2-amino-5,5-dimethyl-1,3,2-dioxaphosphorinan-2-oxide | 29727-88-6

• 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-amino-5,5-dimethyl-1,3,2-dioxaphosphorinan-2-oxide
• 英文别名: 5,5-dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-ylamine；1,3,2-Dioxaphospholan-2-amine, 5,5-dimethyl-, 2-oxide；5,5-dimethyl-2-oxo-1,3,2λ5-dioxaphosphinan-2-amine
• CAS: 29727-88-6
• 化学式: C₅H₁₂NO₃P
• 分子量: 165.129
• InChiKey: AHBQFWLPMLTOJK-UHFFFAOYSA-N

物化性质

• 沸点：
  328.2±9.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 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：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-5,5-dimethyl-1,3,2-dioxaphosphorinan-2-oxide 在 N-(chlorosulfinyl)imidazole 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到N-sulfinyl-2-oxo-5,5-dimethyl-1,3,2-dioxazaphosphoramidate
  参考文献：
  名称：

  Reactivity and Diastereoselectivity in the Thermal and Lewis Acid-Catalyzed Diels−Alder Reactions of N-Sulfinylphosphoramidates¹

  摘要：

  The [4 + 2] cycloaddition reactions of N-sulfinvlphosphoramidates, prepared from the corresponding phosphoramidates by treatment with N-(chlorosulfinyl)imidazole, and 1,3-cyclohexadiene were found to be diastereoselective in the absence (>90:10)and presence (>95:5) of Lewis acid. The sulfur configuration of the major adduct from the cycloaddition reaction has been established unambiguously by X-ray crystallography. The use of Lewis acids improved the diastereoselectivity and yield, as well as shortened reaction times. Based on the intermediacy of a tin chelate, and the absence of phosphoryl secondary orbital interactions, a mechanism for the cycloaddition reactions is discussed.

  DOI：

  10.1021/jo970186t
• 作为产物：
  描述：

  5,5-二甲基-2-氯-1,3,2-二氧磷杂己内酰磷酸酯 在 氨 作用下， 生成 2-amino-5,5-dimethyl-1,3,2-dioxaphosphorinan-2-oxide
  参考文献：
  名称：

  磷酸和硫代磷酸酯的烯酰胺。22. 酰基烯胺研究交流

  摘要：

  磷酸酯和硫代磷酸酯酰胺 (1a – c, 5) 与取代的乙醛 (3a – d) 反应形成烯酰胺 4a – h 和 6a – d。它们可以通过催化氢化转化为 N-取代的磷酸酯酰胺 (7a, b)，并通过与醛 (3b, d) 反应转化为 3- 氮杂戊二烯 (12a, b)。

  DOI：

  10.1002/ardp.19723050702

文献信息

• Stereoselective Synthesis of Nipecotic Acid Derivatives via Palladium-Catalyzed Decarboxylative Cyclization of γ-Methylidene-δ-valerolactones with Imines
  作者：Ryo Shintani、Masataka Murakami、Tamio Hayashi

  DOI：10.1021/ol802569q

  日期：2009.1.15

  A new synthetic method of multisubstituted nipecotic acid (piperidine-3-carboxylic acid) derivatives has been developed by way of palladium-catalyzed decarboxylative cyclization of γ-methylidene-δ-valerolactones with imines. By employing the diethoxyphosphinoyl group as the N-protecting group for imines, the reaction proceeds smoothly with high diastereoselectivity. The products thus obtained can be

  通过亚胺与钯催化的γ-亚甲基-δ-戊内酯的脱羧环化反应，开发了一种新的多取代的庚二酸（哌啶-3-羧酸）衍生物的合成方法。通过将二乙氧基膦酰基作为亚胺的N-保护基，反应以高的非对映选择性平稳地进行。由此获得的产物可以在简单的反应条件下进一步高效地衍生化。
• N,N-Dihalophosphoramides—VI
  作者：S. Zawadzki、A. Zwierzak

  DOI：10.1016/s0040-4020(01)93296-x

  日期：1973.1

  O,O′-Dialkyl N,N-dibromophosphoroamidates, a novel pseudohalogen-type reagent has been prepared by direct bromination of O,O′-dialkyl phosphoroamidates in aqueous potassium carbonate. The preparative usefulness of these compounds in the synthesis of N-phosphorylated 2-phenylaziridines has been demonstrated.

  O，O′-二烷基N，N-二溴代磷酰胺基酸酯，通过在碳酸钾水溶液中直接溴化O，O′-二烷基磷酰胺基酯，制备了一种新型的假卤素型试剂。已经证明这些化合物在N-磷酸化的2-苯基氮丙啶的合成中的制备用途。
• N,N-dihalophosphoramides—I
  作者：A. Zwierzak、A. Koziara

  DOI：10.1016/s0040-4020(01)92931-x

  日期：1970.1

  Diethyl N,N-dichlorophosphoroamidate (DCPA), a stable, easily distillable, but very reactive pseudo-halogen containing phosphorus has been prepared in excellent yield by direct chlorination of diethyl phosphoroamidate in buffered aqueous acid solution. The reaction was found to be of general use for the preparation of some structural analogues of DCPA.

  通过在缓冲的酸性水溶液中直接氯化氨基磷酸二乙酯，可以以优异的收率制备出稳定，易于蒸馏但反应性很强的含磷的N，N-二氯氨基磷酸二乙酯（DCPA）。发现该反应通常用于制备DCPA的一些结构类似物。
• Brault,J.-F. et al., Bulletin de la Societe Chimique de France, 1973, p. 3149 - 3153
  作者：Brault,J.-F. et al.

  DOI：——

  日期：——