dimethyl phosphonium cation | 133082-25-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl phosphonium cation
• 英文别名: Dimethyl phosphonate；dimethoxy(oxo)phosphanium
• CAS: 133082-25-4
• 化学式: C₂H₆O₃P
• 分子量: 109.042
• InChiKey: YLFBFPXKTIQSSY-UHFFFAOYSA-N

物化性质

• 物理描述：
  Dimethyl hydrogen phosphite is a colorless liquid. (USCG, 1999)
• 颜色/状态：
  Mobile, colorless liquid
• 气味：
  Mild odor
• 沸点：
  170.5 °C
• 熔点：
  -60.0 °C
• 闪点：
  70 °C (Closed cup)
• 溶解度：
  In water, >10 g/100 mL at 20 °C
• 密度：
  1.2002 g/cu cm at 20 °C
• 蒸汽密度：
  7.9 (Air = 1)
• 蒸汽压力：
  1.5 mm Hg at 20 °C
• 自燃温度：
  237 °C
• 分解：
  When heated to decomposition it emits toxic fumes of /phosphorous oxides/.
• 粘度：
  1.06 centistokes at 25 °C
• 折光率：
  Index of refraction: 1.4036 at 20 °C/D

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  6
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

ADMET

代谢

在体外，DMHP被肝脏、肺、肾脏、前胃和腺胃的微粒体组分代谢成甲醛。在体内，DMHP被代谢为脱甲基产物，单甲基氢磷酰（MMHP），并通过尿液排出。本研究的结果表明，NTP对DMHP进行的致癌性研究是在吸收、代谢和处置DMHP在两种物种中呈线性的剂量范围内进行的。

In vitro, DMHP was metabolized to formaldehyde by the microsomal fractions of liver, lungs, kidneys, forestomach, and glandular stomach. In vivo, DMHP was metabolized to the product of demethylation, monomethyl hydrogen phosphite (MMHP), which was excreted in urine. Results of this study indicate that the NTP carcinogenicity study with DMHP was carried out within the dose range in which the absorption, metabolism, and disposition of DMHP are linear in both species.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

评估：没有关于亚磷酸二甲酯致癌性的相关流行病学数据。在实验动物中亚磷酸二甲酯的致癌性证据有限。总体评估：亚磷酸二甲酯的致癌性对人不可分类（第3组）。

Evaluation: No epidemiological data relevant to the carcinogenicity of dimethyl hydrogen phosphite were available. There is limited evidence for the carcinogenicity of dimethyl hydrogen phosphite in experimental animals. Overall evaluation: Dimethyl hydrogen phosphite is not classifiable as to its carcinogenicity to humans (Group 3).

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

国际癌症研究机构致癌物：亚磷酸二甲酯

IARC Carcinogenic Agent:Dimethyl hydrogen phosphite

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构（IARC）致癌物分类：第3组：无法归类其对人类致癌性

IARC Carcinogenic Classes:Group 3: Not classifiable as to its carcinogenicity to humans

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构专著：第48卷：（1990年）一些阻燃剂和纺织化学品以及在纺织制造工业中的暴露

IARC Monographs:Volume 48: (1990) Some Flame Retardants and Textile Chemicals, and Exposures in the Textile Manufacturing Industry

来源:International Agency for Research on Cancer (IARC)

毒理性

• 暴露途径

这种物质可以通过吸入、皮肤接触和摄入被身体吸收。

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

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

吸收、分配和排泄

美国国家毒理学计划（NTP）对亚甲基氢磷酰（DMHP）的研究表明，通过口服灌胃的慢性给药导致Fischer 344大鼠的肺部和前胃新生物损伤的发生率增加，但在B6C3F1小鼠中并未出现。当前的研究旨在评估这种物种选择性的代谢基础，如果有的话，通过研究碳-14-DMHP在相应品系的大鼠和小鼠中的代谢和分布。这项研究的结果表明，以10-200 mg/kg的剂量范围给药的DMHP在大鼠和小鼠的胃肠道中被迅速且几乎完全吸收。DMHP衍生的放射性主要通过呼出的空气中的CO2排出，占44-57%，尿液占28-49%，而在粪便中收集的非常少，占1-2%，或作为挥发性有机物，占2-3%。DMHP衍生的放射性在大鼠和小鼠的组织中广泛分布，以肝脏、肾脏、脾脏、肺和前胃的浓度最高，而在大脑、骨骼肌和脂肪组织中的浓度最低。放射性从鼠组织中消失的速度大约是从大鼠组织中消失速度的两倍。在体外，DMHP通过肝脏、肺、肾脏、前胃和腺胃的微粒体组分代谢为甲醛。在体内，DMHP代谢为脱甲基产物，一甲基氢磷酰（MMHP），后者通过尿液排出。这项研究的结果表明，NTP对DMHP致癌性的研究是在DMHP的吸收、代谢和分布在线性范围内的剂量进行的。DMHP的代谢和分布的明显物种依赖性差异仅限于小鼠更快的代谢和消除。因此，DMHP致癌性的物种依赖性变化最可能是由于代谢和分布以外的因素。

A study of dimethyl hydrogen phosphite (DMHP) by the National Toxicology Program (NTP) indicated that chronic administration by oral gavage resulted in an increased incidence of neoplastic lesions in the lungs and forestomachs of Fischer 344 rats but not in B6C3F1 mice. The current study was designed to evaluate the metabolic basis, if any, of this species selectivity by studying the metabolism and disposition of carbon-14-DMHP in the respective strains of rats and mice. Results of this study indicate that DMHP administered at a range of dose of 10-200 mg/kg was readily and near completely absorbed from the gastrointestinal tracts of rats and mice. DMHP-derived radioactivity was eliminated primarily as CO2 in the expired air, 44-57%, and urine, 28-49%, and very little was collected in feces, 1-2%, or as volatile organics, 2-3%. DMHP-derived radioactivity was widely distributed in tissues of rats and mice, with the highest concentrations observed in the liver, kidneys, spleen, lungs, and forestomach, and the lowest in brain, skeletal muscle, and adipose tissue. The disappearance of radioactivity from mouse tissues was approximately twice as rapid as from rat tissues. In vitro, DMHP was metabolized to formaldehyde by the microsomal fractions of liver, lungs, kidneys, forestomach, and glandular stomach. In vivo, DMHP was metabolized to the product of demethylation, monomethyl hydrogen phosphite (MMHP), which was excreted in urine. Results of this study indicate that the NTP carcinogenicity study with DMHP was carried out within the dose range in which the absorption, metabolism, and disposition of DMHP are linear in both species. Apparent species-dependent differences in the metabolism and disposition of DMHP are limited to the more rapid metabolism and elimination by the mouse. Therefore, the species-dependent variations in the carcinogenicity of DMHP are most likely attributable to factors other than metabolism and disposition.

来源:Hazardous Substances Data Bank (HSDB)

反应信息

• 作为反应物：
  描述：

  dimethyl phosphonium cation 、 3-羟基异苯并呋喃-1(3H)-酮 以95的产率得到3-氧代-1,3-二氢异苯并呋喃-1-膦酸二甲酯
  参考文献：
  名称：

  Phthalazinone derivatives

  摘要：

  化合物的式子(I)：其中A和B表示一个可选取的取代的融合芳香环；X可以是NRX或CRXRY；如果X═NRX，则n为1或2，如果X═CRXRY，则n为1；RX从以下群组中选择：H，可选取的取代C1-20烷基，C5-20芳基，C3-20杂环基，酰胺，硫酰胺，酯，酰基和磺酰基；RY从H，羟基，氨基中选择；或者RX和RY可以一起形成螺环C3-7环烷基或杂环基；RC1和RC2都是氢，或者当X是CRXRY时，RC1，RC2，RX和RY与它们附着的碳原子一起可以形成一个可选取的取代的融合芳香环；R1从H和卤素中选择。

  公开号：

  US20050059663A1

文献信息

• PHTHALAZINONE DERIVATIVES
  申请人：Menear Keith Allan

  公开号：US20080146575A1

  公开（公告）日：2008-06-19

  4-[3-(4-cyclopropanecarbonyl-piperazine-1-carbonyl)-4-fluoro-benzyl]-2H-phthalazin-1-one as crystalline Form A.

  4-[3-(4-环丙烷羰基-哌嗪-1-羧酰)-4-氟苯基]-2H-邻菲啉-1-酮的结晶形式A。
• [EN] PHTHALAZINONE DERIVATIVES<br/>[FR] DERIVES DE PHTALAZINONE
  申请人：KUDOS PHARM LTD

  公开号：WO2004080976A1

  公开（公告）日：2004-09-23

  Compounds of the formula (I): wherein A and B together represent an optionally substituted, fused aromatic ring; X can be NRX or CRXRY; if X NRX then n is 1 or 2 and if X = CRXRY then n is 1; RX is selected from the group consisting of H, optionally substituted C1-20 alkyl, C5-20 aryl, C3-20 heterocyclyl, amido, thioamido, ester, acyl, and sulfonyl groups; RY is selected from H, hydroxy, amino; or RX and RY may together form a spiro-C3-7 cycloalkyl or heterocyclyl group; RC1 and RC2 are both hydrogen, or when X is CRX RY, RC1, RC2, RX and RY, together with the carbon atoms to which they are attached, may form an optionally substituted fused aromatic ring; and R1 is selected from H and halo.

  化合物的公式（I）：其中A和B一起表示一个可选择取代的融合芳香环；X可以是NRX或CRXRY；如果X是NRX，则n为1或2，如果X = CRXRY，则n为1；RX从H，可选择取代的C1-20烷基，C5-20芳基，C3-20杂环基，酰胺，硫酰胺，酯，酰基和磺酰基中选择；RY从H，羟基，氨基中选择；或者RX和RY可以一起形成螺旋C3-7环烷基或杂环基；RC1和RC2都是氢，或者当X是CRXRY时，RC1，RC2，RX和RY与它们连接的碳原子一起可以形成可选择取代的融合芳香环；R1从H和卤素中选择。
• Properties and reactions of trimethyl phosphite, trimethyl phosphate, triethyl phosphate, and trimethyl phosphorothionate by ion cyclotron resonance spectroscopy
  作者：Ronald V. Hodges、T. J. McDonnell、J. L. Beauchamp

  DOI：10.1021/ja00524a016

  日期：1980.2
• WO2008047082A2
  申请人：——

  公开号：——

  公开（公告）日：——
• Phthalazinone derivatives
  申请人：Martin Barr Niall Morrison

  公开号：US20050059663A1

  公开（公告）日：2005-03-17

  Compounds of the formula (I): wherein A and B together represent an optionally substituted, fused aromatic ring; X can be NR X or CR X R Y ; if X═NR X then n is 1 or 2 and if X═CR X R Y then n is 1; R X is selected from the group consisting of H, optionally substituted C 1-20 alkyl, C 5-20 aryl, C 3-20 heterocyclyl, amido, thioamido, ester, acyl, and sulfonyl groups; R Y is selected from H, hydroxy, amino; or R X and R Y may together form a spiro-C 3-7 cycloalkyl or heterocyclyl group; R C1 and R C2 are both hydrogen, or when X is CR X R Y , R C1 , R C2 , R X and R Y , together with the carbon atoms to which they are attached, may form an optionally substituted fused aromatic ring; and R 1 is selected from H and halo.

  化合物的式子(I)：其中A和B表示一个可选取的取代的融合芳香环；X可以是NRX或CRXRY；如果X═NRX，则n为1或2，如果X═CRXRY，则n为1；RX从以下群组中选择：H，可选取的取代C1-20烷基，C5-20芳基，C3-20杂环基，酰胺，硫酰胺，酯，酰基和磺酰基；RY从H，羟基，氨基中选择；或者RX和RY可以一起形成螺环C3-7环烷基或杂环基；RC1和RC2都是氢，或者当X是CRXRY时，RC1，RC2，RX和RY与它们附着的碳原子一起可以形成一个可选取的取代的融合芳香环；R1从H和卤素中选择。

表征谱图