dimethyl (1-methylethyl) phosphite | 52956-34-0

• 分子结构分类: 有机化合物 - 有机磷化合物 - 亚磷酸三烷基酯
• 英文名称: dimethyl (1-methylethyl) phosphite
• 英文别名: Dimethyl (2-oxopropyl)phosphonate；Phosphorigesaeure-dimethylisopropylester；Dimethyl propan-2-yl phosphite
• CAS: 52956-34-0
• 化学式: C₅H₁₃O₃P
• 分子量: 152.13
• InChiKey: TZUGELZQOLSLAD-UHFFFAOYSA-N

物化性质

• 沸点：
  118.1±9.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dimethyl (1-methylethyl) phosphite 、 碘甲烷 反应 1.0h， 以79%的产率得到isopropyl methyl methylphosphonate
  参考文献：
  名称：

  Bisphosphonic Compounds. II. Preparation of Monophosphonic Starting Materials. Mixed Esters of Methylphosphonic Acid

  摘要：

  Methyl (1-methylethyl) methylphosphonate was obtained from PCl3 via (Pr(i)O)PCl2 and (Pr(i)O)P(OMe)2 followed by the Michaelis-Arbuzov reaction with Mel. The yield was 79 % with 95 % chemical purity. Less reasonable conversions were obtained for some related mixed diesters.

  DOI：

  10.1080/00397919208021302
• 作为产物：
  描述：

  N,N-二异丙基亚膦酸二甲酯酰胺 、 异丙醇 在 四氮唑 作用下， 以 乙腈 为溶剂， 以90%的产率得到dimethyl (1-methylethyl) phosphite
  参考文献：
  名称：

  Site-specific functionalisation of proteins by a Staudinger-type reaction using unsymmetrical phosphites

  摘要：

  非对称亚磷酸盐与对叠氮苯丙氨酸发生高效的斯陶丁格反应，可用于蛋白质的生物素化，从而扩大了芳基叠氮化物与对称亚磷酸盐发生化学选择性斯陶丁格-亚磷酸盐反应生成相应磷酰胺酸盐的范围。

  DOI：

  10.1039/b926818a

文献信息

• Organophosphorus chemistry. Part 1. The synthesis of alkyl methylphosphonic acids
  作者：Christopher M. Timperley、Michael Bird、Ian Holden、Robin M. Black

  DOI：10.1039/b007077g

  日期：——

  Several alkyl hydrogen methylphosphonates of structure RO(HO)P(O)Me were synthesised by a three-stage route [R = i-Pr, n-Bu, i-Bu, s-Bu, pinacolyl Me3C-CH(Me)-, cyclopentyl and cyclohexyl]. Trimethyl phosphite was transesterified with alcohols in the presence of sodium catalyst to give the mixed phosphites (MeO)2POR in 6–64% yield. Treatment of these with methyl iodide gave alkyl methyl methylphosphonates

  通过三步路线合成了结构RO（HO）P（O）Me的几种烷基氢甲基膦酸酯[R =  i -Pr，n -Bu，我-Bu，s -Bu，pinacolyl Me 3 C-CH（Me）-，环戊基 和 环己基]。 亚磷酸三甲酯 被酯交换 酒类 在钠存在下 催化剂得到6–64％的混合亚磷酸酯（MeO）2 POR。用这些治疗甲基碘以66–95％的收率得到烷基甲基甲基膦酸酯RO（MeO）P​​（O）Me。可选择的脱甲基 这些化合物的 溴三甲基硅烷， 其次是 甲醇分解甲硅烷基磷酯RO（Me 3 SiO）P（O）Me生成氢膦酸酯 收率为60–97％。
• Synthesis of Some Guanylhydrazones and Imidazolinylhydrazones as Thromboxane-Synthase and Platelet Aggregation Inhibitors
  作者：N. Desideri、I. Sestili、P. Piccardoni、S. Rotondo、C. Cerletti、M. L. Stein

  DOI：10.1002/ardp.19923251206

  日期：——

  The imidazolinylhydrazones of (3‐pyridinyloxy)‐acetaldehyde and of 6‐[3‐(2‐formyl‐pyridinyl)oxy]hexanoic acid were synthesized as cyclic analogues of the corresponding guanylhydrazones which were found to be selective inhibitors of human thromboxane‐synthase. The benzene isosters were also prepared in order to define the importance of the ring nitrogen for the activity.‐ Moreover, the guanyl‐ and

  (3-吡啶基氧基)-乙醛和6-[3-(2-甲酰基-吡啶基)氧基]己酸的咪唑啉腙被合成为相应脒腙的环状类似物，它们被发现是人血栓素合酶的选择性抑制剂。为了确定环氮对活性的重要性，还制备了苯等排体。此外，两个 6 - [(3-吡啶基) 氧基] 己酸的鸟苷和咪唑啉腙在 2 位烷基链中显示为制备了α，β-不饱和酮功能。咪唑啉腙7和18是血栓烷合成酶的选择性抑制剂，而两种不影响前列腺素生物合成的脒腙14和15似乎是血栓烷受体的拮抗剂。
• Phosphitylation via the Mitsunobu reaction
  作者：I.Darren Grice、Peta J. Harvey、Ian D. Jenkins、Michael J. Gallagher、Millagahamada G. Ranasinghe

  DOI：10.1016/0040-4039(95)02282-1

  日期：1996.2

  Treatment of a dialkyl phosphite with triphenylphosphine and diisopropyl azodicarboxylate in toluene, followed by addition of an alcohol, results in the formation of the corresponding trialkyl phosphite. Similarly, dialkyl phosphonites can be synthesised from monoalkyl phosphites (alkyl phosphinates).

  用三苯基膦和偶氮二羧酸二异丙酯在甲苯中处理亚磷酸二烷基酯，然后加入醇，导致形成相应的亚磷酸三烷基酯。类似地，二烷基亚膦酸酯可以由亚磷酸单烷基酯（亚膦酸烷基酯）合成。
• DE2039529
  申请人：——

  公开号：——

  公开（公告）日：——
• Site-specific functionalisation of proteins by a Staudinger-type reaction using unsymmetrical phosphites
  作者：Verena Böhrsch、Remigiusz Serwa、Paul Majkut、Eberhard Krause、Christian P. R. Hackenberger

  DOI：10.1039/b926818a

  日期：——

  Unsymmetrical phosphites react efficiently in a Staudinger reaction with p-azido-phenylalanine, which can be applied for the biotinylation of proteins, thereby expanding the scope of the chemoselective Staudinger-phosphite reaction of aryl azides with symmetrical phosphites to the corresponding phosphoramidates.

  非对称亚磷酸盐与对叠氮苯丙氨酸发生高效的斯陶丁格反应，可用于蛋白质的生物素化，从而扩大了芳基叠氮化物与对称亚磷酸盐发生化学选择性斯陶丁格-亚磷酸盐反应生成相应磷酰胺酸盐的范围。