碘丁烷-D9 | 59012-24-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 中文名称: 碘丁烷-D9
• 中文别名: 1-碘丁烷(D9)
• 英文名称: 9>-n-iodobutane
• 英文别名: <(2)H9>Butyl iodide；<2H9>butyl iodide；1-iodobutane-d₉；1-iodobutane-d9；1,1,1,2,2,3,3,4,4-nonadeuterio-4-iodo-butane；1-Iodbutan；1,1,1,2,2,3,3,4,4-nonadeuterio-4-iodobutane
• CAS: 59012-24-7
• 化学式: C₄H₉I
• 分子量: 192.948
• InChiKey: KMGBZBJJOKUPIA-YNSOAAEFSA-N

物化性质

• 熔点：
  -103 °C
• 沸点：
  130-131 °C(lit.)
• 密度：
  1.696 g/mL at 25 °C
• 闪点：
  33 °C
• 溶解度：
  易溶于可溶于氯仿、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  5
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S16,S36
• 危险类别码：
  R,R10,R20
• 危险品运输编号：
  UN 1993 3/PG 3

反应信息

• 作为反应物：
  描述：

  碘丁烷-D9 在 lithium hydroxide 、 ammonium hydroxide 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以2.00 g的产率得到tetrakis(butyl-d9)ammonium iodide
  参考文献：
  名称：

  Mechanisms of Catalyst Poisoning in Palladium-Catalyzed Cyanation of Haloarenes. Remarkably Facile C−N Bond Activation in the [(Ph₃P)₄Pd]/[Bu₄N]⁺ CN^- System

  摘要：

  Reaction paths leading to palladium catalyst deactivation during cyanation of haloarenes (eq 1) have been identified and studied. Each key step of the catalytic loop (Scheme 1) can be disrupted by excess cyanide, including ArX oxidative addition, X/CN exchange, and ArCN reductive elimination. The catalytic reaction is terminated via the facile formation of inactive [(CN)(4)Pd](2-), [(CN)(3)PdH](2-), and [(CN)(3)PdAr](2-). Moisture is particularly harmful to the catalysis because of facile CN- hydrolysis to HCN that is highly reactive toward Pd(0). Depending on conditions, the reaction of [(Ph3P)(4)Pd] with HCN in the presence of extra CN- can give rise to [(CN)(4)Pd](2-) and/or the remarkably stable new hydride [(CN)(3)PdH](2-) (NMR, X-ray). The X/CN exchange and reductive elimination steps are vulnerable to excess CN- because of facile phosphine displacement leading to stable [(CN)(3)PdAr](2-) that can undergo ArCN reductive elimination only in the absence of extra CN-. When a quaternary ammonium cation such as [Bu4N](+) is used as a phase-transfer agent for the cyanation reaction, C-N bond cleavage in the cation can occur via two different processes. In the presence of trace water, CN- hydrolysis yields HCN that reacts with Pd(0) to give [(CN)(3)PdH)(2-). This also releases highly active OH- that causes Hofmann elimination of [Bu4N](+) to give Bu3N, 1-butene, and water. This decomposition mode is therefore catalytic in H2O. Under anhydrous conditions, the formation of a new species, [(CN)(3)PdBu](2-), is observed, and experimental studies suggest that electron-rich mixed cyano phosphine Pd(0) species are responsible for this unusual reaction. A combination of experimental (kinetics, labeling) and computational studies demonstrate that in this case C-N activation occurs via an S(N)2-type displacement of amine and rule out alternative 3-center C-N oxidative addition or Hofmann elimination processes.

  DOI：

  10.1021/ja078298h
• 作为产物：
  描述：

  缬草-d9酸 在 lead(IV) acetate 、 碘 作用下， 以 四氯化碳 为溶剂， 反应 0.33h， 以47%的产率得到碘丁烷-D9
  参考文献：
  名称：

  Tsuzuki, Hirohisa; Mukumoto, Mamoru; Mataka, Shuntaro, Journal of Chemical Research, Miniprint, 1993, # 4, p. 1046 - 1058

  摘要：

  DOI：
• 作为试剂：
  描述：

  2-methyl-N-(3-phenylprop-2-yn-1-yl)-N-tosylacrylamide 在 二(三叔丁基膦)钯 、 碘丁烷-D9 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 生成 C₂₀H₁₈⁽²⁾HNO₃S
  参考文献：
  名称：

  以烷基碘化物为氢化物的钯催化1,6-烯炔的环异构化：实验和计算研究相结合

  摘要：

  已经开发了使用烷基碘作为氢化物源的钯催化的1,6-炔烃的环异构化。该方法不希望的匝数β烷基碘的-hydride消除成战略优势，有效地引起二氢-2（1 H ^） -酮和四含有具有优良的化疗和区域选择性环外双键hydropyridines。实验和计算研究支持涉及通过β-氢化物消除/氢化钯（II）迁移插入进行氢化物转移的反应机理。

  DOI：

  10.1002/adsc.201900554

文献信息

• Synthesis of the perdeuterated cellulose solvents 1-ethyl-3-methylimidazolium acetate (EMIM-OAc-d₁₄) and 1-butyl-3-methylimidazolium acetate (BMIM-OAc-d₁₈) and of 2-¹³C-butyl-3-methylimidazolium acetate
  作者：Yuko Yoneda、Gerald Ebner、Toshiyuki Takano、Fumiaki Nakatsubo、Antje Potthast、Thomas Rosenau

  DOI：10.1002/jlcr.1591

  日期：2009.5.30

  The syntheses of two perdeuterated ionic liquids (ILs), which have found use as solvents for cellulose derivatization and processing in addition, are described: 1-ethyl-3-methylimidazolium acetate (EMIM-OAc-d14) and 1-butyl–3-methylimidazolium acetate (BMIM-OAc-d18). The targets were obtained from imidazole in three-step sequences starting with butylation and ethylation, respectively. The resulting 1-alkyl imidazoles were purified, and subsequently methylated according to a novel protocol using dimethylcarbonate-d6. To obtain the 1-alkyl-3-methylimidazolium moiety, methylation of 1-alkylimidazoles proved to be superior to the conventional approach of alkylating 1-methylimidazole. Addition of acetic acid-d4 caused traceless degradation of the methylcarbonate counter anions, which were neatly exchanged for acetate. The IL 2-13C-butyl-3-methylimidazolium acetate, in which the isotopically enriched C-2 is a good NMR-indicator of side reactions and solvent–solute interactions, was synthesized according to the same reaction sequence, starting from 2-13C-1-alkylimidazole which, in turn, was obtained by reaction of glyoxale, alkylamine, ammonia and paraformaldehyde-13C. Copyright © 2009 John Wiley & Sons, Ltd.

  描述了两种全氘化离子液体（ILs）的合成，这些离子液体不仅被用作纤维素衍生化和加工的溶剂，分别是1-乙基-3-甲基咪唑鎓乙酸盐（EMIM-OAc-d14）和1-丁基-3-甲基咪唑鎓乙酸盐（BMIM-OAc-d18）。这些目标化合物分别从咪唑出发，通过三步反应合成，首先进行丁基化和乙基化。得到的1-烷基咪唑被纯化后，随后根据一种新颖的协议使用六氟化二甲基碳酸酯进行甲基化。为了获得1-烷基-3-甲基咪唑鎓基团，1-烷基咪唑的甲基化证明比传统的1-甲基咪唑烷基化方法更优。在反应中添加二氘乙酸使甲基碳酸酯阴离子无痕降解，干净地被乙酸根替代。IL 2-13C-丁基-3-甲基咪唑鎓乙酸盐，其中富含同位素的C-2是侧反应和溶剂-溶质相互作用的良好NMR指示剂，按照相同的反应序列合成，从2-13C-1-烷基咪唑开始，该化合物又是通过醛基、烷基胺、氨和甲醛-13C反应得到的。版权 © 2009 John Wiley & Sons, Ltd.
• Palladium-Catalyzed Hydrohalogenation of 1,6-Enynes: Hydrogen Halide Salts and Alkyl Halides as Convenient HX Surrogates
  作者：David A. Petrone、Ivan Franzoni、Juntao Ye、José F. Rodríguez、Amalia I. Poblador-Bahamonde、Mark Lautens

  DOI：10.1021/jacs.7b00482

  日期：2017.3.8

  corrosiveness. Experimental and computational studies support a reaction mechanism involving a crucial E-to-Z vinyl-Pd isomerization and a carbon-halogen bond-forming reductive elimination. Furthermore, rare examples of C(sp3)-Br and -Cl reductive elimination from Pd(II) as well as transfer hydroiodination using 1-iodobutane as an alternate HI surrogate are also presented.

  与在金属催化过程中处理 H2 和 CO 相关的困难导致开发了这些物种的化学替代物。尽管有许多使用这种策略的成功例子，但方便的卤化氢 (HX) 替代物在催化中的应用已经大大落后。我们现在报告使用卤化铵作为 HX 替代物来完成 Pd 催化的烯炔氢卤化。这些安全实用的盐避免了与传统 HX 源相关的许多缺点，包括毒性和腐蚀性。实验和计算研究支持涉及关键 E-to-Z 乙烯基-Pd 异构化和碳-卤素键形成还原消除的反应机制。此外，
• Synthetic Disaccharide Standards Enable Quantitative Analysis of Stored Heparan Sulfate in MPS IIIA Murine Brain Regions
  作者：Qi Qi He、Paul J. Trim、Adeline A. Lau、Barbara M. King、John J. Hopwood、Kim M. Hemsley、Marten F. Snel、Vito Ferro

  DOI：10.1021/acschemneuro.9b00328

  日期：2019.8.21

  produces fully desulfated disaccharide cleavage products which are detected by LC-MS/MS. Herein we describe the synthesis of butylated HS disaccharide standards and their use for determining the identity of major product peaks in LC-MS chromatograms from butanolysis of HS as well as the related GAGs heparin and heparosan. Furthermore, synthesis of a d9-labeled disaccharide internal standard enabled

  硫酸乙酰肝素（HS）是糖胺聚糖（GAG）家族的一种复杂多糖，会在几种称为粘多糖贮积症（MPS）的神经系统溶酶体贮积病中累积在组织中。生物样品中HS的定量对于研究MPS疾病很重要，但由于分子量高且异质性非常具有挑战性。近来，酸催化丁醇水解和随后的LC-MS / MS分析已成为测定HS的一种有前途的方法。HS的丁酰分解可产生完全脱硫的二糖裂解产物，该产物可通过LC-MS / MS检测到。本文中，我们描述了丁基化HS二糖标准品的合成及其在确定HS和相关GAG肝素和肝素的丁酸酯化LC-MS色谱图中主要产物峰的身份中的用途。此外，d9标记的二糖内标的合成使得能够开发用于HS的定量LC-MS / MS分析。该测定法用于分析MPS IIIA小鼠脑组织，揭示了受影响小鼠中各种HS二糖的丰度和区域积累方面的显着差异。
• Synthesis and analysis of isotopically stable labeled nitrosamines as mass spectrometry standards for drug impurity quality control
  作者：Volker Derdau、Martin Sandvoss

  DOI：10.1002/jlcr.4010

  日期：2023.2

  We describe a simple and easy pathway to synthesize nitrosamine mass spectrometry standards in good to moderate yields. N-alkylation of Boc-protected primary or secondary amines using stable isotope labeled alkyl halides yielded the key intermediates that were deprotected, and then, the nitrosamine was formed with sodium nitrite and sodium hydrogensulfate. Special attention to safety, disposal of waste

  我们描述了一种简单易行的合成亚硝胺质谱标准品的途径，产量高至中等。使用稳定同位素标记的烷基卤化物对 Boc 保护的伯胺或仲胺进行 N-烷基化，得到脱保护的关键中间体，然后用亚硝酸钠和硫酸氢钠形成亚硝胺。整个过程都特别注意安全、废物处理和表面清洁。
• Pheromone differences between sibling taxaDiachrysia chrysitis (linnaeus, 1758) andD. tutti (Kostrowicki, 1961) (Lepidoptera: Noctuidae)
  作者：Christer Löfstedt、Bill S. Hansson、Miklos Tòth、Gabor Szöcs、Vincas Buda、Marie Bengtsson、Nils Ryrholm、Mats Svensson、Ernst Priesner

  DOI：10.1007/bf02065993

  日期：1994.1

  The noctuid sibling taxa Diachrysia chrpsitis s. str. and D. tutti, of yet uncertain taxonomic status, have previously been shown to possess differences in morphology and to be attracted to different mixtures of the two presumed pheromone components (Z)-5-decenyl acetate and (Z)-7-decenyl acetate. Typical D. tutti males (clearly broken forewing marking) are known to respond to a 2:100 mixture of the two isomers, whereas D. chrysitis males (unbroken marking) are attracted to a 100:10 mixture. We investigated female pheromone production and male electroantennographic (EAG) response in Diachrysia families raised in the laboratory from held-collected gravid females. Extracts of individual females from typical D. tutti and D. chrysitis families were subjected to gas chromatography with simultaneous flame ionization and electroantennographic detection. All females produced mixtures of Z5- and Z7-10:OAc, but female D. chrysitis produced predominantly Z5-10:OAc