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2,2,2-triethoxy-2,2-dihydro-5-methyl-1,2λ5-oxaphospholene | 131490-60-3

中文名称
——
中文别名
——
英文名称
2,2,2-triethoxy-2,2-dihydro-5-methyl-1,2λ5-oxaphospholene
英文别名
2,2,2-triethoxy-5-methyl-2,2,3,3-tetrahydro-1,2-oxaphosphole;2,2,2-triethoxy-1,2λ5-oxaphospholene;2,2,2-triethoxy-5-methyl-3H-1,2lambda5-oxaphosphole;2,2,2-triethoxy-5-methyl-3H-1,2λ5-oxaphosphole
2,2,2-triethoxy-2,2-dihydro-5-methyl-1,2λ<sup>5</sup>-oxaphospholene化学式
CAS
131490-60-3
化学式
C10H21O4P
mdl
——
分子量
236.248
InChiKey
HWDSITYQQHQWMI-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    1.9
  • 重原子数:
    15
  • 可旋转键数:
    6
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.8
  • 拓扑面积:
    36.9
  • 氢给体数:
    0
  • 氢受体数:
    4

反应信息

  • 作为反应物:
    描述:
    2,2,2-triethoxy-2,2-dihydro-5-methyl-1,2λ5-oxaphospholene 作用下, 以 四氯化碳 为溶剂, 反应 1.0h, 以90%的产率得到3-bromo-4-diethoxyphosphorylbutan-2-one
    参考文献:
    名称:
    α,β-functionalization of enones via pentacovalent oxaphospholenes
    摘要:
    2,2,2-Triethoxy-1,2-lambda-5-oxaphospholene, 1, reacts under mild, neutral conditions with bromine, dialkyl azodicarboxylates, and oxaziridines to produce beta-heteroatom substituted gamma-ketophosphonates and beta-acyl vinyl phosphonate in high yields.
    DOI:
    10.1016/s0040-4039(00)92373-6
  • 作为产物:
    参考文献:
    名称:
    通过五价氧代磷烯方法合成阿拉伯糖的 2-和 3-膦酰基甲基衍生物的方法
    摘要:
    概述了通过五价氧杂磷烯方法合成阿拉伯糖 2-和 3-膦酰基甲基衍生物的方法。必需的五共价氧杂磷烯与单保护的乙二醛衍生物或甘油醛缩酮的缩合具有高度立体选择性,在两种情况下都产生了作为主要异构体的合成羟醛产物。4a 还原为二醇并没有产生预期的立体选择性。5 和 6 的立体化学关联是通过碳酸盐。
    DOI:
    10.1080/10426509908546211
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文献信息

  • Synthetic Studies toward the Preparation of Phosphonate Analogs of Sphingomyelin and Ceramide 1-Phosphate Using Pentacovalent Organophospholene Methodology
    作者:Cynthia K. McClure、Pranab K. Mishra、Christopher W. Grote
    DOI:10.1021/jo962144v
    日期:1997.4.1
    pentacovalent oxaphospholene 3b (derived from methyl vinyl ketone and triethyl phosphite) readily condensed with dialkyl azodicarboxylates (R = Et, t-Bu, CH(2)CCl(3)) to form beta-hydrazido gamma-ketophosphonates 5 and 8 in excellent yields. Cleavage of the N-N bond in 5a (R = Et) or 5b (R = t-Bu) via standard methods was unsuccessful. Upon reduction with NaBH(4), 8 produced the oxazolidinone 9 (93%) as a diastereomeric
    描述了鞘磷脂和1-磷酸神经酰胺的膦酸酯类似物的合成的模型研究。五价氧杂腈3b(衍生自甲基乙烯基酮和亚磷酸三乙酯)容易与偶氮二羧酸二烷基酯(R = Et,t-Bu,CH(2)CCl(3))缩合以形成出色的β-基γ-酮膦酸酯5和8产量。通过标准方法在5a(R = Et)或5b(R = t-Bu)中切割NN键是不成功的。用NaBH(4)还原后,8生成3:1的恶唑烷酮9(93%)为非对映异构体混合物。在室温下用Zn / HOAc /丙酮处理9很容易使NN键断裂形成11(78-83%)。通过NOE实验确认11(3:1,反式:顺式)中的立体化学分配。
  • Direct synthesis of γ,γ-diketophosphonates from pentacovalent 1,2λ<sup>5</sup>-oxaphosphorane
    作者:Tae Woo Kim、Chung-Min Park、Kang-Yeoun Jung
    DOI:10.1080/10426507.2023.2198713
    日期:2023.10.3
    efficient procedure to prepare γ,γ-diketophosphonates via reactions between 1,2λ5-oxaphospholene and aromatic acid chlorides under mild conditions is proposed herein. The formation of the keto phosphonium ion of 1,2λ5-oxaphospholenes is favored at −10 °C, and these ions react with aromatic acid chlorides to yield γ,γ-diketophosphonates in 83–89% yields. This reaction may be readily applied for the preparation
    摘要 吡唑膦酸酯衍生物因其广泛的生物活性而在医药领域受到越来越多的关注。然而,作为α-吡唑膦酸酯前体的二酮膦酸酯的合成需要高温和过量的反应物才能进行。因此,本文提出了一种在温和条件下通过1,2λ 5-氧杂烯与芳香酰反应制备γ,γ-二酮膦酸盐的简单而有效的方法。1,2λ 5酮基离子的形成-10 °C 时有利于生成-氧杂烯,这些离子与芳香酰反应生成 γ,γ-二酮膦酸盐,产率为 83-89%。该反应可以很容易地应用于制备α-二酮膦酸酯的γ,γ-衍生物作为α-吡唑膦酸酯的前体,而α-吡唑膦酸酯是具有巨大医学意义的分子。
  • Dynamic equilibriums between pentavalent protonated oxyphosphoranes and their isomeric tetravalent enol phosphonium ions via inter- and intramolecular proton transfer
    作者:Marianne M. C. F. Castelijns、Pieter Schipper、Dirk Van Aken、Henk M. Buck
    DOI:10.1021/jo00314a010
    日期:1981.1
  • Pentacovalent oxaphosphorane chemistry in organic synthesis: a new route to substituted phosphonates
    作者:Cynthia K. McClure、Kang Yeoun Jung
    DOI:10.1021/jo00002a072
    日期:1991.1
  • Novel and efficient synthesis of uracil phosphonate derivatives via pentacovalent oxaphospholenes
    作者:Cynthia K. McClure、Christopher W. Grote、Arnold L. Rheingold
    DOI:10.1016/s0040-4039(00)77471-5
    日期:1993.2
    2,2,2-Triethoxy-1,2lambda5-oxaphospholene, 1, reacts under mild, neutral conditions with aryl isocyanates to produce the phosphonate-containing pyrimidinedione derivatives 2 and 3. X-ray structure determination of 3 confirmed its structure.
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同类化合物

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