正壬烷 | 111-84-2

• 物质功能分类: 化学试剂 - 有机试剂 - 烷烃
• 分子结构分类: 有机化合物 - 碳氢化合物 - 饱和烃
• 中文名称: 正壬烷
• 中文别名: 壬烷
• 英文名称: nonane
• 英文别名: n-Nonane
• CAS: 111-84-2
• 化学式: C₉H₂₀
• mdl: MFCD00009574
• 分子量: 128.258
• InChiKey: BKIMMITUMNQMOS-UHFFFAOYSA-N

物化性质

• 熔点：
  -53 °C
• 沸点：
  151 °C(lit.)
• 密度：
  0.72 g/mL at 20 °C
• 蒸气密度：
  4.41 (vs air)
• 闪点：
  88 °F
• 溶解度：
  In methanol, g/L: 84 at 5 °C, 95 at 10 °C, 105 at 15 °C, 116 at 20 °C, 129 at 25 °C, 142 at 30 °C, 155 at 35 °C, 170 at 40 °C (Kiser et al., 1961). Miscible with many aliphatic hydrocarbons.
• 介电常数：
  2.0（20℃）
• 暴露限值：
  NIOSH REL: TWA 200 ppm (1,050 mg/m3); ACGIH TLV: TWA 200 ppm (adopted).
• LogP：
  5.293 (est)
• 物理描述：
  N-nonane appears as a clear colorless liquid with a sharp odor. Flash point 86°F. Insoluble in water and less dense than water. Contact may irritate eyes and possibly injury the cornea. May irritate skin. Vapor inhalation may cause irritation. Prolonged inhalation may lead to breathing difficulty. Ingestion causes abdominal discomfort, nausea and diarrhea.
• 颜色/状态：
  Colorless liquid
• 气味：
  Gasoline-like odor
• 蒸汽密度：
  4.41 (NTP, 1992) (Relative to Air)
• 蒸汽压力：
  4.45 mm Hg at 25 °C /Extrapolated/
• 亨利常数：
  Henry's Law constant = 3.40 atm-cu m/mol at 25 °C (est)
• 大气OH速率常数：
  1.02e-11 cm3/molecule*sec
• 自燃温度：
  401 °F (205 °C)
• 分解：
  When heated to decomposition it emits acrid smoke and irritating fumes.
• 粘度：
  0.6696 cP at 25 °C
• 燃烧热：
  -6125 kJ/mol
• 汽化热：
  46.4 kJ/mol
• 表面张力：
  22.38 dynes/cm
• 电离电位：
  10.21 eV
• 气味阈值：
  Odor Threshold Low: 1.0 [mmHg]; Odor Threshold High: 21.0 [mmHg]; Odor threshold from AIHA
• 折光率：
  Index of refraction: 1.4058 at 20 °C
• 保留指数：
  900
• 稳定性/保质期：

  1. 稳定性：稳定。

  2. 禁配物：强氧化剂、强酸、强碱、卤素。

  3. 聚合危害：不聚合。

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  9
• 可旋转键数：
  6
• 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

ADMET

代谢

JP-8喷气燃料是由芳香烃和脂肪烃组成的复杂混合物。这项研究旨在确定半挥发性正构烷烃（壬烷C9、癸烷C10和十四烷C14）在大鼠肝脏微粒体氧化中的体外代谢速率常数。通过气相色谱测量母化合物的消失来评估代谢。将不同浓度的正构烷烃与成年雄性F-344大鼠的肝脏微粒体一起孵化。壬烷和癸烷的非线性动力学常数分别为V(max)（nmol/mg蛋白质/min）= 7.26 +/- 0.20和2.80 +/- 0.35，K(M)（uM）= 294.83 +/- 68.67和398.70 +/- 42.70。通过内在清除率（V(max)/K(M)）评估的代谢能力，壬烷大约是癸烷的四倍（0.03 +/- 0.005比0.007 +/- 0.001）...这些结果表明，正构烷烃的代谢清除率与其链长呈负相关。这些代谢速率常数将用于更新现有的非烷和癸烷的基于生理的药代动力学（PBPK）模型，作为开发JP-8的PBPK模型的一部分。

Jet propellant 8 (JP-8) jet fuel is a complex mixture of aromatic and aliphatic hydrocarbons. The aim of this study was to determine in vitro metabolic rate constants for semivolatile n-alkanes, nonane (C9), decane (C10), and tetradecane (C14), by rat liver microsomal oxidation. The metabolism was assessed by measuring the disappearance of parent compound by gas chromatography. Various concentrations of n-alkanes were incubated with liver microsomes from adult male F-344 rats. Nonlinear kinetic constants for nonane and decane were V(max) (nmol/mg protein/min) = 7.26 +/- 0.20 and 2.80 +/- 0.35, respectively, and K(M) (uM) = 294.83 +/- 68.67 and 398.70 +/- 42.70, respectively. Metabolic capacity as assessed by intrinsic clearance (V(max)/K(M)) was approximately four-fold higher for nonane (0.03 +/- 0.005) than for decane (0.007 +/- 0.001)... These results show a negative correlation between metabolic clearance and chain length of n-alkanes. These metabolic rate constants will be used to update existing physiologically based pharmacokinetic (PBPK) models for nonane and decane as part of developing a PBPK model for JP-8.

来源:Hazardous Substances Data Bank (HSDB)

代谢

壬烷，是喷气推进燃料8（JP-8）的一个组成部分，在混合人肝微粒体（pHLM）的作用下代谢为2-壬醇和2-壬酮。细胞色素P450（CYP）同种物1A2、2B6和2E1将壬烷代谢为2-壬醇，而酒精脱氢酶、CYPs 2B6和2E1将2-壬醇代谢为2-壬酮。壬烷和2-壬醇对睾酮、雌二醇或N,N-二乙基-m-甲苯酰胺（DEET）的代谢没有显著影响，但抑制了甲萘威的代谢。JP-8对睾酮、雌二醇和甲萘威的代谢有适度的抑制作用，但对DEET的代谢影响更为显著。JP-8被显示能抑制CYPs 1A2和2B6介导的DEET代谢，这表明至少JP-8的一些成分可能被CYPs 1A2和/或2B6代谢。

Nonane, a component of jet-propulsion fuel 8 (JP-8), is metabolized to 2-nonanol and 2-nonanone by pooled human liver microsomes (pHLM). Cytochrome P450 (CYP) isoforms 1A2, 2B6 and 2E1 metabolize nonane to 2-nonanol, whereas alcohol dehydrogenase, CYPs 2B6 and 2E1 metabolize 2-nonanol to 2-nonanone. Nonane and 2-nonanol showed no significant effect on the metabolism of testosterone, estradiol or N,N-diethyl-m-toluamide (DEET), but did inhibit carbaryl metabolism. JP-8 showed modest inhibition of testosterone, estradiol and carbaryl metabolism, but had a more significant effect on the metabolism of DEET. JP-8 was shown to inhibit CYPs 1A2 and 2B6 mediated metabolism of DEET, suggesting that at least some of the components of JP-8 might be metabolized by CYPs 1A2and/or 2B6.

来源:Hazardous Substances Data Bank (HSDB)

代谢

九烷在大鼠体内以相对较高的速率被代谢成羟基衍生物，然后转化为相应的酮形式，这是通过含有混合功能氧化酶系统的细胞色素P450来确定的。

Nonane is metabolized in the rat at relatively high rates to hydroxyl derivatives prior to conversion into the corresponding keto form, as determined with a cytochrome P450 containing mixed function oxidase system.

来源:Hazardous Substances Data Bank (HSDB)

代谢

先前的研究已经证实，氯吡硫磷（CPS）、氟虫腈和非烷都可以被人肝微粒体（HLM）和多种细胞色素P450（CYP）同种物代谢。然而，这三种底物之间的代谢相互作用尚未被描述。在本研究中，探讨了CPS与HLM或CYP同种物共同培养或预培养对氟虫腈或非烷作为底物的影响。在共同培养和预培养实验中，CPS显著抑制了HLM对氟虫腈或非烷的代谢，尽管CPS对氟虫腈代谢的抑制效果比对非烷更有效。CPS显著抑制了CYP3A4对氟虫腈以及CYP2B6对非烷的代谢。在两种情况下，与CPS预培养相比，共同培养导致的抑制更大，这表明这种抑制是基于机制的。

Previous studies have established that chlorpyrifos (CPS), fipronil, and nonane can all be metabolized by human liver microsomes (HLM) and a number of cytochrome P450 (CYP) isoforms. However, metabolic interactions between these three substrates have not been described. In this study the effect of either coincubation or preincubation of CPS with HLM or CYP isoforms with either fipronil or nonane as substrate was investigated. In both co- and preincubation experiments, CPS significantly inhibited the metabolism of fipronil or nonane by HLM although CPS inhibited the metabolism of fipronil more effectively than that of nonane. CPS significantly inhibited the metabolism of fipronil by CYP3A4 as well as the metabolism of nonane by CYP2B6. In both cases, preincubation with CPS caused greater inhibition than coincubation, suggesting that the inhibition is mechanism based.

来源:Hazardous Substances Data Bank (HSDB)

代谢

Fischer 344雄性大鼠通过灌胃给予正壬烷后，尿液中含有的代谢物包括γ-戊内酯、δ-己内酯、2,5-己二酮、δ-庚内酯、1-庚醇、2-壬醇、3-壬醇、4-壬醇、4-壬酮和5-甲基-2-(3-氧代丁基)呋喃。代谢过程强烈倾向于形成单醇和内酯，这些是适当取代的羟基羧酸的产品。使用气相色谱（GC）和气相色谱/质谱（GC/MS）识别了代谢物。高压液相色谱（HPLC）使得能够在给予正壬烷的大鼠尿液中检测到丁二酸和戊二酸这两种二羧酸。

The urinary metabolites of n-nonane in male Fischer 344 rats, after administering the hydrocarbon by gavage, included gamma-valerolactone, delta-hexanolactone, 2,5-hexanedione, delta-heptanolactone, 1-heptanol, 2-nonanol, 3-nonanol, 4-nonanol, 4-nonanone and 5-methyl-2-(3-oxobutyl)furan. Metabolism strongly favored the formation of monoalcohols and lactones, which are the products of appropriately substituted hydroxy carboxylic acids. The metabolites were identified using gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). High pressure liquid chromatography (HPLC) permitted the detection of the dicarboxylic acids malonic acid and glutaric acid in the n-nonane dosed rat urines.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 暴露途径

该物质可以通过吸入其蒸汽和摄入进入人体。

The substance can be absorbed into the body by inhalation of its vapour and by ingestion.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 暴露途径

吸入，吞食，皮肤和/或眼睛接触

inhalation, ingestion, skin and/or eye contact

来源:The National Institute for Occupational Safety and Health (NIOSH)

毒理性

• 症状

眼睛、皮肤、鼻子、喉咙刺激；头痛、嗜睡、眩晕、混乱、恶心、震颤、不协调；化学性肺炎（吸入液体）

irritation eyes, skin, nose, throat; headache, drowsiness, dizziness, confusion, nausea, tremor, incoordination; chemical pneumonitis (aspiration liquid)

来源:The National Institute for Occupational Safety and Health (NIOSH)

毒理性

• 吸入症状

咳嗽。喉咙痛。嗜睡。眩晕。共济失调。抽搐。昏迷。

Cough. Sore throat. Drowsiness. Dizziness. Ataxia Convulsions. Unconsciousness.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 皮肤症状

干燥的皮肤。红斑。

Dry skin. Redness.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

吸收、分配和排泄

尽管这种暴露场景是职业常态，但经皮涂抹的喷气燃料碳氢化合物（HC）通过预先暴露于JP-8的皮肤的吸收尚未被研究。将猪暴露于浸泡了JP-8的棉布1天和4天，并每天重复暴露。预处理和未处理的皮肤随后被切割并放置在体外扩散细胞中。五个暴露皮肤的细胞和四个未暴露皮肤的细胞被用含有非烷、癸烷、十一烷、十二烷、十三烷、十四烷、十五烷、十六烷、乙基苯、邻二甲苯、三甲基苯（TMB）、环己基苯（CHB）、萘和二甲基萘（DMN）的14种不同HC的水+乙醇（50:50）作为稀释剂的混合物处理。另外五个含有JP-8暴露皮肤的细胞只被稀释剂处理，以确定喷气燃料HC在皮肤中的残留潜力。数据显示，通过1天和4天JP-8预暴露皮肤的吸收，非烷、十一烷、十二烷和十三烷的吸收分别增加了2-3倍和3-4倍...计算了研究HC的通量、扩散率和渗透性参数。燃料预暴露皮肤中HC吸收增加的可能机制可能是通过电子显微镜指示的角质层脂质提取。这项研究表明，喷气燃料HC的单次剂量应用数据不能用于预测重复暴露的毒性潜力，并且对于某些化合物，可能在暴露后几天内持续吸收。

The percutaneous absorption of topically applied jet fuel hydrocarbons (HC) through skin previously exposed to JP-8 has not been investigated, although this exposure scenario is the occupational norm. Pigs were exposed to JP-8 soaked cotton fabrics for 1 and 4 days with repeated daily exposures. Pre-treated and untreated skin was then dermatomed and placed in in-vitro diffusion cells. Five cells with exposed skin and four cells with unexposed skin were dosed with a mixture of 14 different HC consisting of nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, ethyl benzene, o-xylene, trimethyl benzene (TMB), cyclohexyl benzene (CHB), naphthalene, and dimethyl naphthalene (DMN) in water + ethanol (50:50) as diluent. Another five cells containing JP-8 exposed skin were dosed with diluent only in order to determine the residue potential of jet fuel HC in skin. The data indicated that there was 2-3-fold and 3-4-fold increase in absorption of nonane, undecane, dodecane and tridecane through 1 and 4 days JP-8 pre-exposed skin respectively... The absorption parameters of flux, diffusivity and permeability were calculated for the studied HC. The possible mechanism of increased HC absorption in fuel pre-exposed skin may be via lipid extraction from stratum corneum as indicated by electron microscopy. This study suggests that single dose application data for jet fuel HC cannot be used to predict the toxic potential for repeated exposures and that for certain compounds, persistent absorption may occur days post-exposure.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

呼吸道吸收...是非烷进入系统循环的主要途径。...非烷的皮肤生物利用度预计非常低。...脂肪组织、肝脏和大脑似乎对长链烷烃如非烷有最大的亲和力...。

Respiratory absorption ... represents the major route by which nonane enters systemic circulation. ... The dermal bioavailability of nonane is expected to be very low. ... Adipose tissue, liver, and brain appear to have the greatest affinity for long chain alkanes such as nonane ... .

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 职业暴露等级：
  A
• 职业暴露限值：
  TWA: 200 ppm (1050 mg/m3)
• TSCA：
  Yes
• 危险等级：
  3
• 危险品标志：
  N
• 安全说明：
  S23,S24/25,S62
• 危险类别码：
  R51/53,R10
• WGK Germany：
  3
• 海关编码：
  2901100000
• 危险品运输编号：
  UN 1920 3/PG 3
• RTECS号：
  RA6115000
• 包装等级：
  III
• 危险类别：
  3
• 危险标志：
  GHS02,GHS07,GHS08,GHS09
• 危险性描述：
  H226,H304,H315,H336,H410
• 危险性防范说明：
  P210,P273,P301 + P310,P304 + P340 + P312,P331,P391
• 储存条件：
  储存注意事项：应将物品存放在阴凉、通风良好的库房中，并远离火源和热源，库温不宜超过37℃，确保容器密封良好。需与氧化剂分开存放，严禁混储。使用防爆型照明和通风设施，并禁止使用可能产生火花的机械设备和工具。储存区应配备泄漏应急处理设备及合适的收容材料。

SDS

第一部分：化学品名称

制备方法与用途

用途：用作色谱分析标准物质和溶剂，也用于有机合成。

类别：易燃液体

毒性分级：低毒

急性毒性：

• 吸入 - 大鼠 LC50: 3200 PPM/4小时
• 静脉注射 - 小鼠 LD50：218 毫克/公斤

刺激数据：

• 皮肤接触 - 猪 180 毫克/24小时，轻度刺激

爆炸物危险特性： 与空气混合可爆。

可燃性危险特性： 遇明火、高温或氧化剂易燃；燃烧时会产生刺激烟雾。

储运特性： 应存放在通风、低温和干燥的库房中，并且要与氧化剂分开存放。

灭火剂： 干粉、二氧化碳、泡沫或1211灭火剂。

职业标准：

• 时间加权平均容许浓度（TWA）：1050 毫克/立方米
• 短时间暴露限值（STEL）：1300 毫克/立方米

反应信息

• 作为反应物：
  描述：

  正壬烷 在 sodium hydroxide 、 氯 、 二氧化氮 作用下， 170.0~380.0 ℃ 、1.96 MPa 条件下， 生成 1-壬醇
  参考文献：
  名称：

  Nekrasowa, Zhurnal Obshchei Khimii, 1958, vol. 28, p. 1561;engl.Ausg.S.1610

  摘要：

  DOI：
• 作为产物：
  描述：

  1-壬醇 在 五氧化二钒 、 铁粉 氢气 作用下， 生成 正壬烷
  参考文献：
  名称：

  铁催化剂上醇和酮的有效气相脱氧

  摘要：

  讨论了一种在600 K和1-2·10 5 Pa下铁催化剂上将醇和酮气相脱氧为烃的方法。

  DOI：

  10.1016/s0040-4039(00)98301-1
• 作为试剂：
  描述：

  在 lithium aluminium tetrahydride 、 正壬烷 、 硫酸 、 氧气 、 manganese(II) stearate 作用下， 反应 11.0h， 生成 4-庚醇
  参考文献：
  名称：

  Intramolecular H-transfer reactions during the Decomposition of Alkylhydroperoxides in hydrocarbons as the solvents

  摘要：

  DOI：

  10.1002/prac.19943360109

文献信息

• Hydrodefluorination and Other Hydrodehalogenation of Aliphatic Carbon−Halogen Bonds Using Silylium Catalysis
  作者：Christos Douvris、C. M. Nagaraja、Chun-Hsing Chen、Bruce M. Foxman、Oleg V. Ozerov

  DOI：10.1021/ja100605m

  日期：2010.4.7

  Trialkylsilylium cation equivalents partnered with halogenated carborane anions (such as Et(3)Si[HCB(11)H(5)Cl(6)]) function as efficient and long-lived catalysts for hydrodehalogenation of C-F, C-Cl, and C-Br bonds with trialkylsilanes as stoichiometric reagents. Only C(sp(3))-halogen bonds undergo this reaction. The range of C-F bond-containing substrates that participate in this reaction is quite broad and

  与卤化碳硼烷阴离子（如 Et(3)Si[HCB(11)H(5)Cl(6)]）配合使用的三烷基甲硅烷阳离子等价物可作为 CF、C-Cl 和 C 加氢脱卤的高效长寿命催化剂-Br 与作为化学计量试剂的三烷基硅烷键合。只有 C(sp(3))-卤素键会发生此反应。参与该反应的含 CF 键的底物范围非常广泛，包括简单的烷基氟化物、苯并三氟化物和具有连接到脂肪链的全氟烷基的化合物。然而，CF(4) 已证明对这种反应免疫。用一系列烷基氯和三氯化苯进行加氢脱氯，仅用伯烷基溴底物研究加氢脱溴。竞争性实验确定了催化系统在活化伯烷基卤化物中较轻卤化物的碳-卤键方面具有明显的动力学偏好。相反，在一锅实验中，C(6)F(5)CCl(3) 的加氢脱氯比 C(6)F(5)CF(3) 的加氢脱氟进行得快得多。Et(3)Si[HCB(11)H(5)Cl(6)] 的固态结构由 X 射线衍射方法确定。
• The iridium-catalyzed decarbonylation of aldehydes under mild conditions
  作者：Tomohiro Iwai、Tetsuaki Fujihara、Yasushi Tsuji

  DOI：10.1039/b813171f

  日期：——

  The catalytic decarbonylation of aldehydes has been developed using commercially available [IrCl(cod)](2) and PPh(3) under mild conditions, and the method could be widely applicable to various substrates with different functionalities.

  醛的催化脱羰已开发出使用市售的[IrCl（cod）]（2）和PPh（3）在温和的条件下，该方法可广泛适用于具有不同功能的各种基材。
• Reactivities of mixed organozinc and mixed organocopper reagents: 9. Solvent dependence of group transfer selectivity in sp3C coupling and acylation of mixed diorganocuprates and diorganozincs
  作者：Ender Erdik、Fatma Eroğlu、Melike Kalkan、Özgen Ömür Pekel、Duygu Özkan、Ebru Z. Serdar

  DOI：10.1016/j.jorganchem.2013.07.037

  日期：2013.11

  diorganocuprates in their alkyl coupling in THF depends on N- or O-donor solvents as cosolvents. Selective n-Bu group transfer is observed in room temperature alkylation of Grignard reagent derived stoichiometric n-BuPhCuMgBr reagent in THF:cosolvent and solvation effects do not change the group transfer ability. However, in the alkylation of catalytic mixed cuprates derived from CuI catalyzed n-BuPh2ZnMgBr

  混合的二有机癸酸酯在烷基在THF中的偶联中，有机基转移的选择性和/或反应性取决于N-或O-供体溶剂作为助溶剂。在THF：助溶剂中，在Grignard试剂衍生的化学计量n- BuPhCuMgBr试剂的室温烷基化中观察到选择性n- Bu基团转移，并且溶剂化作用不会改变基团转移能力。然而，在催化混合铜酸盐的烷基化从催化的CuI衍生Ñ -BuPh 2 ZnMgBr和Ñ -Bu 2 PhZnMgBr，基团转移能力取决于溶剂化作用，它可以通过使用N-或O-供体的溶剂进行控制。在CuI催化的烷基化混合锌酸盐n- BuPh的烷基化中2 ZnMgBr并且还Ñ -Bu 2 PhZnMgBr在THF中在回流温度下Ph基团转移发生（Ñ -Bu /植转印比为1：9和4：分别为6，），而Ñ在THF -Bu转印增加：NMP（1 ：1）的n -Bu / Ph转移比分别为4：6和8：2。n -BuPhZn的烯丙基化中的基团
• Borohydride-Mediated Radical Addition Reactions of Organic Iodides to Electron-Deficient Alkenes
  作者：Takuji Kawamoto、Shohei Uehara、Hidefumi Hirao、Takahide Fukuyama、Hiroshi Matsubara、Ilhyong Ryu

  DOI：10.1021/jo500464q

  日期：2014.5.2

  Cyanoborohydrides are efficient reagents in the reductive addition reactions of alkyl iodides and electron-deficient olefins. In contrast to using tin reagents, the reaction took place chemoselectively at the carbon–iodine bond but not at the carbon–bromine or carbon–chlorine bond. The reaction system was successfully applied to three-component reactions, including radical carbonylation. The rate constant

  氰基硼氢化物是烷基碘化物和缺电子烯烃的还原加成反应中的有效试剂。与使用锡试剂相反，该反应在碳碘键上发生化学选择，而在碳溴或碳氯键上没有发生。该反应体系已成功应用于三组分反应，包括自由基羰基化。通过动力学竞争法，在25°C下从氰基硼氢化四丁基铵中伯烷基脱氢的速率常数估计为<1×10 4 M –1 s –1。该值比氢化三丁基锡的值小3个数量级。
• Reevaluation of the Palladium/Carbon-Catalyzed Decarbonylation of Aliphatic Aldehydes
  作者：Igor Opsenica、Vladimir Ajdačić、Andrea Nikolić、Michael Kerner、Peter Wipf

  DOI：10.1055/s-0037-1610433

  日期：2018.8

  An improved method for the decarbonylation of aliphatic ­aldehydes by using a commercially available Pd/C catalyst is described. The reaction conditions are suitable for linear, cyclic, or sterically demanding substrates, as they afford the corresponding alkanes in yields of up to 99%. In addition, this Pd/C-catalyzed method exhibits good functional-group tolerance. A comparison of previously reported

  描述了一种使用市售 Pd/C 催化剂对脂肪醛进行脱羰的改进方法。反应条件适用于线性、环状或空间要求高的底物，因为它们以高达 99% 的产率提供相应的烷烃。此外，这种 Pd/C 催化的方法表现出良好的官能团耐受性。先前报道的方法与当前方法的比较表明，反应条件对反应结果起着至关重要的作用。该方法还可用于合成工业上重要化合物的两步反应序列。

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