(3S,1'R)-(+)-N-(1-phenylbutoxy)-1,3-diphenyl-3-prop-1-enylamine | 193091-78-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (3S,1'R)-(+)-N-(1-phenylbutoxy)-1,3-diphenyl-3-prop-1-enylamine
• 英文别名: (E,1S)-1,3-diphenyl-N-[(1R)-1-phenylbutoxy]prop-2-en-1-amine
• CAS: 193091-78-0
• 化学式: C₂₅H₂₇NO
• 分子量: 357.495
• InChiKey: PKESNQCSDIGWAH-QKTRXYFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,1'R)-(+)-N-(1-phenylbutoxy)-1,3-diphenyl-3-prop-1-enylamine 在 Grubbs catalyst first generation potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (S)-2-Phenyl-1-((R)-1-phenyl-butoxy)-2,5-dihydro-1H-pyrrole
  参考文献：
  名称：

  肟加成闭环复分解不对称合成2-取代的5-、6-和7-元氮杂环

  摘要：

  二烯 6 和 9 的闭环复分解反应分别产生氮杂环 7 和 10，其中一个 10c 被转化为 (R)-(-)-coniine。

  DOI：

  10.1039/b005353h
• 作为产物：
  描述：

  (R)-(+)-N-(1-phenylbutoxy)phthalimide 在 三氟化硼乙醚 、 一水合肼 作用下， 反应 2.75h， 生成 (3S,1'R)-(+)-N-(1-phenylbutoxy)-1,3-diphenyl-3-prop-1-enylamine
  参考文献：
  名称：

  Chiral Oxime Ethers in Asymmetric Synthesis. 3.¹ Asymmetric Synthesis of (R)-N-Protected α-Amino Acids by the Addition of Organometallic Reagents to the ROPHy Oxime of Cinnamaldehyde

  摘要：

  A new asymmetric synthesis of a-amino acids is described in which the key step is the diastereoselective addition of organometallic reagents to (R)-O-(1-phenylbutyl)cinnamaldoxime 5 to give hydroxylamines 6. Subsequent reductive cleavage of the N-O bond in the hydroxylamine 6 followed by N-protection gave the carbamates 7, which upon oxidation with ruthenium(III) chloride/periodate gave the N-protected amino acids 8. The method was also adapted to the synthesis of a quaternary amino acid 15 from the ketoxime ether 9.

  DOI：

  10.1021/jo9901079

文献信息

• Chiral oxime ethers in asymmetric synthesis. Part 5.1 Asymmetric synthesis of 2-substituted 5- to 8-membered nitrogen heterocycles by oxime addition–ring-closing metathesis
  作者：James C. A. Hunt、Pierre Laurent、Christopher J. Moody

  DOI：10.1039/b207235c

  日期：——

  Addition of organometallic reagents to chiral oxime ethers 1 derived from an unsaturated aldehyde, or addition of an alkene containing organometallic to chiral aldoxime ethers 2 results in highly stereoselective formation of the hydroxylamines 6. N-Allylation gives the dienes 7 which undergo ring-closing metathesis (RCM) reaction to give the 5-, 6-, and 7-membered nitrogen heterocycles 8. Likewise

  在手性化合物中添加有机金属试剂 肟 醚 1来自不饱和醛，或添加 烯烃 含有有机金属至手性 醛肟 醚 2导致高度立体选择性的形成羟胺 6。N-烯丙基化给出二烯7中经历闭环复分解 （RCM）反应生成5元，6元和7元 氮杂环8。同样地，氨基甲酸苄酯类9，也通过立体选择性除了肟醚制备，转化成二烯烃10，该例行RCM给出5到8元的azacycles 11。这肟 添加-RCM 因此，协议是非对称合成的通用方法 氮 杂环，进一步以不饱和杂环转化为手性为例 哌啶，包括生物碱（-）-coniine。
• Addition of Organolithiums to the (<i>R</i>)-<i>O</i>-(1-Phenylbutyl)hydroxylamine (ROPH_y) Oxime of Cinnamaldehyde. Asymmetric Synthesis of α-Aminoacids
  作者：Christopher Moody、Andrew Lightfoot、Peter Gallagher

  DOI：10.1055/s-1997-3252

  日期：1997.6

  A new asymmetric synthesis of α-aminoacids is described in which the key step is the diastereoselective addition of organolithium reagents to (R)-O-(1-phenylbutyl) cinnamaldoxime.

  描述了一种新的非对称合成α-氨基酸的方法，其中关键步骤是有机锂试剂对(R)-O-(1-苯基丁基)肉桂醛肟的二氟选择性加成。
• Asymmetric synthesis of 2-substituted 5-, 6- and 7-membered nitrogen heterocycles by oxime addition ring-closing metathesis
  作者：James C. A. Hunt、Pierre Laurent、Christopher J. Moody

  DOI：10.1039/b005353h

  日期：——

  Ring closing metathesis reactions of the dienes 6 and 9 leads to the nitrogen heterocycles 7 and 10, respectively, one of which 10c was converted into (R)-(−)-coniine.

  二烯 6 和 9 的闭环复分解反应分别产生氮杂环 7 和 10，其中一个 10c 被转化为 (R)-(-)-coniine。
• Chiral Oxime Ethers in Asymmetric Synthesis. 3.¹ Asymmetric Synthesis of (<i>R</i>)-N-Protected α-Amino Acids by the Addition of Organometallic Reagents to the ROPHy Oxime of Cinnamaldehyde
  作者：Christopher J. Moody、Peter T. Gallagher、Andrew P. Lightfoot、Alexandra M. Z. Slawin

  DOI：10.1021/jo9901079

  日期：1999.6.1

  A new asymmetric synthesis of a-amino acids is described in which the key step is the diastereoselective addition of organometallic reagents to (R)-O-(1-phenylbutyl)cinnamaldoxime 5 to give hydroxylamines 6. Subsequent reductive cleavage of the N-O bond in the hydroxylamine 6 followed by N-protection gave the carbamates 7, which upon oxidation with ruthenium(III) chloride/periodate gave the N-protected amino acids 8. The method was also adapted to the synthesis of a quaternary amino acid 15 from the ketoxime ether 9.