(2R,6S)-2-benzyl-3-tert-butyl-6-methyl-1,3,2lambda5-oxazaphosphinane 2-oxide | 130613-89-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧氮杂膦
• 英文名称: (2R,6S)-2-benzyl-3-tert-butyl-6-methyl-1,3,2lambda5-oxazaphosphinane 2-oxide
• 英文别名: (2R,6S)-2-benzyl-3-tert-butyl-6-methyl-1,3,2λ5-oxazaphosphinane 2-oxide
• CAS: 130613-89-7
• 化学式: C₁₅H₂₄NO₂P
• 分子量: 281.335
• InChiKey: DMOCJTCEWCPTRA-ORAYPTAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  (2R,6S)-2-benzyl-3-tert-butyl-6-methyl-1,3,2lambda5-oxazaphosphinane 2-oxide 在 叔丁基锂 、 溶剂黄146 作用下， 生成 (2R,6S)-3-tert-butyl-6-methyl-2-[(1S)-1-phenylethyl]-1,3,2λ5-oxazaphosphinane 2-oxide
  参考文献：
  名称：

  Stereoselective alkylations of chiral, phosphorus-stabilized benzylic carbanions

  摘要：

  DOI：

  10.1021/jo00311a003
• 作为产物：
  描述：

  benzylphosphonic dichloride 、 (S)-4-N-tert-butylamino-2-butanol 在 三乙胺 作用下， 以49%的产率得到(2R,6S)-2-benzyl-3-tert-butyl-6-methyl-1,3,2lambda5-oxazaphosphinane 2-oxide
  参考文献：
  名称：

  Stereoselective alkylations of chiral, phosphorus-stabilized benzylic carbanions

  摘要：

  DOI：

  10.1021/jo00311a003

文献信息

• Asymmetric electrophilic amination of chiral phosphorus-stabilized anions
  作者：Scott E. Denmark、Naoto Chatani、Sunil V. Pansare

  DOI：10.1016/s0040-4020(01)88883-9

  日期：1992.1

  The asymmetric electrophilic amination of phosphorus-stabilized anions derived from chiral oxazaphosphorinanes and diazaphospholidines is described. Trisyl azide is the reagent of choice for the amination process. The reaction is shown to be dependent on auxiliary structure, nature of the P-alkyl substituent and choice of amination procedure. Using the oxazaphosphorinanes 1a and cis-1e a high level

  描述了衍生自手性氧杂氮磷腈和二氮磷吡啶的磷稳定阴离子的不对称亲电胺化反应。三叠氮化物是胺化过程的首选试剂。已表明该反应取决于辅助结构，对-烷基取代基的性质和胺化方法的选择。使用草氮磷膦酸酯1a和cis-1e可以实现高水平的不对称诱导。在（S）对映体中，Scalemic cis-1e提供具有92％ee的α-氨基膦酸13。讨论了构象和辅助结构对立体选择性的影响。
• Alkylations of Chiral, Phosphoryl- and Thiophosphoryl-Stabilized Carbanions
  作者：Scott E. Denmark、Chien-Tien Chen

  DOI：10.1021/ja00153a009

  日期：1995.12

  A general method for the preparation of enantiomerically enriched phosphonic acids and phosphonates with three different a-substitution patterns (aryl, alkyl, and alkoxy) has been developed. Anions derived from enantiomerically enriched thiophosphonamidates (2-thioxo-1,3,2-oxazaphosphorinanes) underwent smooth electrophilic substitutions with excellent diastereoselectivity for both cis and trans stereoisomers. Highly enantioselective synthesis of alpha-alkoxyphosphonates in either antipodal form can be achieved by the employment of highly diastereoselective alkylation with anions derived from the corresponding P-methoxymethyl analogs in the presence of HMPA or PMDTA. Implications for the aggregation states and reactive conformations of the anions are discussed.
• DENMARK, SCOTT E.;DOROW, ROBERTA L., J. ORG. CHEM., 55,(1990) N4, C. 5926-5928
  作者：DENMARK, SCOTT E.、DOROW, ROBERTA L.

  DOI：——

  日期：——
• Stereoselective alkylations of chiral, phosphorus-stabilized benzylic carbanions
  作者：Scott E. Denmark、Roberta L. Dorow

  DOI：10.1021/jo00311a003

  日期：1990.11