(2S,3R)-2-(dibenzylamino)-1-phenylhex-5-en-3-ol | 111060-88-9

• 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: (2S,3R)-2-(dibenzylamino)-1-phenylhex-5-en-3-ol
• CAS: 111060-88-9
• 化学式: C₂₆H₂₉NO
• 分子量: 371.522
• InChiKey: PPOVYTPGAPWUMU-IZZNHLLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-(dibenzylamino)-1-phenylhex-5-en-3-ol 在 sodium tetrahydroborate 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 dimethyl sulfide borane 、 双氧水 作用下， 以 甲醇 为溶剂， 生成 (5S,1'S)-5-(1'-(dibenzylamino)-2'-phenylethyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Zinc-Mediated Allylation of N-Protected α-Amino Aldehydes in Aqueous Solution. Stereoselective Synthesis of Anti- and Syn-β-Amino Alcohols with Functionalized Allyl Groups

  摘要：

  在水中通过锌介导的2-(二苄基氨基)醛的烯丙基化反应，以高化学产率和良好的至优异的非对映选择性获得了具有不同取代烯丙基的抗-β-氨基醇。通过Swern氧化和NaBH4还原，以良好产率得到了高对映纯度的顺-β-氨基醇。

  DOI：

  10.1055/s-1997-804
• 作为产物：
  描述：

  N,N-二苄基-L-苯丙氨酸苄酯 在 indium 、 ammonium chloride 作用下， 反应 6.08h， 生成 (2S,3R)-2-(dibenzylamino)-1-phenylhex-5-en-3-ol
  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：——
• REETZ, MANFRED T., PURE AND APPL. CHEM., 60,(1988) N1, C. 1607-1614
  作者：REETZ, MANFRED T.

  DOI：——

  日期：——
• REETZ, MANFRED T.;DREWES, MARK W.;SCHMITZ, ALFRED, ANGEW. CHEM., 99,(1987) N 11, 1186-1188
  作者：REETZ, MANFRED T.、DREWES, MARK W.、SCHMITZ, ALFRED

  DOI：——

  日期：——
• Diastereoselection during 1,2-Addition of the Allylindium Reagent to α-Thia and α-Amino Aldehydes in Aqueous and Organic Solvents
  作者：Leo A. Paquette、Thomas M. Mitzel、Methvin B. Isaac、Curtis F. Crasto、William W. Schomer

  DOI：10.1021/jo970274d

  日期：1997.6.1

  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.
• Zinc-Mediated Allylation of <i>N</i>-Protected α-Amino Aldehydes in Aqueous Solution. Stereoselective Synthesis of <i>Anti</i>- and <i>Syn</i>-β-Amino Alcohols with Functionalized Allyl Groups
  作者：Stephen Hanessian、Haeil Park、Rui-Yang Yang

  DOI：10.1055/s-1997-804

  日期：1997.4

  Anti-β-amino alcohols with differently substituted allyl groups were obtained in high chemical yields and in good to excellent diastereoselectivities via Zn-mediated allylation of 2-(dibenzylamino)aldehydes in aqueous media. Swern oxidation, and reduction with NaBH4 gave enantiopure syn-β-amino alcohols in good yields.

  在水中通过锌介导的2-(二苄基氨基)醛的烯丙基化反应，以高化学产率和良好的至优异的非对映选择性获得了具有不同取代烯丙基的抗-β-氨基醇。通过Swern氧化和NaBH4还原，以良好产率得到了高对映纯度的顺-β-氨基醇。