(S)-(2l,6l)-6-methyl-3-(1-methylethyl)-2-(phenylmethyl)-1,3,2-oxazaphosphorinane 2-sulfide | 172878-06-7

• 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: (S)-(2l,6l)-6-methyl-3-(1-methylethyl)-2-(phenylmethyl)-1,3,2-oxazaphosphorinane 2-sulfide
• 英文别名: (2S,6S)-2-benzyl-6-methyl-3-propan-2-yl-2-sulfanylidene-1,3,2lambda5-oxazaphosphinane；(2S,6S)-2-benzyl-6-methyl-3-propan-2-yl-2-sulfanylidene-1,3,2λ5-oxazaphosphinane
• CAS: 172878-06-7
• 化学式: C₁₄H₂₂NOPS
• 分子量: 283.375
• InChiKey: KUOZVDIPRNIEBQ-GUYCJALGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  44.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(2l,6l)-6-methyl-3-(1-methylethyl)-2-(phenylmethyl)-1,3,2-oxazaphosphorinane 2-sulfide 在 盐酸 、 叔丁基锂 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 15.34h， 生成 (R)-(1-苯基乙基)膦酸
  参考文献：
  名称：

  Alkylations of Chiral, Phosphoryl- and Thiophosphoryl-Stabilized Carbanions

  摘要：

  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.

  DOI：

  10.1021/ja00153a009
• 作为产物：
  描述：

  benzylphosphonic dichloride 在 劳森试剂 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 (S)-(2l,6l)-6-methyl-3-(1-methylethyl)-2-(phenylmethyl)-1,3,2-oxazaphosphorinane 2-sulfide
  参考文献：
  名称：

  Alkylations of Chiral, Phosphoryl- and Thiophosphoryl-Stabilized Carbanions

  摘要：

  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.

  DOI：

  10.1021/ja00153a009