dimethyl [2-(methoxy(methyl)amino)-2-oxoethyl]phosphonate | 134833-70-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: dimethyl [2-(methoxy(methyl)amino)-2-oxoethyl]phosphonate
• 英文别名: 2-dimethoxyphosphoryl-N-methoxy-N-methylacetamide
• CAS: 134833-70-8
• 化学式: C₆H₁₄NO₅P
• 分子量: 211.155
• InChiKey: HENULVZEKKXLBD-UHFFFAOYSA-N

物化性质

• 沸点：
  262.9±42.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl [2-(methoxy(methyl)amino)-2-oxoethyl]phosphonate 、 β-四氢萘酮 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 乙腈 为溶剂， 反应 108.0h， 以96%的产率得到3,4-dihydro-N-methoxy-N-methyl-2-naphthaleneacetamide
  参考文献：
  名称：

  Enynones in Organic Synthesis. 8. Synthesis of the Antimicrobial-Cytotoxic Agent Juncusol and Members of the Effusol Class of Phenols

  摘要：

  Two new syntheses of phenols have been developed which have been utilized in an efficient preparation of the antimicrobial-cytotoxic agent juncusol (22) and several members of the effusol (23) class of phenols. These results complement our earlier studies with enynones of type 42 and provide for the highly efficient conversion of 42 to either methylenecyclopentenones 45 or phenols of type 47 or 54 with virtually 100% selectivity.

  DOI：

  10.1021/jo00107a017
• 作为产物：
  描述：

  2-溴-N-甲氧基-N-甲基乙酰胺 、 三甲氧基磷 生成 dimethyl [2-(methoxy(methyl)amino)-2-oxoethyl]phosphonate
  参考文献：
  名称：

  juncusol的新型合成

  摘要：

  Juncusol（7）已通过新颖的电环化工艺从已知的β-四氢萘酮衍生物9开始制备。

  DOI：

  10.1016/s0040-4039(00)79645-6

文献信息

• Toward the total synthesis of phorboxazole A: synthesis of an advanced C4–C32 subunit using the Jacobsen hetero Diels–Alder reaction
  作者：Ian Paterson、Chris A. Luckhurst

  DOI：10.1016/s0040-4039(03)00754-8

  日期：2003.5

  The tetrahydropyranone 3, representing a pentacyclic C4–C32 segment of the phorboxazoles, was obtained by a complex hetero Diels–Alder (HDA) coupling performed between the 2-siloxydiene 23 and the oxazole aldehyde 4, mediated by the chiral tridentate Cr(III) catalyst 14. In preliminary studies, the tetrahydropyrans 17, 33 and 35 were accessed using this same asymmetric HDA methodology with varying

  的四氢吡喃酮3，代表五环ç 4 -C 32段所述的phorboxazoles，用复杂的杂狄尔斯-阿尔德（HDA）2- siloxydiene之间进行耦合而获得23和恶唑醛4，通过手性三齿的Cr（介导的III）催化剂14。在初步研究中，四氢吡喃17，33和35使用具有不同的立体选择性此相同的非对称HDA方法被访问。
• A Synthesis of the Carbocyclic Core of Maoecrystal V
  作者：Kiel E. Lazarski、Dennis X. Hu、Charlotte L. Stern、Regan J. Thomson

  DOI：10.1021/ol101025r

  日期：2010.7.2

  An approach toward the synthesis of the complex polycyclic diterpene maoecrystal V (1) is described. Construction of the advanced tetracyclic core structure (i.e., 19) was achieved in 13 steps from 3,3-dimethylcyclohexanone (6) by employing a stereoselective Nazarov cyclization followed by a Diels−Alder reaction to forge the two contiguous quaternary stereocenters.

  描述了一种合成复杂的多环二萜微晶 V ( 1 ) 的方法。高级四环核心结构（即19）的构建是从 3,3-二甲基环己酮（6）通过立体选择性 Nazarov 环化和 Diels-Alder 反应以形成两个连续的四元立体中心的13 个步骤实现的。
• Catalytic Intramolecular Conjugate Additions of Aldehyde-Derived Enamines to α,β-Unsaturated Esters
  作者：Zebediah C. Girvin、Philip P. Lampkin、Xinyu Liu、Samuel H. Gellman

  DOI：10.1021/acs.orglett.0c01666

  日期：2020.6.5

  enamines to α,β-unsaturated esters. Despite extensive prior exploration of conjugate additions of aldehyde-derived enamines, catalytic conjugate additions to unactivated enoate esters are unprecedented. Achieving enantioselective and diastereoselective six-membered ring formation requires the coordinated action of a chiral pyrrolidine, for nucleophilic activation of the aldehyde via enamine formation, and

  我们报告了一对已知的催化剂，使醛衍生的烯胺分子内共轭加成到 α,β-不饱和酯。尽管之前对醛衍生的烯胺的共轭加成进行了广泛的探索，但未活化的烯酸酯的催化共轭加成是前所未有的。实现对映选择性和非对映选择性六元环的形成需要手性吡咯烷的协调作用，用于通过烯胺形成亲核活化醛，以及氢键供体，用于烯酸酯的亲电活化。正确选择氢键供体对于化学选择性至关重要，这需要最大限度地减少来自高醛醇反应的竞争。从环庚烯六步合成 (−)-yohimbane 证明了效用。
• Transannular Diels-Alder reaction studies with an activated dienophile. An enantioselective synthesis of an A.B.C.[6.6.6] trans-syn-cis tricycle
  作者：Louis Barriault、Stéphane G. Ouellet、Pierre Deslongchamps

  DOI：10.1016/s0040-4020(97)00997-6

  日期：1997.11

  The synthesis and transannular Diels-Alder reaction of a chiral 14 membered trans-cis-cis (TCC) macrocyclic triene with an activated dienophile leading to an A.B.C.[6.6.6.] tricyclic compound are described. The outcome of the TADA reaction under thermal and catalyzed conditions is discussed. (C) 1997 Elsevier Science Ltd.
• Asymmetric aza-Michael addition: synthesis of (−)-allosedridine and (−)-2-epi-ethylnorlobelol
  作者：Li-Ju Chen、Duen-Ren Hou

  DOI：10.1016/j.tetasy.2008.02.019

  日期：2008.4

  The combination of cross-metathesis and aza-Michael addition is an efficient method for generating piperidine alkaloids. Allosedridine and 2-epi-ethylnorlobelol were synthesized in six steps with ca. 25% overall yield. The aza-Michael addition is reversible for phenyl and alkyl ketones; however, the epimerization is not observed for the corresponding ester and amide. (c) 2008 Elsevier Ltd. All rights reserved.