(S)-2-(1,3-Dihydro-isoindol-2-yl)-3-phenyl-propionaldehyde | 111061-20-2

• 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: (S)-2-(1,3-Dihydro-isoindol-2-yl)-3-phenyl-propionaldehyde
• 英文别名: (2S)-2-(1,3-dihydroisoindol-2-yl)-3-phenylpropanal
• CAS: 111061-20-2
• 化学式: C₁₇H₁₇NO
• 分子量: 251.328
• InChiKey: DETRBJPOGJSOEI-KRWDZBQOSA-N

物化性质

• 沸点：
  356.0±30.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-(1,3-Dihydro-isoindol-2-yl)-3-phenyl-propionaldehyde 、 lithium dimethylcuprate 生成 (2S,3S)-3-(1,3-Dihydro-isoindol-2-yl)-4-phenyl-butan-2-ol
  参考文献：
  名称：

  REETZ, MANFRED T.;DREWES, MARK W.;SCHMITZ, ALFRED, ANGEW. CHEM., 99,(1987) N 11, 1186-1188

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-2-(1,3-Dihydro-isoindol-2-yl)-3-phenyl-propan-1-ol 在 草酰氯 作用下， 以 二甲基亚砜 为溶剂， 生成 (S)-2-(1,3-Dihydro-isoindol-2-yl)-3-phenyl-propionaldehyde
  参考文献：
  名称：

  Diastereoselection during 1,2-Addition of the Allylindium Reagent to α-Thia and α-Amino Aldehydes in Aqueous and Organic Solvents

  摘要：

  The stereochemistry of the indium-promoted reaction of allyl bromide with alpha-thia (PhS and MeS), disubstituted alpha-amino (Bn2N, Me2N, isoindolyl), and protected alpha-amino aldehydes (Ac and Boc) in water has been evaluated. The reactions involving the sulfur derivatives are minimally diastereoselective, indicating that the allylindium reagent is not thiophilic. Chelation is not observed and pi-facial discrimination is achieved via Felkin-Ahn transition states under the steric control of the substituents. The Garner aldehyde is also anti-diastereoselective. Interestingly, N-acetylmannosamine is appreciably responsive to chelation control and is capable of generating 90% of the syn beta-amino alcohol when reacted in a 0.5 M NH4Cl solution. While the alpha-dibenzylamino substituent is too bulky to enter into complexation, the alpha-dimethylamino group is not and can lead to high levels (99%) of syn diastereomer. The size of other neighboring substituents does have an impact on pi-facial discrimination in these systems and can erode the stereoselectivity accordingly.

  DOI：

  10.1021/jo970274d

文献信息

• Reetz, Manfred T.; Drewes, Mark W.; Schmitz, Alfred, Angewandte Chemie, 1987, vol. 99, # 11, p. 1186 - 1188
  作者：Reetz, Manfred T.、Drewes, Mark W.、Schmitz, Alfred

  DOI：——

  日期：——