(2S)-3-methyl-2-((1S)-1-phenylbut-3-enylamino)butan-1-ol | 154228-41-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S)-3-methyl-2-((1S)-1-phenylbut-3-enylamino)butan-1-ol
• 英文别名: N-[1(S)-phenyl-3-buten-1-yl]-(S)-valinol；1-Butanol, 3-methyl-2-[[(1S)-1-phenyl-3-butenyl]amino]-, (2S)-；(2S)-3-methyl-2-[[(1S)-1-phenylbut-3-enyl]amino]butan-1-ol
• CAS: 154228-41-8
• 化学式: C₁₅H₂₃NO
• 分子量: 233.354
• InChiKey: LDXIGNXDPWTJFQ-LSDHHAIUSA-N

物化性质

• 沸点：
  350.5±30.0 °C(Predicted)
• 密度：
  0.969±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-3-methyl-2-((1S)-1-phenylbut-3-enylamino)butan-1-ol 在 过碘酸 作用下， 以 吡啶 为溶剂， 反应 2.0h， 生成 N-((S)-1-phenylbut-3-enyl)acetamide
  参考文献：
  名称：

  Aluminum-Controlled Reactivity and Diastereoselectivity toward Radical Reactions of Optically Active Aldimines with Metallic Samarium

  摘要：

  The intermolecular pinacol-type coupling reaction and allylation reaction of optically active imines bearing a beta -hydroxy group were performed stereoselectively with metallic samarium after treatment of the imines with trimethylaluminum.

  DOI：

  10.1021/jo0014616
• 作为产物：
  描述：

  L-缬氨酸甲酯盐酸盐 在 copper(l) iodide 、 lithium aluminium tetrahydride 、 magnesium sulfate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 7.25h， 生成 (2S)-3-methyl-2-((1S)-1-phenylbut-3-enylamino)butan-1-ol
  参考文献：
  名称：

  Enantioselective Synthesis of Homoallylic Amines by Addition of Allylmetal Reagents to Imines Derived from (S)-Valine Esters

  摘要：

  Grignard and Barbier procedures have been applied to the addition of allylmetal (Zn, Cu, Pb, Bi, Al, In) species to imines derived from (S)-valine esters, principally the methyl ester. The Zn-mediated, CeCl3- or SnCl2-catalyzed ''Barbier'' reactions of the imines with allyl bromide in THF in Ar atmosphere at room temperature proved particularly convenient, efficient and selective, providing the secondary homoallylic amines with excellent to perfect diastereoselectivity. The si face of the imine was attacked preferentially in every case. The addition of allylzinc bromide to aromatic imines was affected by reversibility, which caused the lowering of the diastereoisomeric ratio with increasing the reaction time. However, the retroallylation reaction could be avoided by performing the reaction in the presence of trace amounts of water, or by using CeCl3.7H(2)O as the catalyst, although at the expense of the reaction rate. The bimetal redox systems Al-PbBr2, -SnCl2, -TiCl4, and -BiCl3 were applied to the allylation of the imines derived from methyl valinate, but satisfactory results were achieved only with Al-BiCl3 and -TiCl4 systems. However, the use of the Al(Hg) and Al-PbBr2 system afforded almost perfect chemo- and diastereoselectivity on the benzaldehyde imine derived from tert-butyl (S)-valinate. The synthesis of (S)-1-phenyl-3-butenamine from the corresponding secondary homoallylic amine was accomplished by a two-step sequence, consisting of the controlled reduction of the methyl ester with LiAlH4 and subsequent oxidative cleavage with H5IO6-MeNH(2).

  DOI：

  10.1021/jo00104a037

文献信息

• Enantioselective synthesis of homoallylic amines. Evidence of reversible addition of allylzinc bromide to aromatic imines derived from (S)-valine methyl ester and (S)-valinol
  作者：Allaye Bocoum、Diego Savoia、Achille Umani-Ronchi

  DOI：10.1039/c39930001542

  日期：——

  The reaction of aromatic and aliphatic imines derived from (S)-valine methyl ester and (S)-valinol with allyl bromide and zinc in tetrahydrofuran affords homoallylic amines with up to 100% diastereoisomeric excess (d.e.), but in the case of the aromatic imines the diastereoselectivity is lowered by increasing the reaction time, owing to the reversibility of the allylation reaction.

  由(S)-缬氨酸甲酯和(S)-缬氨醇衍生的芳香族和脂肪族亚胺与椰基溴和锌在四氢呋喃中反应，生成具有高达100%差异异构体过量（d.e.）的同烯丙胺，但在芳香族亚胺的情况下，随着反应时间的增加，差异选择性降低，这是由于烯丙基化反应的可逆性所致。
• Diastereoselective allylation and alkylation of optically active imines with metallic samarium and a catalytic amount of iodine
  作者：Reiko Yanada、Nobuyuki Negoro、Masanori Okaniwa、Toshiro Ibuka

  DOI：10.1016/s0040-4020(99)00854-6

  日期：1999.12

  Barbier-type allylation and alkylation of optically active imines such as N-benzylidenevalinol methyl ether was performed with metallic samarium, a catalytic amount of iodine, and allyl or alkyl halides. This reaction proceeded in a highly diastereoselective manner in THF at room temperature.

  用金属sa，催化量的碘和烯丙基或烷基卤化物进行光学活性的亚胺如N-苄叉亚戊醇甲基醚的Barbier型烯丙基化和烷基化。该反应在室温下以高度非对映选择性的方式进行。
• Diastereoselective Allylation of Optically Active Imines with Metallic Samarium
  作者：Nobuyuki Negoro、Reiko Yanada、Masanori Okaniwa、Kazuo Yanada、Tetsuro Fujita

  DOI：10.1055/s-1998-1818

  日期：1998.8

  Barbier-type allylation of optically active imines such as N-benzylidenevalinol methyl ether was performed with metallic samarium, a catalytic amout of iodine, and allyl bromide. This reaction proceeded in a highly diastereoselective manner in THF at room temperature.

  对光学活性亚胺（如 N-benzylidenevalinol 甲基醚）进行Barbier类型的烯丙基化反应，使用金属钐、催化量的碘和烯丙基溴。该反应在常温下的THF中以高度的非对映选择性进行。
• Diastereoselective Barbier-Type and Palladium-Mediated Allylation of Optically Active Aldimine with Allylindium Reagents
  作者：Reiko Yanada、Akira Kaieda、Yoshiji Takemoto

  DOI：10.1021/jo015719j

  日期：2001.11.1
• Asymmetric Synthesis of δ-Substituted α,β-Unsaturated δ-Lactams by Ring Closing Metathesis of Enantiomerically Pure <i>N</i>-Acryloyl-homoallylic Amines
  作者：Claudio Fiorelli、Diego Savoia

  DOI：10.1021/jo0703000

  日期：2007.8.1

  Optically pure secondary homoallylic amines, obtained by highly diastereoselective addition of allylmetal reagents to imines derived from chiral amines, were N-dealkylated, and the primary amines were converted to N-acryloyl amides. Then, ring closing metathesis gave delta-substituted delta-lactams in good overall yields.