1,1-Diethoxy-2-hydroxy-2-phenylethyl-1-(diphenylphosphine oxide) | 188546-71-6

• 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: 1,1-Diethoxy-2-hydroxy-2-phenylethyl-1-(diphenylphosphine oxide)
• 英文别名: 2-Diphenylphosphoryl-2,2-diethoxy-1-phenylethanol
• CAS: 188546-71-6
• 化学式: C₂₄H₂₇O₄P
• 分子量: 410.45
• InChiKey: SKHDHBYYWFXTIO-UHFFFAOYSA-N

物化性质

• 沸点：
  541.3±50.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-Diethoxy-2-hydroxy-2-phenylethyl-1-(diphenylphosphine oxide) 在 甲基磺酰胺 、 potassium tert-butylate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 0.25h， 生成 D-(-)-扁桃酸乙酯
  参考文献：
  名称：

  A New Asymmetric Formylation of Aldehydes

  摘要：

  DOI：

  10.1002/anie.199702531
• 作为产物：
  描述：

  二苯基氯化膦 、 alkaline earth salt of/the/ methylsulfuric acid 在 (6-氨基己基氨基)甲基-(二乙氧基甲基)硅 作用下， 以 四氢呋喃 为溶剂， 反应 3.25h， 生成 1,1-Diethoxy-2-hydroxy-2-phenylethyl-1-(diphenylphosphine oxide)
  参考文献：
  名称：

  Asymmetric Nucleophilic Acylation of Aldehydes via 1,1-Heterodisubstituted Alkenes

  摘要：

  Aldehydes are asymmetrically acylated by a two step sequence that is initiated by a homologation step to 1,1-heterodisubstituted alkenes followed by asymmetric dihydroxylation. Thus, ketene O,S-acetals are efficiently prepared from aldehydes by a Peterson olefination with lithiated methoxy-phenylthiotrimethylsilyl methane 14 as the C-1 source. Although they are dihydroxylated with the Sharpless catalyst with moderate to good enantioselectivity (62-80% ee), the process is not efficient owing to the low chemical yields of the desired alpha-hydroxy methyl esters (7-37%). Use of the corresponding sulfoxide 24 or sulfon 25 led to an improved chemical yield of alpha-hydroxy methyl ester 19, but the stereoselectivity was diminished. In contrast, intermediate ketene O,O-acetals are prepared by a Horner-Wittig reaction with phosphine oxide 31 and are dihydroxylated both with good chemical and stereochemical yield. The concept is applicable to aromatic, aliphatic, and chiral aldehydes. For example, this short sequence allows exclusive and independent preparation of both diastereomeric heptoses 69a and 69b.

  DOI：

  10.1002/(sici)1521-3765(19990802)5:8<2270::aid-chem2270>3.0.co;2-l

文献信息

• A Horner-Wittig solution to the synthesis of ketene, O,O-acetals.
  作者：T.A.M. van Schaik、A.V. Henzen、A. van der Gen

  DOI：10.1016/s0040-4039(00)81641-x

  日期：1983.1

  Aldehydes as well as ketones can be converted into their homologous ketene, O-O-acetals by a Horner-Wittig reaction with dialkoxymethyl diphenylphosphine oxides.

  醛和酮可以通过与二烷氧基甲基二苯基膦氧化物的霍纳-威蒂希反应转化为它们的同源烯酮OO-乙缩醛。
• Lithiated Dimethoxymethyl Diphenyl Phosphine Oxide, A Versatile Formiate Carbanion Equivalent
  作者：Holger Monenschein、Marco Brünjes、Andreas Kirschning

  DOI：10.1055/s-2002-20486

  日期：——

  Aldehydes are homologated to the corresponding α-hydroxy methyl esters using lithiated dimethoxymethyl diphenyl phosphine oxide. The primary addition product of this Horner-Wittig process collapses to the corresponding α-hydroxy ester under proton-catalyzed conditions.

  使用锂化的二甲氧基甲基二苯基膦氧化物将醛类同系为相应的 α-羟基甲酯。在质子催化条件下，该 Horner-Wittig 过程的主要加成产物分解为相应的 α-羟基酯。
• A New Asymmetric Formylation of Aldehydes
  作者：Andreas Kirschning、Gerald Dräger、Alexander Jung

  DOI：10.1002/anie.199702531

  日期：1997.2.14
• SCHAIK, T. A. M.;HENZEN, A. V.;GEN, A., TETRAHEDRON LETT., 1983, 24, N 12, 1303-1306
  作者：SCHAIK, T. A. M.、HENZEN, A. V.、GEN, A.

  DOI：——

  日期：——
• Asymmetric Nucleophilic Acylation of Aldehydes via 1,1-Heterodisubstituted Alkenes
  作者：Holger Monenschein、Gerald Dräger、Alexander Jung、Andreas Kirschning

  DOI：10.1002/(sici)1521-3765(19990802)5:8<2270::aid-chem2270>3.0.co;2-l

  日期：1999.8.2

  Aldehydes are asymmetrically acylated by a two step sequence that is initiated by a homologation step to 1,1-heterodisubstituted alkenes followed by asymmetric dihydroxylation. Thus, ketene O,S-acetals are efficiently prepared from aldehydes by a Peterson olefination with lithiated methoxy-phenylthiotrimethylsilyl methane 14 as the C-1 source. Although they are dihydroxylated with the Sharpless catalyst with moderate to good enantioselectivity (62-80% ee), the process is not efficient owing to the low chemical yields of the desired alpha-hydroxy methyl esters (7-37%). Use of the corresponding sulfoxide 24 or sulfon 25 led to an improved chemical yield of alpha-hydroxy methyl ester 19, but the stereoselectivity was diminished. In contrast, intermediate ketene O,O-acetals are prepared by a Horner-Wittig reaction with phosphine oxide 31 and are dihydroxylated both with good chemical and stereochemical yield. The concept is applicable to aromatic, aliphatic, and chiral aldehydes. For example, this short sequence allows exclusive and independent preparation of both diastereomeric heptoses 69a and 69b.