1,1-Dideuterio-3-(phenylselenenyl)propanol | 124006-31-1

• 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-Dideuterio-3-(phenylselenenyl)propanol
• 英文别名: 1,1-dideuterio-3-phenylselanylpropan-1-ol
• CAS: 124006-31-1
• 化学式: C₉H₁₂OSe
• 分子量: 217.138
• InChiKey: HMZBGYHWZQCHDA-RJSZUWSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.82
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1,1-Dideuterio-3-(phenylselenenyl)propanol 、 (S)-N-(tert-Butoxycarbonyl)proline ethyl carbonate 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以90%的产率得到(S)-N-(tert-Butoxycarbonyl)proline 1,2-dideuterio-3-(phenylselenenyl)propyl ester
  参考文献：
  名称：

  Asymmetric induction reactions. V. The palladium-catalyzed asymmetric .alpha.-allylation of carbonyl compounds with chiral allyl esters via enamines and imines

  摘要：

  A novel and excellent method for asymmetric alpha-allylation of carbonyl compounds via their chiral enamines or imines bearing allyl eaters has been developed. Readily available chiral allyl eaters having chirality at the alpha-position of the eater carbonyl group, such as (S)-proline and other (S)-alpha-amino acid allyl esters, have been found to serve as good asymmetric allylating reagents in palladium-catalyzed reactions of the chiral enamines and imines derived from them. The use of (S)-proline or (S)-valine allyl esters as the amino parts in the enamines or imines provided the highest optical yields of the corresponding alpha-allyl carbonyl compounds. A mechanism for asymmetric induction is proposed based on the stereochemical results obtained.

  DOI：

  10.1021/jo00080a033
• 作为产物：
  描述：

  二苯基二硒醚 在 sodium tetrahydroborate 、 lithium aluminium deuteride 作用下， 以 乙醚 为溶剂， 反应 19.33h， 生成 1,1-Dideuterio-3-(phenylselenenyl)propanol
  参考文献：
  名称：

  Asymmetric induction reactions. V. The palladium-catalyzed asymmetric .alpha.-allylation of carbonyl compounds with chiral allyl esters via enamines and imines

  摘要：

  A novel and excellent method for asymmetric alpha-allylation of carbonyl compounds via their chiral enamines or imines bearing allyl eaters has been developed. Readily available chiral allyl eaters having chirality at the alpha-position of the eater carbonyl group, such as (S)-proline and other (S)-alpha-amino acid allyl esters, have been found to serve as good asymmetric allylating reagents in palladium-catalyzed reactions of the chiral enamines and imines derived from them. The use of (S)-proline or (S)-valine allyl esters as the amino parts in the enamines or imines provided the highest optical yields of the corresponding alpha-allyl carbonyl compounds. A mechanism for asymmetric induction is proposed based on the stereochemical results obtained.

  DOI：

  10.1021/jo00080a033

文献信息

• Palladium-catalyzed asymmetric allylations of aldehydes via (S)-proline allyl ester enamines
  作者：Kunio Hiroi、Jun Abe、Kyoko Suya、Shuko Sato

  DOI：10.1016/s0040-4039(00)99514-5

  日期：1989.1

  Treatment of chiral enamine , derived from (S)-proline allyl ester () and 2-phenylpropionaldehyde (), with tetrakis(triphenylphosphine)-palladium provided (R)-(-)-2-methyl-2-phenyl-4-pentenylaldehyde () with high enantiomeric excess. The mechanism for this asymmetric induction is discussed.

  用四（三苯基膦）-钯提供的（R）-（-）-2-甲基-2-苯基-4-戊烯基醛处理衍生自（S）-脯氨酸烯丙基酯（）和2-苯基丙醛（）的手性烯胺（）具有较高的对映体过量。讨论了这种不对称感应的机制。
• HIROI, KUNIO;ABE, JUN;SUYA, KYOKO;SATO, SHUKO, TETRAHEDRON LETT., 30,(1989) N2, C. 1543-1546
  作者：HIROI, KUNIO、ABE, JUN、SUYA, KYOKO、SATO, SHUKO

  DOI：——

  日期：——