung Ko、Kung-Kai Cheung、Chi-Ming Che

  DOI：10.1039/a904330f

  日期：——

  1′-binaphthyl, toward the asymmetric trimethylsilylcyanation of some aromatic and aliphatic aldehydes demonstrated that the titanium complex of the binaphthyl Schiff base with R1 = R2 = But is one of the best catalysts for such a process, with an enantiomeric excess (e.e.) as high as 96% obtained for m-tolualdehyde. Crystal structure determination of a nitrosylruthenium complex, [RuII(L)(NO)Cl] (L is the

  Ti（OPr i）4和多种席夫碱原位形成的钛配合物的催化行为研究，主要是双萘基衍生物2,2'-双（3-R 1 -5-R 2 -2-羟基苄基亚氨基） -1,1'-联萘基对某些芳族和脂族醛的不对称三甲基甲硅烷基氰化反应表明，联萘基席夫碱的钛配合物R 1  = R 2  = Bu t是该方法的最佳催化剂，其中对于得到的对映体过量（ee），为高达96％米-tolualdehyde。亚硝酰基钌配合物[Ru II的晶体结构测定（L）（NO）Cl]（L是联萘基席夫碱的二价阴离子，R 1  ＝ R 2  ＝ Cl），表明该络合物呈顺-β构型，联萘基的二面角为70.2°。用AgPF 6处理后，钌配合物对苯甲醛的三甲基甲硅烷基氰化也显示出良好的催化性能，尽管ee较低（24％）。
• 1H and13C NMR spectra of derivatives of 2-hydroxy-3-methylbut-3-enenitrile and 2-hydroxy-3-methylbut-2-enenitrile
  作者：Jerzy W. Jaroszewski、Martin G. Ettlinger

  DOI：10.1002/mrc.1260250620

  日期：1987.6

  A series of derivatives of 2‐hydroxy‐3‐methylbut‐2‐ and ‐3‐enenitrile, including β‐D‐glucopyranosides, were obtained and their 1H and 13CNMR spectra were investigated. The spectra were assigned using lanthanide‐induced shifts, NOE difference spectroscopy and deuterium labelling.

  获得了一系列2-羟基-3-甲基丁-2-和-3-烯腈的衍生物，包括β-D-吡喃葡萄糖苷，并对其1H和13CNMR谱进行了研究。使用镧系元素引起的位移、NOE 差异光谱和氘标记分配光谱。
• Exploration of the Molecular Origin of the Azinomycin Epoxide: Timing of the Biosynthesis Revealed
  作者：Vasudha Sharma、Gilbert T. Kelly、Coran M. H. Watanabe

  DOI：10.1021/ol8018852

  日期：2008.11.6

  Streptomyces sahachiroi whole cell feeding experiments, utilizing putative precursors labeled with stable isotopes, established that the epoxide unit of the DNA cross-linked agents, azinomycin A and B, proceeds via a valine-dependent pathway and that hydroxylation and dehydration precedes formation of the terminal epoxide. Sodium 3-methyl-2-oxobutenoate, formed through a transimination reaction, was shown to be the penultimate precursor incorporated into the azinomycin epoxide.
• Synthesis of 6H-pyrrolo[1,2-c][1,2,3]triazoles and 5H-pyrrolo[1,2-d]tetrazoles: alkylation and acylation of the monoanions
  作者：Jean Pierre Dulcere、Mohamed Tawil、Maurice Santelli

  DOI：10.1021/jo00289a034

  日期：1990.1