[2S,2(1S,3E)]-2-phenyl-2-[[1-phenyl-4-(trimethylsilanyl)but-3-enyl]amino]ethanol | 288145-04-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: [2S,2(1S,3E)]-2-phenyl-2-[[1-phenyl-4-(trimethylsilanyl)but-3-enyl]amino]ethanol
• 英文别名: (2S)-2-phenyl-2-[[(E,1S)-1-phenyl-4-trimethylsilylbut-3-enyl]amino]ethanol
• CAS: 288145-04-0
• 化学式: C₂₁H₂₉NOSi
• 分子量: 339.553
• InChiKey: ISPDQPNDSPGXCR-TUFRZFPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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,2(1S,3E)]-2-phenyl-2-[[1-phenyl-4-(trimethylsilanyl)but-3-enyl]amino]ethanol 在 lead(IV) acetate 、 苯肼 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 生成 (E)-(S)-1-Phenyl-4-trimethylsilanyl-but-3-enylamine
  参考文献：
  名称：

  Short asymmetric syntheses of homoallylic, homopropargylic and allenic silylated primary amines

  摘要：

  Amino alcohols derived from phenylglycinol and having vinyl-, alkynyl- or allenylsilane moieties were transformed in the corresponding primary amines in two steps: oxidative cleavage of phenylglycinol and transimination with phenylhydrazine. This methodology gave general access to enantiomerically enriched amines without loss of enantioselectivity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.066
• 作为产物：
  描述：

  L-苯甘氨醇 在 四甲基乙二胺 、 仲丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 生成 [2S,2(1S,3E)]-2-phenyl-2-[[1-phenyl-4-(trimethylsilanyl)but-3-enyl]amino]ethanol
  参考文献：
  名称：

  在钛盐的存在下，将甲硅烷基化的有机锂试剂与恶唑烷加成，区域选择性发生剧烈变化

  摘要：

  恶唑烷与有机锂试剂之间的非对映选择性反应得到具有手性乙烯基和炔基硅烷部分的β-氨基醇。当在异丙醇钛存在下进行这些反应时，从α-位置到γ-位置的区域选择性发生了有意义的变化，因为由此产生了烯丙基和烯丙基硅烷衍生物。

  DOI：

  10.1016/s0040-4039(00)00947-3

文献信息

• Dramatic change of regioselectivity in the addition of silylated organolithium reagents with oxazolidines induced by the presence of a titanium salt
  作者：Claude Agami、Sébastien Comesse、Catherine Kadouri-Puchot

  DOI：10.1016/s0040-4039(00)00947-3

  日期：2000.8

  Diastereoselective reactions between oxazolidines and organolithium reagents afford β-amino alcohols having chiral vinyl and alkynylsilane moieties. A meaningful change of regioselectivity, from the α- to the γ-position, occurred when these reactions were performed in the presence of titanium isopropoxide, since allyl and allenylsilane derivatives were thus produced.

  恶唑烷与有机锂试剂之间的非对映选择性反应得到具有手性乙烯基和炔基硅烷部分的β-氨基醇。当在异丙醇钛存在下进行这些反应时，从α-位置到γ-位置的区域选择性发生了有意义的变化，因为由此产生了烯丙基和烯丙基硅烷衍生物。
• The Intriguing Reactivity of Functionalized β-Amino Alcohols with Glyoxal:  Application to a New Expedient Enantioselective Synthesis of <i>trans</i>-6-Alkylpipecolic Acids
  作者：Claude Agami、Sébastien Comesse、Catherine Kadouri-Puchot

  DOI：10.1021/jo010780+

  日期：2002.4.1

  New beta-amino alcohols possessing a vinylsilane moiety were reacted with glyoxal to produce lactones that were transformed in three steps in enantiopure pipecolic acid derivatives. The key step was a totally diastereoselective ene-iminium cyclization, whose mechanism can be viewed as a direct cyclization of the vinylsilane moiety onto the iminium ion. The reactivity of two beta-amino alcohols having

  使具有乙烯基硅烷部分的新的β-氨基醇与乙二醛反应生成内酯，将内酯分三步转化为对映体纯的胡椒酸衍生物。关键步骤是完全非对映选择性的烯-亚胺环化，其机理可以看作是乙烯基硅烷部分直接环化到亚胺离子上。还检查了具有烯丙基硅烷终止剂的两种β-氨基醇的反应性。它们对乙二醛的反应性差异可归因于碳正离子的干预，碳正离子的行为随三甲基甲硅烷基的位置而异。
• Asymmetric Syntheses of New Functionalized <i>β</i>-Amino Alcohols via Diastereoselective Addition of Organometallic Reagents onto Oxazolidines
  作者：Claude Agami、Sébastien Comesse、Catherine Kadouri-Puchot

  DOI：10.1021/jo010779a

  日期：2002.3.1

  Diastereoselective reactions between (S)-phenylglycinol-derived oxazolidines and two unsaturated organolithium reagents afforded chiral beta-amino alcohols having vinyl and alkynylsilane moieties. When the same reactions were performed in the presence of titanium isopropoxide, a dramatic change of regioselectivity was observed, from the alpha- to the gamma-position, thus producing beta-amino alcohols

  （S）-苯基甘醇衍生的恶唑烷与两种不饱和有机锂试剂之间的非对映选择性反应提供了具有乙烯基和炔基硅烷部分的手性β-氨基醇。当在异丙醇钛存在下进行相同的反应时，观察到区域选择性从α-到γ-位置的剧烈变化，从而产生具有烯丙基或烯丙基硅烷官能团的β-氨基醇。建议对每种情况合理化观察到的非对映选择性。
• Short asymmetric syntheses of homoallylic, homopropargylic and allenic silylated primary amines
  作者：Sébastien Comesse、Benjamin Bertin、Catherine Kadouri-Puchot

  DOI：10.1016/j.tetlet.2004.03.066

  日期：2004.5

  Amino alcohols derived from phenylglycinol and having vinyl-, alkynyl- or allenylsilane moieties were transformed in the corresponding primary amines in two steps: oxidative cleavage of phenylglycinol and transimination with phenylhydrazine. This methodology gave general access to enantiomerically enriched amines without loss of enantioselectivity. (C) 2004 Elsevier Ltd. All rights reserved.