3-<1-13C>hydroxypropionitrile | 88817-63-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-<1-13C>hydroxypropionitrile
• 英文别名: ethylene cyanohydrin；3-hydroxy-(1-13C)propane-1-nitrile；3-hydroxypropionic-1-13C-nitrile；[1-(13)C]-3-hydroxypropionitrile；(1-13C)-3-hydroxypropanenitrile；[1-13C]-3-hydroxypropionitrile；3-hydroxy(113C)propanenitrile
• CAS: 88817-63-4
• 化学式: C₃H₅NO
• 分子量: 72.0678
• InChiKey: WSGYTJNNHPZFKR-VQEHIDDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  5
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  3-<1-13C>hydroxypropionitrile 在 盐酸 作用下， 生成 (1-13C)-3-chloropropionic acid
  参考文献：
  名称：

  Kinetics of cyclopropyl radical reactions. 3. Study of some 1-substituted cyclopropyl radicals by EPR spectroscopy. The inversion barrier for 1-methylcyclopropyl

  摘要：

  DOI：

  10.1021/ja00250a032
• 作为产物：
  描述：

  2-溴乙醇 生成 3-<1-13C>hydroxypropionitrile
  参考文献：
  名称：

  JENNESKENS, LEONARDUS W.;BERG, ELLEN M. M. VAN DEN;HEEMSKERK, BRAM;LUGTEN+, REC. TRAV. CHIM. PAYS-BAS., 107,(1988) N 11, C. 627-630

  摘要：

  DOI：

文献信息

• Synthesis of [3-¹³C]-, [4-¹³C]- and [11-¹³C]-porphobilinogen
  作者：Prativa B. S. Dawadi、Els A. M. Schulten、Johan Lugtenburg

  DOI：10.1002/jlcr.1602

  日期：2009.7

  [4-13C]-porphobilinogen 1a, [3-13C]-porphobilinogen 1b and [11-13C]-porphobilinogen 1c are prepared from [1-13C]-3-(tetrahydropyran-2′-yloxy)-propionaldehyde 2a, methyl [4-13C]-4-nitrobutyrate 3b and [1-13C]-isocyanoacetonitrile 5c, respectively. The building blocks 2, 3 and 5 can be prepared efficiently in any isotopomeric form. Via base-catalyzed condensation of these building blocks porphobilinogen can be enriched with 13C and 15N stable isotopes at any position and combination of positions. Copyright © 2009 John Wiley & Sons, Ltd.

  来自[1-13C]-3-(四氢吡喃-2'-基氧)-丙醛2a、甲基[4-13C]-4-硝基丁酸酯3b和[1-13C]-异氰基乙腈5c，分别合成了[4-13C]-卟胆原1a、[3-13C]-卟胆原1b和[11-13C]-卟胆原1c。构件2、3和5可以在任何同位素形式下高效制备。通过这些构件的碱催化缩合反应，可以在任何或组合的位置上丰富卟胆原的13C和15N稳定同位素。版权所有 © 2009 John Wiley & Sons, Ltd.
• Synthesis of a [13CO2H]-labelled bilirubin
  作者：Daniel F. Nogales、David A. Lightner

  DOI：10.1002/jlcr.2580340508

  日期：1994.5

  Bis-[13CO2H]-mesobilirubin-XIIIα was synthesized in 11% overall yield in 10 steps from 99% enriched K13CN. The synthetic methods are adapted to a scale of a few grams to a few milligrams.

  Bis-[13CO2H]-mesobilirubin-XIIIα的合成在10个步骤中以11%的总体收率从99%富集的K13CN合成。合成方法适用于几克到几毫克的规模。
• Biosynthesis of isoxazolin-5-one and 3-nitropropanoic acid containing glucosides in juvenile Chrysomelina
  作者：Tobias Becker、Kerstin Ploss、Wilhelm Boland

  DOI：10.1039/c6ob00899b

  日期：——

  (3-NPA) ester 2 in Chrysomelina larvae. Both structural elements originate from sequestered plant-derived β-alanine or from propanoyl-CoA that is derived from the degradation of some essential amino acids, e.g. valine. β-Alanine is converted into 3-NPA and isoxazolinone 5 by consecutive oxidations of the amino group of β-Ala. Substituting the diphospho group of α-UDP-glucose with 5 generates the isoxazolin-5-one

  稳定同位素标记的前体被用于建立金丝桃幼虫中从β-丙氨酸向异恶唑啉-5-酮葡萄糖苷1及其3-硝基丙酸酯（3-NPA）酯2的生物合成途径。这两个结构元素均源自螯合的植物衍生的β-丙氨酸或源自丙酰辅酶A，丙酰辅酶A源自某些必需氨基酸（例如缬氨酸）的降解。通过将β-丙氨酸的氨基连续氧化，将β-丙氨酸转化为3-NPA和异恶唑啉酮5。用5取代α-UDP-葡萄糖的二磷酸基团可生成异恶唑啉-5-一葡萄糖苷1，在幼虫的循环血淋巴中充当3-硝基丙酰辅酶A酯化的平台。该途径与幼虫验证辣根猿叶甲，叶甲人民呼声以及Gastrophysa蝽。
• Syntheses of (5,8-l3C2)- and (1,12-l3C2)Spermine Using Potassium (l3C)Cyanide as the 13C Source.
  作者：Keijiro SAMEJIMA、Noriko MATSUSHIMA、Masaru NIITSU、Takanobu BEPPU、Benjamin FRYDMAN

  DOI：10.1248/cpb.43.2001

  日期：——

  [5, 8-13C2]Spermine and [1, 12-13C2]spermine were prepared using [13C]KCN as the source of the label. By reaction of the latter with 1, 2-dibromoethane and ethylene chlorohydrin, the corresponding [1, 4-13C2]succinodinitrile and [CN-13C]ethylene cyanohydrin were respectively obtained. The reaction conditions were carefully adjusted so as to optimize the yields of the 13C-enriched intermediates. The nitrile residues were then reduced using sodium trifluoroacetoxyborohydride in tetrahydrofuran. [1, 4-13C2]Putrescine and [3-13C]3-aminopropanol were thus obtained. The latter was transformed into its [3-13C]3-carbobenzyloxyamidopropyl bromide derivative. The syntheses of [5, 8-13C2]spermine from the [1, 4-13C2]putrescine precursor and N-(3-bromopropyl)phthalimide, and of [1, 12-13C2]spermine from N, N'-bisbenzylputrescine and the [3-13C]3-carbobenzyloxyamidopropyl bromide precursor were then carried out using our previously reported methods, which were modified so as to maximize the yields of the 13C-enriched products.

  使用[13C]KCN作为标记源制备[5, 8-13C2]精胺和[1, 12-13C2]精胺。后者与1,2-二溴乙烷和氯丙烷反应，分别得到相应的[1,4-13C2]丁二腈和[CN-13C]乙烯氰醇。仔细调整反应条件以优化富含 13C 的中间体的产率。然后使用三氟乙酰氧基硼氢化钠的四氢呋喃溶液还原腈残余物。由此获得[1, 4-13C2]腐胺和[3-13C]3-氨基丙醇。后者被转化为其[3-13C]3-苄氧酰氨基丙基溴衍生物。由[1, 4-13C2]腐胺前体和N-(3-溴丙基)邻苯二甲酰亚胺合成[5, 8-13C2]精胺，以及由N, N'-双苄基腐胺和N-(3-溴丙基)邻苯二甲酰亚胺合成[1, 12-13C2]精胺然后使用我们之前报道的方法进行[3-13C]3-碳苄氧基酰胺基丙基溴前体的制备，该方法经过修改以最大限度地提高13C富集产物的产率。
• Synthesis of 5-[4,5-13C2]- and 5-[1,5-13C2]aminolevulinic acid
  作者：Katsumi Iida、Shinji Tokiwa、Toshihiro Ishii、Masahiro Kajiwara

  DOI：10.1002/jlcr.583

  日期：2002.6

  5-[4,5-13C2]- and 5-[1,5-13C2]Aminolevulinic acid (ALA) have been synthesized by the Gabriel condensation of potassium phthalimide with ethyl bromo[1,2-13C2]acetate (derived from [1,2-13C2]acetic acid) or ethyl bromo[2-13C]-acetate (derived from sodium [2-13C]acetate), followed by conversion to the chloride, coupling reaction with 2-ethoxycarbonylethylzinc iodide derived from ethyl 3-iodopropionate or 2-methoxy[13C]carbonylethylzinc iodide derived from methyl 3-iodo[1-13C]propionate (generated from potassium [13C]cyanide), and hydrolysis. Copyright © 2002 John Wiley & Sons, Ltd.

  5-[4,5-13C2]-和5-[1,5-13C2]氨基乙酰丙酸（ALA）是通过邻苯二甲酰亚胺钾与溴[1,2-13C2]乙酸乙酯（衍生自[ 1,2-13C2]乙酸）或溴[2-13C]-乙酸乙酯（衍生自[2-13C]乙酸钠），然后转化为氯化物，与衍生自3-乙氧基乙基碘化锌的偶联反应碘丙酸或2-甲氧基[13C]羰基乙基碘化锌衍生自3-碘[1-13C]丙酸甲酯（由[13C]氰化钾生成），并水解。版权所有 © 2002 约翰威利父子有限公司