乙二醇甲醚乙酸酯 | 110-49-6

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 乙二醇甲醚乙酸酯
• 中文别名: 甲二醇乙醚乙酸酯；乙酸-2-甲氧乙酯；乙酸乙二醇甲醚；乙二醇独甲醚乙酸酯；乙酸乙二醇单甲醚酯；乙二醇一甲醚乙酸酯；2-甲氧基乙基乙酸酯；乙酸-2-甲氧基乙酯；2-甲氧基乙酸乙酯；乙酸甲基溶纤剂；2-甲烷氧基乙基乙酯；乙二醇甲醚醋酸酯
• 英文名称: 2-methoxyethyl acetate
• 英文别名: 2-methoxyethanol acetate
• CAS: 110-49-6
• 化学式: C₅H₁₀O₃
• mdl: MFCD00008719
• 分子量: 118.133
• InChiKey: XLLIQLLCWZCATF-UHFFFAOYSA-N

物化性质

• 熔点：
  −65 °C(lit.)
• 沸点：
  145 °C(lit.)
• 密度：
  1.009 g/mL at 25 °C(lit.)
• 闪点：
  111 °F
• 溶解度：
  溶于乙醇和乙醚(Weast,1986)。
• 最大波长(λmax)：
  λ: 254 nm Amax: 1.00λ: 275 nm Amax: 0.15λ: 300 nm Amax: 0.05λ: 350-400 nm Amax: 0.01
• 暴露限值：
  NIOSH REL: TWA 0.1 ppm (0.5 mg/m3), IDLH 200 ppm; OSHA PEL: TWA 25 ppm (120 mg/m3); ACGIH TLV: TWA 5 ppm (24 mg/m3).
• 物理描述：
  Ethylene glycol monomethyl ether acetate appears as a clear colorless liquid with a pleasant odor. Flash point of 135°F. Denser than water and soluble in water. Vapors are heavier than air.
• 颜色/状态：
  Colorless liquid
• 气味：
  Pleasant odor
• 蒸汽密度：
  4.07 (NTP, 1992) (Relative to Air)
• 蒸汽压力：
  7.0 mm Hg at 20 °C
• 自燃温度：
  394 °C, 740 °F
• 分解：
  When heated to decomposition it emits acrid smoke and fumes.
• 粘度：
  1.1 cP at 25 °C
• 汽化热：
  At 25 °C = 50.27 kcal/mole; at boiling point = 43.9 kcal/mole
• 表面张力：
  Neat product = 32.1 dynes/cm at 25 °C; 25% aqueous = 54.3 dynes/cm at 25 °C
• 折光率：
  Index of refraction: 1.4019 at 20 °C/D
• 相对蒸发率：
  0.3 (n-Butyl acetate = 1)
• 保留指数：
  756;757;773
• 稳定性/保质期：
  1. **稳定性**：稳定。 2. **禁配物**：酸类、碱类、强氧化剂。 3. **聚合危害**：不聚合。

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

ADMET

代谢

...必须被身体水解，因为它会产生类似于乙二醇甲醚引起的毒性症状。也可能形成一些乙醛。

...Must be .../hydrolyzed/ by body because it gives rise to toxic signs similar to those caused by ethylene glycol methyl ether. Some acetaldehyde may also be formed.

来源:Hazardous Substances Data Bank (HSDB)

代谢

这个酯在体内水解成2-甲氧基乙醇。

The ester hydrolyzes in body to 2-methoxyethanol.

来源:Hazardous Substances Data Bank (HSDB)

代谢

EGMEA在小鼠鼻部组织中很容易被代谢成EGME。EGME进一步被酒精脱氢酶代谢为2-甲氧基乙酸，这是一种已知的生殖和发育毒性物质。

EGMEA is readily metabolized in mouse nasal tissues to produce EGME. EGME is further metabolized by alcohol dehydrogenase to 2-methoxyacetic acid, a known reproductive and developmental toxicant.

来源:Hazardous Substances Data Bank (HSDB)

代谢

小鼠体外鼻腔黏膜羧酸酯酶活性与其他小鼠组织活性进行了比较，并与大鼠、家兔或犬在接触2-MEA或2-EEA时的鼻腔黏膜羧酸酯酶活性进行了比较。发现小鼠鼻腔羧酸酯酶的比活性与肝脏相似，但高于肾脏、肺或血液中的活性。小鼠的鼻腔黏膜羧酸酯酶活性与犬相似，略高于大鼠，几乎比家兔高六倍。这些体外研究表明，在完整动物体内可能会发生相当大的水解作用，导致在初始进入途径处形成醋酸。

The in vitro nasal mucosal carboxylesterase activity of mice was compared to the activity of other mice tissues and to the nasal mucosal carboxylesterase activity of rats, rabbits, or dogs when exposed to 2-MEA or 2-EEA. The specific activity in nasal carboxylase was found to be similar to that of the liver in mice, but it was greater than the activity found in the kidney, lung, or blood of mice. Nasal mucosal carboxyl-esterase activity of mice was comparable to that of dogs, slightly higher than the activity in rats, and nearly six-fold higher than the activity in rabbits. These in vitro studies suggest that considerable hydrolysis may occur in the intact animal, resulting in the formation of acetic acid at the initial route of entry.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

乙二醇的甲基和乙基醚，即2-甲氧基乙醇（2-ME）酯、2-甲氧基乙醋酸（2-MEA）和2-乙氧基乙醋酸（2-EEA）都是稳定的，并且都与水相溶（或者对于2-EEA来说，在水中非常溶解），并且与大量的有机溶剂相溶。这些乙二醇醚在水中的溶解性和它们相对较低的蒸气压可能会导致在没有降解的情况下在水体中积累。然而，土壤、污泥和水体中的微生物降解似乎防止了这种可能性。由于使用乙二醇醚作为挥发性溶剂而造成的大气排放导致最大的环境暴露。对环境中生物体的影响：2-ME和2-EE对微生物和水生动物的毒性似乎很低。乙二醇醚醋酸（2-MEA和2-EEA）对鱼类的毒性要大得多。2-EEA对黑头鱼的头部的LC50是46 mg/L，而2-MEA对银鱼和蓝鳃鱼的LC50是45 mg/L。对实验动物和体外测试系统的影响：系统毒性：2-ME和2-EE对实验动物的毒性研究比2-MEA和2-EEA要广泛得多。2-ME和2-EE及其醋酸酯在单次暴露后具有相似的致死性，并且无论是通过皮肤、口服还是吸入途径，它们都显示出低急性致死性。口服LD60值对于多种物种的范围在900到3400 mg/kg体重之间，对于2-ME，1400到5500 mg/kg对于2-EE，1250到3930 mg/kg对于2-MEA，以及1300到5100 mg/kg对于2-EEA。对实验动物进行短期吸入暴露（长达90天）的高浓度（> 9313 mg 2-ME/cu m）...已经显示出对血液参数、神经系统、睾丸、胸腺、肾脏、肝脏和肺的不利影响。在较低的暴露水平下，观察到对造血系统和睾丸的影响。例如，在大约93到930 mg/cu m的水平下通过吸入暴露于2-ME的大鼠13周，仅在高剂量下出现红细胞压积和白细胞、血红蛋白、血小板和血清蛋白浓度的降低，而同样暴露的兔子在930 mg/cu m时除了降低血液参数外，胸腺大小也减小。2-ME的致突变性已经在使用细菌和哺乳动物细胞的体外系统中进行了研究。尽管大多数研究得到了阴性结果，但在研究染色体畸变（在6830 ug/mL或更高）和姐妹染色单体交换（3170 ug/mL或更高）时，有报道称在CHO细胞中2-ME浓度非常高时得到了阳性致突变性结果。然而，体内研究对于染色体畸变和微核是阴性的。2-ME对雄性生殖系统的影响已经在通过口服和吸入暴露于啮齿动物的实验中进行了深入研究。在生精管的生精上皮中一致地观察到了退行性变化。在大鼠口服2-ME 1-11天之后，在100 mg/kg体重或更高的剂量水平下，观察到精子数量减少和精子运动能力和形态的改变。在尸检时，在睾丸中看到了明显的组织学损伤。未观察到效果水平（NOEL）是50 mg/kg。在暴露于200 mg/kg后8周，仍然可以看到生育能力降低。在单次口服剂量为250 mg 2-ME/kg或更高后进行的生育研究发现，在大鼠和小鼠给药后5周完全不育，在125 mg/kg时可以看到一些生育能力下降。当研究吸入途径时，在2-ME暴露后也看到了类似的睾丸退行性变化。在单次暴露（4小时）1944 mg/m3或更高时观察到效果，但在933 mg/cu m时没有。在大鼠13周暴露（每天6小时，每周5天）后NOEL值为311 mg/cu m，而在小鼠9次暴露（每次6小时）11天后为933 mg/cu m。在兔子13周（每天6小时，每周5天）暴露于2-ME后，在311 mg/cu m或更高时对睾丸的影响非常明显；在93 mg/cu m时看到了边缘效果，并且没有确定NOEL。在通过所有管理途径（即口服、吸入和皮肤）暴露后，在几种实验室动物物种中观察到了发育毒性。2-ME在小鼠、大鼠、兔子和猴子中产生了致畸效应。尽管还没有对2-MEA进行发育毒性的测试，但代谢轮廓表明可以合理地预期2-MEA的毒性类似于2-ME。对于2-ME，具有最广泛的剂量/反应数据（剂量为31.25到1000 mg/kg每天）。在这个使用小鼠的灌胃研究中（在妊娠的第7到14天给予2-ME），母体毒

... The methyl and ethyl ethers of ethylene glycol, ie 2- methoxyethanol (2-ME) esters, 2-methoxyethyl acetate (2-MEA) and 2-ethoxyethyl acetate (2- EEA) ... are all stable, and are all miscible with (or in the case of 2-EEA very soluble in) water and miscible with a large number of organic solvents. ... The solubility of these glycol ethers in water and their relatively low vapor pressure could result in their build-up in water in the absence of degradation. However, degradation by microorganisms in soil, sewage sludge, and water appears to prevent this possibility. Atmospheric emissions resulting from the use of glycol ethers as evaporative solvents result in the greatest environmental exposure.... Effects on Organisms in the Environment: The toxicity of 2-ME and 2-EE to microorganisms and aquatic animals appears to be low. ... The glycol ether acetates (2-MEA and 2-EEA) are far more toxic to fish. The LC50 of 2-EEA for fathead minnows is 46 mg/L and that of 2-MEA for tidewater silverfish and bluegills is 45 mg/L. ... Effects on Experimental Animals and In Vitro Test Systems: Systemic toxicity: The toxicity of 2-ME and 2-EE to experimental animals has been much more widely studied than that of 2-MEA and 2-EEA. 2-ME and 2-EE and their acetates have similar lethalities after single exposures and they show low acute lethality whether exposure is via the dermal, oral, or inhalation route. Oral LD60 values for a variety of species range between 900 and 3400 mg/kg body weight for 2-ME, 1400 and 5500 mg/kg for 2-EE, 1250 and 3930 mg/kg for 2-MEA, and 1300 and 5100 mg/kg for 2-EEA. ... Short-term inhalation exposure (up to 90 days) of experimental animals to high concentrations (> 9313 mg 2-ME/cu m ... has been shown to lead to adverse effects on blood parameters, the nervous system, and testes, thymus, kidney, liver, and lung. At lower exposure levels, effects are observed on the hemopoietic system and testes. For example, rats exposed by inhalation to 2-ME for 13 weeks at levels between 93 and 930 mg/cu m exhibited reduced packed cell volume and white blood cell, hemoglobin, platelet, and serum protein concentrations at the highest dose only, while similarly exposed rabbits had decreased thymus size, in addition to the decreased blood parameters, at 930 mg/cu m. ... The mutagenicity of 2-ME has been investigated in a range of in vitro systems using bacteria and mammalian cells. Although most studies yielded negative results, there were reports of positive mutagenicity results at very high 2-ME concentrations in CHO cells when investigated for chromosome aberration (at 6830 ug/mL or more) and sister chromatid exchange (3170 ug/mL or more). However, in vivo studies for chromosome aberrations and micronuclei were negative. ... The effect of 2-ME on the male reproductive system has been intensively investigated following both oral and inhalation exposure in rodents. Degenerative changes in the germinal epithelium of the seminiferous tubules were consistently noted. ... Oral dosing of rats with 2-ME for 1-11 days resulted in a dose-related decrease in sperm count and changes in sperm motility and morphology at dose levels of 100 mg/kg body weight or more. Marked histological damage was seen in the testes at autopsy. The no-observed-effect level (NOEL) was 50 mg/kg. Reduced fertility was still evident 8 weeks after exposure to 200 mg/kg. ... Fertility studies following a single oral dose of 250 mg 2-ME/kg or more revealed complete sterility in both rats and mice at 5 weeks post dosing, some decrease in fertility being seen at 125 mg/kg. When the inhalation route was investigated, similar degenerative changes in the testes were seen with 2-ME. Effects were observed following a single exposure (4 hr) to 1944 mg/m3 or more but not to 933 mg/cu m. NOEL values were 311 mg/cu m in rats following exposure for 13 weeks (6 hr/day, 5 day/week) and 933 mg/cu m (6 hr/day) in mice following exposure on 9 occasions over 11 days. Exposure of rabbits to 2-ME for 13 weeks (6 hr/day, 5 days/week) resulted in marked effects on the testes at 311 mg/cu m or more; marginal effects were seen at 93 mg/cu m, and a NOEL was not identified. ... Developmental toxicity has been observed in several species of laboratory animals following exposure by all routes of administration, i.e. oral, inhalation, and dermal. 2-ME produced teratogenic effects in mice, rats, rabbits, and monkeys. ... Although 2-MEA has not been tested for developmental toxicity, metabolic profiles suggest that it is reasonable to expect that 2-MEA would have a toxicity similar to that of 2-ME. The widest range of dose/response data (doses of 31.25 to 1000 mg/kg per day) is available for 2-ME. In this gavage study using mice, (2-ME was administered on days 7 to 14 of gestation), the NOEL for maternal toxicity was 125 mg/kg per day. However, malformations were observed at 62.5 mg/kg per day and skeletal variations at 31.25 mg/kg per day. A NOEL for developmental toxicity was not reported. In single-dose studies, mice were treated with 2-ME by gavage on gestation day 11; 100 mg/kg was not fetotoxic, while 175 mg/kg produced digit defects without other signs of maternal or fetal toxicity. Cardiovascular defects and ECG abnormalities were observed in neonatal rats following treatment on days 7 to 13 of gestation with 25 mg/kg per day. Since that was the lowest dose tested, this study yielded no developmental NOEL (maternal toxicity was not observed at that dose). Similarly, no NOEL for developmental toxicity could be determined when monkeys were treated by gavage with 2-ME at 0.16, 0.32, or 0.47 mmol/kg per day on days 20 to 45 of gestation. Fetotoxicity in mice and rats and malformations in rabbits were observed following exposure by inhalation to 2-ME at 156 mg/m3. For all three species, the NOEL for developmental effects was 31 mg/cu m. However, behavioral and neurochemical alterations were seen in the offspring of rats exposed to 78 mg 2-ME/cu m on days 7-13 or 14-20 of gestation. Following inhalation exposure of rats (743 mg/m3) and rabbits (589 mg/m3), 2-EE was found to be teratogenic (in the presence of slight maternal toxicity). ... Information on the toxic effects of these four glycol ethers on humans is limited. The results from the few case reports and workplace epidemiological studies are consistent with the adverse effects seen in experimental animals. ...

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、通过皮肤接触以及摄入进入人体。

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

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

毒理性

• 暴露途径

吸入，皮肤吸收，吞食，皮肤和/或眼睛接触

inhalation, skin absorption, ingestion, skin and/or eye contact

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

毒理性

• 症状

眼睛、鼻子、喉咙刺激；肾脏、大脑损伤；在动物中：麻醉；生殖、致畸作用

irritation eyes, nose, throat; kidney, brain damage; In Animals: narcosis; reproductive, teratogenic effects

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

毒理性

• 吸入症状

晕眩。嗜睡。头痛。

Dizziness. Drowsiness. Headache.

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

吸收、分配和排泄

可以通过皮肤、肺或消化道吸收。

... Can be absorbed via the skin, lungs or GI tract.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 职业暴露等级：
  C
• 职业暴露限值：
  TWA: 0.1 ppm (0.5 mg/m3) [skin]
• 危险等级：
  3
• 立即威胁生命和健康浓度：
  200 ppm
• 危险品标志：
  T
• 安全说明：
  S45,S53
• 危险类别码：
  R60,R20/21/22,R61
• WGK Germany：
  1
• 海关编码：
  2915390090
• RTECS号：
  KL5950000
• 包装等级：
  III
• 危险类别：
  3
• 危险标志：
  GHS02,GHS07,GHS08
• 危险品运输编号：
  UN 1189 3/PG 3
• 危险性描述：
  H226,H302 + H312 + H332,H360FD
• 危险性防范说明：
  P201,P280,P308 + P313
• 储存条件：
  储存时应注意以下事项： - 储存在阴凉、通风良好的仓库中。 - 远离火源和热源，库温不宜超过37℃。 - 保持容器密封。 - 应与氧化剂、酸类、碱类分开存放，切忌混存。 - 使用防爆型照明和通风设施。 - 禁止使用易产生火花的机械设备和工具。 - 储区应配备泄漏应急处理设备和合适的收容材料。

SDS

第一部分：化学品名称

制备方法与用途

用途：

• 用作纤维素脂、各种树脂、蜡和油的溶剂。

生产方法：精制方法为使用氯化钙、无水碳酸钠干燥后进行减压蒸馏。

类别：易燃液体

毒性分级：中毒

急性毒性：

• 大鼠口服 LD50: 3390 毫克/公斤
• 小鼠口服 LD50: 3100 毫克/公斤

刺激数据：

• 兔子眼睛 218 毫克 轻度

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，燃烧时产生刺激烟雾

储运特性：

• 库房需通风、低温干燥
• 需与氧化剂分开存放

灭火剂：干粉、二氧化碳、泡沫、1211 灭火剂

职业标准：

• TWA 120 毫克/立方米
• STEL 180 毫克/立方米

反应信息

• 作为反应物：
  描述：

  乙二醇甲醚乙酸酯 生成 乙烯基甲醚
  参考文献：
  名称：

  极性β-取代基在乙酸乙酯酯气相热解中的作用

  摘要：

  DOI：

  10.1021/j100446a002
• 作为产物：
  描述：

  乙二醇甲醚 以10%的产率得到
  参考文献：
  名称：

  DARODA R. J.; BLACKBOROW J. R.; WILKINSON G., J. CHEM. SOC. CHEM. COMMUN., 1980, NO 22, 1098-1100

  摘要：

  DOI：
• 作为试剂：
  描述：

  二碘甲烷 、 3,4-二氢-1-苯基萘 在 乙二醇甲醚乙酸酯 、 N-tert-butoxycarbonyl-L-valyl-L-proline methyl ester 、 diethylzinc 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以91%的产率得到7b-Phenyl-1,1a,2,3-tetrahydrocyclopropa[a]naphthalene
  参考文献：
  名称：

  [EN] ASYMMETRIC CYCLOPROPANATION
  [FR] CYCLOPROPANATION ASYMETRIQUE

  摘要：

  公开号：

  WO2005033050A3

文献信息

• Cyclopropanation of Olefins with Diazo Compounds Catalyzed by a Dicopper-substituted Silicotungstate [γ-H₂SiW₁₀O₃₆Cu₂(μ-1,1-N₃)₂]⁴⁻
  作者：Keigo Kamata、Toshihiro Kimura、Noritaka Mizuno

  DOI：10.1246/cl.2010.702

  日期：2010.7.5

  silicotungstate (TBA) 4 -[γ-H 2 SiW 10 O 36 Cu II 2 (μ-1,1-N 3 ) 2 ] (I, TBA = tetra-n-butylammonium) could act as an efficient precatalyst for the chemoselective cylopropanation of olefins with diazo compounds. Various kinds of olefins were efficiently converted to the corresponding cyclopropane derivatives in good yields.

  双铜取代的 γ-Keggin 硅钨酸盐 (TBA) 4 -[γ-H 2 SiW 10 O 36 Cu II 2 (μ-1,1-N 3 ) 2 ] (I, TBA = 四正丁基铵)作为烯烃与重氮化合物化学选择性环丙烷化的有效预催化剂。各种烯烃以良好的收率有效地转化为相应的环丙烷衍生物。
• A Method for Esterification Reaction Rate Prediction of Aliphatic Monocarboxylic Acids with Primary Alcohols in 1,4-Dioxane Based on Two Parametrical Taft Equation
  作者：Ján Vojtko、Peter Tomčík

  DOI：10.1002/kin.20845

  日期：2014.3

  concentrations reaction rate depends only on the structure of reactants and, therefore, can be predicted by a correlation equation with two Taft coefficients (inductive and steric effects). From these equations, it is possible to estimate the esterification reaction rate constant for other acid‐alcohol pairs. This methodology may also be suitable for other kinetic systems measured under comparable experimental

  研究了脂肪族一元羧酸与伯醇在1,4-二恶烷中作为惰性溶剂的酯化反应速率。在恒定体积的间歇式反应器中，在60°C的恒定温度，固定的离子强度和pH下，将酸与1-丙醇酯化，将醇与乙酸酯化作为模型反应物。为了评价反应速率，应用了平衡反应的精确动力学方程。在这些条件下，对于低反应物，浓度反应速率仅取决于反应物的结构，因此可以通过具有两个塔夫脱系数的相关方程（感应效应和空间效应）进行预测。从这些方程式，可以估计其他酸-醇对的酯化反应速率常数。
• Cross‐Dehydrogenative C−O Coupling of Oximes with Acetonitrile, Ketones and Esters
  作者：Zhen‐Yu Chen、Hua‐Ju Liang、Ri‐Xing Chen、Lei Chen、Xiang‐Zheng Tang、Ming Yan、Xue‐Jing Zhang

  DOI：10.1002/adsc.201900370

  日期：2019.7.11

  generation of radical intermediates via EDA complexes had been developed. This approach enables a cross‐dehydrogenative C−O coupling of oximes with acetonitrile, ketones and esters with high yields and regioselectivities. Perfluorobutyl iodide was used as the unique electron acceptor to trigger a new radical formation. The radical pathway was confirmed by UV‐Vis spectroscopy, radical inhibiting, trapping

  已经开发了一种无过渡金属的方法，用于通过EDA络合物生成自由基中间体。这种方法可以使肟与乙腈，酮和酯进行交叉脱氢的C-O偶联，具有高收率和区域选择性。全氟丁基碘被用作引发新的自由基形成的独特电子受体。自由基途径已通过UV-Vis光谱，自由基抑制，捕集和动力学实验得以证实。
• The chemistry of organoborates. 9. A regiospecific and highly stereoselective construction of trisubstituted αβ-unsaturated ketones, tetrasubstituted αβ-unsaturated ketones and specifically protected 1,3-diketones from alkynyltrialkylborates
  作者：Andrew Pelter、M. Eamon Colclough

  DOI：10.1016/0040-4020(94)00953-r

  日期：1995.1

  fashion such that the dioxolanium group and the migrating group are on the same side of the new alkene intermediate. Hydrolysis of the intermediate yields Z-trisubstituted αβ-unsaturated ketones in which all three substituents have different origins and can be independently varied. Oxidation of the intermediates gives β-ketoacetals, which are regiospecifically protected 1,3-diketones. If the initial intermediates

  炔基三烷基硼酸锂与氟磺酸二恶唑鎓盐以高度立体选择性的方式反应，使得二恶戊鎓基团和迁移基团在新的烯烃中间体的同一侧。中间体的水解产生Z-三取代的αβ-不饱和酮，其中所有三个取代基具有不同的起源并且可以独立地变化。中间体的氧化产生β-酮缩醛，它是区域特异性保护的1,3-二酮。如果允许初始中间体静置，则将发生另一种迁移，并导致四取代的αβ-不饱和酮。
• Indium triiodide catalysed one-step conversion of tetrahydropyranyl ethers to acetates with high selectivity
  作者：Brindaban C. Ranu、Alakananda Hajra

  DOI：10.1039/b100014b

  日期：——

  A very simple and efficient method has been developed for the chemoselective one-step conversion of tetrahydropyranyl ethers of primary alcohols to the corresponding acetates through an indium triiodide catalysed transesterification process in ethyl acetate.

  一种非常简单高效的方法被开发出来，可以通过在乙酸乙酯中以碘化铟为催化剂的转酯化过程，将初级醇的四氢吡喃醚选择性地一步转化为相应的醋酸酯。

表征谱图