2-chloro-1-methyl-1,3,2-oxazaphosphacyclopentane 2-oxide | 66046-61-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: 2-chloro-1-methyl-1,3,2-oxazaphosphacyclopentane 2-oxide
• 英文别名: 2-chloro-3-methyl-1,3,2-oxazaphosphacyclopentane-2-oxide；2-chloro-3-methyl-1-oxa-3-aza-2-phosphacyclopentane 2-oxide；2-chloro-3-methyl-[1,3,2]oxazaphospholidine 2-oxide；2-Chloro-3-methyl-1,3,2-oxazaphospholidine-2-oxide；2-chloro-3-methyl-1,3,2λ5-oxazaphospholidine 2-oxide
• CAS: 66046-61-5
• 化学式: C₃H₇ClNO₂P
• 分子量: 155.521
• InChiKey: GFFSAOAQJPCGPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 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：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  十二烷基伯胺 、 2-chloro-1-methyl-1,3,2-oxazaphosphacyclopentane 2-oxide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以100%的产率得到N-dodecyl-3-methyl-2-oxo-1,3,2lambda5-oxazaphospholidin-2-amine
  参考文献：
  名称：

  The Synthesis of Some N-Linked Phospholipid Analogues via Phosphorodiamidate Heterocyclic Intermediates

  摘要：

  新型 N-连接磷脂类似物是通过杂环磷酰二胺中间体高产制备的。例如，从 N-甲基乙醇胺制备 2-氯-1-甲基-1,3,2-噁磷杂环戊烷 2-氧化物，并与一系列（长链）伯胺或仲胺反应，得到环状磷酰二胺中间体，在酸性条件下使用甲醇或乙醇将其开环。在仲胺的情况下，我们寻找了中间体的替代途径，在某些情况下，得到了更好的产率。所有中间体和产物都通过高场多核（1H、13C、31P）核磁共振和质谱分析法进行了全面鉴定，它们可能具有有用的物理和生物化学特性。

  DOI：

  10.1055/s-1996-4398
• 作为产物：
  描述：

  N-甲基-2-羟基乙胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-chloro-1-methyl-1,3,2-oxazaphosphacyclopentane 2-oxide
  参考文献：
  名称：

  新型磷脂类似物的相行为。

  摘要：

  使用偏光显微镜研究了含有磷酰胺部分的磷脂类似物的相行为。观察到由层状和正常拓扑的六方相和中间相组成的复杂液晶多态性，并发现其取决于磷酰胺头基的结构及其甲基化。另外，在某些系统中，在相图的胶束溶液部分观察到较低的固相边界。比较了这些新型两亲物与季铵和低聚环氧乙烷两亲物的聚集行为。

  DOI：

  10.1016/0009-3084(94)02423-3

文献信息

• Studies on the urinary metabolites of isophosphamide and its activated species in rabbits.
  作者：AKIRA TAKAMIZAWA、TSUYOSHI IWATA、SAICHI MATSUMOTO

  DOI：10.1248/cpb.25.2900

  日期：——

  Investigations on the urinary metabolites of isophosphamide, 4-hydroxyisophosphamide and 4-hydroxyisophosphamide including stereoisomers of the C4-oxidized derivatives in rabbits revealed that their metabolic behaviors were different from each other and also form those of cyclophosphamide. Administration of isophosphamide to rabbits resulted in the urinary excretion of carboxyisophosphamide and two N-dechloroethylated metabolites besides considerable amount of unchanged isophosphamide, while 4-hydroxyisophosphamide was metabolized principally into carboxyisophosphamide. In the case of 4-hydroxyisophosphamide, carboxyisophosphamide was excreted as a major metabolite, but considerable amount of a new metabolite which might be produced from 4-ketoisophosphamide via a hitherto unknown pathway was also excreted besides small amount of 4-ketoisophosphamide. Mechanism of the formation of this new metabolite was proposed based on the chemical conversion of a suggested intermediate into the metabolite. PHosphorus configuration of the C4-oxidized isophosphamides was found to have no significant effect upon their metabolism. It was suggested that the results of the present studies could account for the great differences in in vivo antitumor activities between isophosphamide and its pre-activated derivatives and also between isophosphamide and cyclophosphamide.

  对兔子尿液中异磷酰胺、4-羟基异磷酰胺和 4-羟基异磷酰胺（包括 C4 氧化衍生物的立体异构体）代谢产物的研究表明，它们的代谢行为与环磷酰胺不同。兔子服用异磷酰胺后，除了排出大量未改变的异磷酰胺外，尿液中还会排出羧基异磷酰胺和两种 N-脱氯乙基代谢物，而 4-羟基异磷酰胺则主要代谢为羧基异磷酰胺。就 4-羟基异磷酰胺而言，羧基异磷酰胺是排出体外的主要代谢物，但除了少量的 4-酮异磷酰胺外，还排出了相当数量的新代谢物，这种新代谢物可能是由 4-酮异磷酰胺通过迄今未知的途径产生的。这种新的代谢物的形成机制是根据所建议的中间体向代谢物的化学转化而提出的。研究发现，C4-氧化异磷酰胺的 PHosphorus 构型对其代谢没有明显影响。有人认为，本研究的结果可以解释异磷酰胺及其活化前衍生物之间以及异磷酰胺与环磷酰胺之间体内抗肿瘤活性的巨大差异。
• Substituted thiazolidinyl esters of mineral acids
  申请人：Ciba-Geigy Corporation

  公开号：US04582841A1

  公开（公告）日：1986-04-15

  Compounds of the formula ##STR1## in which one of the symbols R.sub.1 and R.sub.2 represents an alkyl radical that has 3 or 4 carbon atoms and is unsaturated in the 2,3-position, and the other represents such a radical or lower alkyl, R.sub.3 and R.sub.4 each represents, independently of the other, hydrogen or methyl, and A represents a radical of the formula ##STR2## in which Z.sub.1, or each of Z.sub.2 and Z.sub.3 independently of the other, represents hydrogen or lower alkyl, or Z.sub.2 and Z.sub.3 together represent lower alkylene, each of R.sub.5 and R.sub.6, independently of the other, represents hydrogen, lower alkyl, halogenated lower alkyl, or lower alkenyl or R.sub.5 and R.sub.6 together represent lower alkylene that is optionally interrupted by oxygen, sulphur or by optionally substituted nitrogen, and X represents OR.sub.7 or NR.sub.8 R.sub.9 in which R.sub.7 represents hydrogen or lower alkyl and each of R.sub.8 and R.sub.9, independently of the other, represents hydrogen, lower alkyl, halogenated lower alkyl, or lower alkenyl or R.sub.8 and R.sub.9 together represent lower alkylene that is optionally interrupted by oxygen, sulphur or by optionally substituted nitrogen, or R.sub.6 together with R.sub.7 or R.sub.8 represents a lower alkylene group Alk, and salts of such compounds in which Z.sub.1, or Z.sub.3 and optionally also Z.sub.2, or R.sub.7 represent(s) hydrogen, exhibit tumor-inhibiting activities.

  式为##STR1##的化合物，其中R.sub.1和R.sub.2中的一个代表具有3或4个碳原子且在2,3位不饱和的烷基基团，另一个代表这样的基团或更低的烷基，R.sub.3和R.sub.4分别独立地代表氢或甲基，A代表式##STR2##的基团，在该式中，Z.sub.1或Z.sub.2和Z.sub.3中的每一个独立地代表氢或更低的烷基，或Z.sub.2和Z.sub.3一起代表更低的烷基，R.sub.5和R.sub.6中的每一个独立地代表氢，更低的烷基，卤代更低的烷基或更低的烯基，或R.sub.5和R.sub.6一起代表可以由氧、硫或者可选取代的氮中断的更低的烷基，X代表OR.sub.7或NR.sub.8R.sub.9，在该式中，R.sub.7代表氢或更低的烷基，R.sub.8和R.sub.9中的每一个独立地代表氢、更低的烷基、卤代更低的烷基或更低的烯基，或R.sub.8和R.sub.9一起代表可以由氧、硫或者可选取代的氮中断的更低的烷基，或R.sub.6与R.sub.7或R.sub.8一起代表更低的烷基Alk，以及这种化合物的盐，其中Z.sub.1或Z.sub.3并且可选取Z.sub.2或R.sub.7代表氢，表现出抑制肿瘤的活性。
• Euerby, Melvin R.; Partridge, Lynda Z.; Learmonth, Michele P., Journal of Chemical Research, Miniprint, 1987, # 3, p. 815 - 830
  作者：Euerby, Melvin R.、Partridge, Lynda Z.、Learmonth, Michele P.、Ball, Hayden L.、Gibbons, William A.

  DOI：——

  日期：——
• Jones, A. Stanley; McGuigan, Christopher; Walker, Richard T., Journal of the Chemical Society. Perkin transactions I, 1984, # 7, p. 1471 - 1474
  作者：Jones, A. Stanley、McGuigan, Christopher、Walker, Richard T.、Balzarini, Jan、Clercq, Eric de

  DOI：——

  日期：——
• The Synthesis of Some N-Linked Phospholipid Analogues via Phosphorodiamidate Heterocyclic Intermediates
  作者：Christopher McGuigan、Andrew Mackenzie

  DOI：10.1055/s-1996-4398

  日期：1996.11

  Novel N-linked phospholipid analogues have been prepared in high yield via heterocyclic phosphorodiamidate intermediates. Thus, 2-chloro-1-methyl-1,3,2-oxazaphosphacyclopentane 2-oxide was prepared from N-methylethanolamine and was allowed to react with a series of (long chain) primary or secondary amines to give cyclic phosphorodiamidate intermediates which could be ring opened using either methanol or ethanol under acidic conditions. In the case of secondary amines alternative routes to the intermediates were sought and, in some cases, gave preferable yields. All intermediates and products were fully characterised by high field multinuclear (1H, 13C, 31P) NMR and mass spectrometry and they may display useful physical and biochemical properties.

  新型 N-连接磷脂类似物是通过杂环磷酰二胺中间体高产制备的。例如，从 N-甲基乙醇胺制备 2-氯-1-甲基-1,3,2-噁磷杂环戊烷 2-氧化物，并与一系列（长链）伯胺或仲胺反应，得到环状磷酰二胺中间体，在酸性条件下使用甲醇或乙醇将其开环。在仲胺的情况下，我们寻找了中间体的替代途径，在某些情况下，得到了更好的产率。所有中间体和产物都通过高场多核（1H、13C、31P）核磁共振和质谱分析法进行了全面鉴定，它们可能具有有用的物理和生物化学特性。