α-diethylphosphonooxy-α-ethoxycarbonylphenylacetonitrile

• 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: α-diethylphosphonooxy-α-ethoxycarbonylphenylacetonitrile
• 英文别名: (ethoxycarbonyl)(cyano)(phenyl)methyl diethyl phosphate；Ethyl 2-cyano-2-diethoxyphosphoryloxy-2-phenylacetate
• 化学式: C₁₅H₂₀NO₆P
• 分子量: 341.301
• InChiKey: LNFWHICOWKGISW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  94.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-(Diethylphosphonooxy)-2-phenylethanenitrile 、 氯甲酸乙酯 在 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以59%的产率得到α-diethylphosphonooxy-α-ethoxycarbonylphenylacetonitrile
  参考文献：
  名称：

  Kurihara, Takushi; Santo, Kazunori; Harusawa, Shinya, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 12, p. 4777 - 4788

  摘要：

  DOI：

文献信息

• Cyanide Ion Promoted Addition of Acyl Phosphonates to Ethyl Cyanoformate:  Synthesis of Tertiary Carbinols via Tandem Carbon−Carbon Bond Formations
  作者：Ayhan S. Demir、Barbaros Reis、Ömer Reis、Serkan Eymür、Mehmet Göllü、Servet Tural、Gülüzar Saglam

  DOI：10.1021/jo0710073

  日期：2007.9.1

  [GRAPHICS]New cyanation/phosphonate -phosphate rearrangement/Cacylation reactions of cyartophosphate anion with cyanoformate esters are described. Phase-transfer cocatalysts facilitate cyanide-catalyzed reactions between acyl phosphonates and cyanoformates to afford protected tertiary carbinol products in good to excellent yields (74-95%). Ethyl cyanoformate is used as a cyanide source and electrophile. The scope of the reaction was investigated by using a number of benzoyl and acyl phosphonates along with ethyl cyanoformate. Representative chemoselective reduction of the product 5a afforded ethyl 3-amino-2- iydroxy-2-phenylpropanoate (13) in good yield.
• KURIHARA, TAKUSHI;SANTO, KAZUNORI;HARUSAWA, SHINYA;YONEDA, RYUJI, CHEM. AND PHARM. BULL., 35,(1987) N 12, 4777-4788
  作者：KURIHARA, TAKUSHI、SANTO, KAZUNORI、HARUSAWA, SHINYA、YONEDA, RYUJI

  DOI：——

  日期：——
• Kurihara, Takushi; Santo, Kazunori; Harusawa, Shinya, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 12, p. 4777 - 4788
  作者：Kurihara, Takushi、Santo, Kazunori、Harusawa, Shinya、Yoneda, Ryuji

  DOI：——

  日期：——