methyloxirane | 16033-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: methyloxirane
• 英文别名: Propylene oxide；2-methyloxirane；1,2-epoxypropane；epoxypropane；propylene epoxide；1,2-propylene oxide；(±)-propylene oxide；rac-propylene oxide；propene oxide
• CAS: 16033-71-9
• 化学式: C₃H₆O
• mdl: MFCD00005126
• 分子量: 58.08
• InChiKey: GOOHAUXETOMSMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  4
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

环氧丙烷在中性pH下与DNA反应，生成两个主要产物，即N-7-(2-羟基丙基)鸟嘌呤和N-3-(2-羟基丙基)腺嘌呤。

PROPYLENE OXIDE REACTS WITH DNA AT NEUTRAL PH TO YIELD TWO PRINCIPAL PRODUCTS, N-7-(2-HYDROXYPROPYL)GUANINE & N-3-(2-HYDROXYPROPYL)ADENINE.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在一家生产烷基淀粉的工厂中，对暴露于环氧丙烷的工人的淋巴细胞进行了染色体畸变和微核的测量，同时也对与医疗器械消毒相关的环氧乙烷暴露工人进行了测量。血红蛋白中的加合物水平被用来确定两种化合物的体内剂量。环氧丙烷暴露工人的羟丙基缬氨酸水平与估计的暴露剂量相关。未暴露组中这种加合物的水平接近于检测方法的检测限。环氧丙烷暴露组中记录的羟乙基缬氨酸水平与早期关于职业未暴露受试者血红蛋白烷基化的数据一致。加合物测量结果显示，两组环氧乙烷暴露工人（即低暴露的装配工和高暴露的消毒工）的羟乙基缬氨酸水平升高，符合预期的是，这两个亚组的加合物水平不同。细胞遗传学研究的结果显示，环氧丙烷的致裂变潜力低于环氧乙烷，因为尽管最后一组的加合物水平较低，但环氧丙烷暴露个体的微核和染色体断裂频率低于装配工。

Chromosomal aberrations and micronuclei in lymphocytes were measured in workers exposed to propylene oxide in a factory alkylated starch, and in workers exposed to ethylene oxide in connection with sterilization of medical equipment. Adduct levels in hemoglobin were determined as a measure of in vivo doses of the two compounds. The levels of hydroxypropylvaline in propylene oxide-exposed workers were correlated in estimated exposure doses. The levels of this adduct in the unexposed group were close to the detection limit of the method. The levels of hydroxyethylvaline, recorded in the propylene oxide-exposed group were consistent with earlier data on hemoglobin alkylation in occupationally unexposed subjects. The adduct measurements revealed increased levels of hydroxyethylvaline in the two subgroups of ethylene oxide-exposed workers, ie, assemblers with a low and sterilizers with a high exposure. According to expectation the subgroups differed in adduct levels. The results of cytogenetic study showed that the clastogenic potency of propylene oxide was lower than that of ethylene oxide, since the propylene oxide-exposed individuals had lower frequencies of micronuclei and chromosomal breaks compared to the assemblers despite a lower adduct level in the last group.

来源:Hazardous Substances Data Bank (HSDB)

代谢

聚丙烯及其活性代谢物环氧丙烷在大鼠体内的药代动力学进行了评估，以检查两种化合物在致癌性方面的所谓差异。斯普拉格-道利大鼠分组在封闭式暴露系统中暴露于丙烯或环氧丙烷。药代动力学参数由双室模型确定，该模型用于计算吸入丙烯后产生的环氧丙烷的身体负担。整个身体与空气比例的热力学平衡常数取决于物质的物理性质，确定为丙烯为1.6，环氧丙烷为45。根据米氏常数，发现丙烯具有饱和动力学；相比之下，在暴露室的空气中初始浓度高达3000 ppm时，环氧丙烷没有观察到饱和动力学。通过药代动力学参数，计算了在连续暴露于环氧丙烷或丙烯的不同条件下环氧丙烷的身体负担。如果大鼠即使在高浓度下暴露于丙烯，环氧丙烷的最大身体负担也不会超过每毫升组织71纳升环氧丙烷气体的浓度。

The pharmacokinetics of propylene and its reactive metabolite, propylene oxide, were assessed in rats to examine purported differences in carcinogenicity between the two compounds. Groups of Sprague-Dawley rats were exposed in closed exposure systems to propylene or propylene oxide. Pharmacokinetic parameters were determined by a two compartment model which was used to calculate the body burden of propylene oxide resulting from inhaled propylene. The thermodynamic equilibrium constant for the whole body to air ratio was dependent on the physical properties of the substances and was determined to be 1.6 for propylene and 45 for propylene oxide. Saturation kinetics according to the Michaelis Menten constant were found for propylene; in contrast, no saturation kinetics were observed for propylene oxide up to initial concentrations of 3000 ppm in the atmosphere of the exposure chambers. By means of pharmacokinetic parameters, the body burden of propylene oxide was calculated for different conditions of continous exposure either to propylene oxide or to propylene. The maximum body burden of propylene oxide did not exceed a concentration of 71 nanoliters propylene oxide gas per milliter tissue if rats were exposed to propylene even at very high concentrations.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

癌症分类：B2组可能的人类致癌物

Cancer Classification: Group B2 Probable Human Carcinogen

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

分类：B2；可能的人类致癌物。分类依据：基于不充分的人类数据和两种动物接触部位在皮下注射、吸入和灌胃暴露时良性及恶性肿瘤发生率增加的情况。还有证据显示在多种测试系统中具有诱变性。环氧丙烷的结构与其他在动物中显示致癌活性的化学品相似。人类致癌性数据：不充分。动物致癌性数据：充分。

CLASSIFICATION: B2; probable human carcinogen. BASIS FOR CLASSIFICATION: Based on inadequate human data and an increased incidence of benign and malignant tumors at the site of exposure in two species of animals, when exposed by subcutaneous injection, by inhalation, and by gavage. There was also evidence of mutagenicity in a variety of test systems. Propylene oxide is structurally similar to other chemicals that demonstrate carcinogenic activity in animals.HUMAN CARCINOGENICITY DATA: Inadequate. ANIMAL CARCINOGENICITY DATA: Sufficient.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

评估：对于环氧丙烷对人类致癌性的证据不足。对于环氧丙烷对实验动物致癌性的证据是充分的。总体评估：环氧丙烷可能对人类具有致癌性（2B组）。

Evaluation: There is inadequate evidence in humans for the carcinogenicity of propylene oxide. There is sufficient evidence in experimental animals for the carcinogenicity of propylene oxide. Overall evaluation: Propylene oxide is possibly carcinogenic to humans (Group 2B).

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

A3：已确认的动物致癌物，对人类的相关性未知。

A3: Confirmed animal carcinogen with unknown relevance to humans.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

1,2-环氧丙烷：合理预期为人类致癌物。

1,2-Propylene Oxide: reasonably anticipated to be a human carcinogen.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

呼吸系统是吸收的主要途径，尽管皮肤也代表了一个生理上重要的物质进入身体的途径...。

THE RESPIRATORY SYSTEM IS THE PRIMARY ROUTE OF ABSORPTION, ALTHOUGH THE SKIN ALSO REPRESENTS A ROUTE BY WHICH PHYSIOLOGICALLY SIGNIFICANT AMT ... MAY ENTER THE BODY ... .

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 储存条件：
  | 2-8°C |

反应信息

• 作为反应物：
  描述：

  methyloxirane 在 chromium(III) oxide 、 氨 作用下， 生成 丙腈
  参考文献：
  名称：

  US2557703

  摘要：

  公开号：
• 作为产物：
  描述：

  丙烷 在 vanadium oxide supported on mesoporous SBA-3 silica 作用下， 生成 methyloxirane
  参考文献：
  名称：

  在二氧化硅负载的氧化钒上用氧气和/或一氧化二氮环氧化丙烷

  摘要：

  已经使用不同的氧化剂（一氧化二氮、氧气及其混合物）在 673-773 K 的温度范围内研究了丙烷到氧化丙烯 (PO) 在 SBA-3 结构的含 V 介孔二氧化硅上的氧化。 电子自旋共振光谱，紫外线– 可见光谱和 X 射线光电子能谱 (XPS)，以及 X 射线衍射、氢程序升温还原 (H 2 TPR) 和低温 N 2吸附/解吸，用于表征新鲜和废催化剂。XPS 光谱和 H 2 TPR 曲线显示，由于丙烷用 N 2氧化，V 物种显着减少单独的 O，导致丙烷转化率和 PO 的时空产率 (STY) 均降低。使用 N 2 O-氧混合物作为丙烷的氧化剂可使钒价稳定在与初始样品相似的水平，这导致随着运行时间的推移活性稳定。丙烷转化率为 40%，丙烯选择性为 45%，环氧丙烷选择性为 11%，对应于约 15 g kg cat -1 h -1的环氧丙烷的 STY ，这使得这些结果非常有希望相比与文献报道的数据。尽管

  DOI：

  10.1016/j.jcat.2021.09.022
• 作为试剂：
  描述：

  2,2-双(3-氨基-4-羟基苯基)六氟丙烷 、 4-(氨基甲基)苯甲酰氯 在 methyloxirane 、 5%-palladium/activated carbon 、 氢气 作用下， 以 丙酮 、 乙二醇乙醚 为溶剂， 生成
  参考文献：
  名称：

  KR20240079793A

  摘要：

  公开号：

文献信息

• Aminimides derived from <i>p</i> -substituted benzoylformic acid ester as thermal/photolatent bases and photoradical initiators
  作者：Manabu Kirino、Ikuyoshi Tomita

  DOI：10.1002/pola.26838

  日期：2013.10

  were synthesized from 1,1‐dimethylhydrazine, propylene oxide, and p‐substituted benzoylformic acid ester, respectively, and their activity as thermal/photolatent bases and photoradical initiators was studied in detail. Their thermal decomposition activity increased by the electron‐donating substituents on the benzene ring, being in order of 1a (p‐NMe2) > 1b (p‐MeO) > BFI (H) > 1c (p‐NO2). Photolysis

  1,1-二甲基-1-（2-羟丙基）胺苯甲酰基甲酰亚胺的衍生物（BFI和1a-c）分别由1,1-二甲基肼，环氧丙烷和对位取代的苯甲酰基甲酸酯合成，其活性为详细研究了热/光潜碱和光自由基引发剂。它们的热分解活性通过苯环上的供电子取代基增加，顺序为1a（p- NMe 2）> 1b（p- MeO）> BFI（H）> 1c（p- NO 2）。光解活性也受到取代基的影响，顺序如下：1b> BFI> 1a> 1c。通过使用氨基酰亚胺作为潜在的引发剂，进行了环氧化物/硫醇体系的热和光诱导碱催化聚合，以及乙烯基单体甲基丙烯酸2-羟乙酯的光自由基聚合。它们作为热碱和光碱/自由基引发剂的活性可以分别与它们的热分解和光解活性相关。©2013 Wiley Periodicals，Inc. J. Polym。科学，A部分：Polym。化学 2013，51，4292–4300
• Synthesis of Spiroacetal Pheromones via Metalated Hydrazones
  作者：Dieter Enders、Walter Dahmen、Eleonore Dederichs、Winfried Gatzweiler、Peter Weuster

  DOI：10.1055/s-1990-27080

  日期：——

  The synthesis of simple alkyl substituted spiroacetals by α,α′-alkylation of metalated acetone dimethylhydrazone with appropriate electrophiles and subsequent acid catalyzed cleavage and ring closure of the products is described.

  通过合适的亲电试剂与金属化丙酮二甲基脲的α,α′-烷基化反应，随后进行酸催化的断裂和环化闭合，描述了简单烷基取代螺缩醛的合成方法。
• Transition metal complexes in organic synthesis, part 43. First total synthesis of the free radical scavenger (±)-neocarazostatin B via iron- and nickel-mediated coupling reactions
  作者：Hans-Joachim Knölker、Wolfgang Fröhner、Alfred Wagner

  DOI：10.1016/s0040-4039(98)00527-9

  日期：1998.5

  The first total synthesis of the naturally occurring free radical scavenger (±)-neocarazostatin B is described by using a one-pot iron-mediated construction of the carbazole skeleton and a nickle-mediated prenylation as the key-steps.

  通过使用一锅铁介导的咔唑骨架结构和raz介导的烯丙基化作为关键步骤，描述了自然产生的自由基清除剂（±）-neocarazostatin B的第一个全合成。
• Asymmetric hydrolytic kinetic resolution with recyclable polymeric Co(<scp>iii</scp>)–salen complexes: a practical strategy in the preparation of (S)-metoprolol, (S)-toliprolol and (S)-alprenolol: computational rationale for enantioselectivity
  作者：Tamal Roy、Sunirmal Barik、Manish Kumar、Rukhsana I. Kureshy、Bishwajit Ganguly、Noor-ul H. Khan、Sayed H. R. Abdi、Hari C. Bajaj

  DOI：10.1039/c4cy00594e

  日期：——

  epoxide (up to 46% compared to 50% theoretical yield) along with high enantioselectivity (up to 99%) were obtained in most cases using catalyst 1. Further studies showed that catalyst 1 could retain its catalytic activity for six cycles under the present reaction conditions without any significant loss in activity or enantioselectivity. To show the practical applicability of the above synthesized catalyst

  合成了一系列基于许多非手性和手性连接基的手性聚合Co（III）-salen配合物，并在末端环氧化物的不对称水解动力学拆分中评估了它们的催化性能。明智地研究了该连接基的作用，发现在手性BINOL型聚合物Salen配合物1的情况下，未反应的环氧化物的催化剂反应性和对映选择性的增加，特别是在短和短的情况下。长链脂族环氧化物。在大多数情况下，使用催化剂1可获得良好的分离度，即未反应的环氧化物的收率高（高达50％的理论收率的46％），以及高对映选择性（高达99％）。进一步的研究表明，催化剂在当前的反应条件下，图1所示的催化剂可以保持其催化活性六个循环而没有任何活性或对映选择性的明显损失。为了显示上述合成催化剂的实际适用性，我们使用配合物1以中等收率和高对映选择性合成了一些有效的手性β-阻滞剂。DFT（M06-L / 6-31 + G ** // ONIOM（B3LYP / 6-31G *：STO-3
• Selective reduction of 2,4-dinitro- and 4,5-dinitroimidazole derivatives using iron dust
  作者：Dorota Olender、Justyna Żwawiak、Lucjusz Zaprutko

  DOI：10.1002/jhet.418

  日期：——

  5‐dinitroimidazoles have been selectively reduced to the corresponding aminonitroimidazole derivatives, using iron dust in glacial acetic acid at room temperature. 2,4‐Dinitroimidazoles have been reduced to the 2‐amino‐4‐nitro‐derivatives only but 4,5‐dinitroimidazoles have given 4‐amino‐5‐nitro‐ or 5‐amino‐4‐nitro‐ derivatives depended on the structure of the N‐substituent. J. Heterocyclic Chem., (2010).

  在室温下，使用冰醋酸中的铁粉将一系列N取代的2,4-二硝基咪唑，4,5-二硝基咪唑和2-甲基-4,5-二硝基咪唑选择性还原为相应的氨基硝基咪唑衍生物。2,4-二硝基咪唑仅被还原为2-氨基-4-硝基衍生物，但是4,5-二硝基咪唑根据结构的不同给出了4-氨基-5-硝基或5-氨基-4-硝基衍生物。的ñ -取代。J.杂环化​​学。（2010）。

表征谱图