Benzyl-carbamic acid (2S,3R)-3-[(1S,2R)-1-(diphenyl-phosphinoyl)-2-methyl-butyl]-oxiranylmethyl ester | 148554-71-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzyl-carbamic acid (2S,3R)-3-[(1S,2R)-1-(diphenyl-phosphinoyl)-2-methyl-butyl]-oxiranylmethyl ester
• 英文别名: [(2S,3R)-3-[(1S,2R)-1-diphenylphosphoryl-2-methylbutyl]oxiran-2-yl]methyl N-benzylcarbamate
• CAS: 148554-71-6
• 化学式: C₂₈H₃₂NO₄P
• 分子量: 477.54
• InChiKey: HGYSASCNFUYKSU-DXXVALNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Benzyl-carbamic acid (2S,3R)-3-[(1S,2R)-1-(diphenyl-phosphinoyl)-2-methyl-butyl]-oxiranylmethyl ester 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 以80%的产率得到(5S,3'R)-(Z)-3-Benzyl-4-(3'-methylpent-1'-enyl)oxazolidin-2-one
  参考文献：
  名称：

  Alkenyl oxazolidinones by stereoselective epoxidation of δ-hydroxy allylic phosphine oxides: Synthesis of any isomer (RR, RS, SR or SS; E or Z) bearing 1,4-related chiral centres across a double bond

  摘要：

  Alkenyl oxazolidinones 5 have been made from the urethane derivatives 4 of diphenylphosphinoyl epoxy alcohols 1 by a tandem intramolecular ring closure - Horner-Wittig elimination sequence. The stereoisomers of diphenylphosphinoyl epoxy alcohols containing further chiral centres have been made by enantio- and diastereoselective epoxidation, and converted stereospecifically to alkenyl oxazolidinones with 1,4-related chiral centres across a controlled geometry double bond.

  DOI：

  10.1016/s0040-4039(00)60383-0
• 作为产物：
  描述：

  (2-methylbutyl)diphenylphosphine oxide 在 双(乙腈)氯化钯(II) titanium(IV) isopropylate 、 叔丁基过氧化氢 、 sodium hydroxide 、 正丁基锂 、 L-(+)-酒石酸二异丙酯 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 120.0h， 生成 Benzyl-carbamic acid (2S,3R)-3-[(1S,2R)-1-(diphenyl-phosphinoyl)-2-methyl-butyl]-oxiranylmethyl ester
  参考文献：
  名称：

  Alkenyl oxazolidinones by stereoselective epoxidation of δ-hydroxy allylic phosphine oxides: Synthesis of any isomer (RR, RS, SR or SS; E or Z) bearing 1,4-related chiral centres across a double bond

  摘要：

  Alkenyl oxazolidinones 5 have been made from the urethane derivatives 4 of diphenylphosphinoyl epoxy alcohols 1 by a tandem intramolecular ring closure - Horner-Wittig elimination sequence. The stereoisomers of diphenylphosphinoyl epoxy alcohols containing further chiral centres have been made by enantio- and diastereoselective epoxidation, and converted stereospecifically to alkenyl oxazolidinones with 1,4-related chiral centres across a controlled geometry double bond.

  DOI：

  10.1016/s0040-4039(00)60383-0

文献信息

• Clayden, Jonathan; Warren, Stuart, Journal of the Chemical Society. Perkin transactions I, <hi>1998</hi>, # 17, p. 2923 - 2931
  作者：Clayden, Jonathan、Warren, Stuart

  DOI：——

  日期：——