(S)-N-benzyl-N-(1,3-diphenylprop-2-ynyl)hydroxylamine | 1022915-15-6

• 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: (S)-N-benzyl-N-(1,3-diphenylprop-2-ynyl)hydroxylamine
• 英文别名: N-benzyl-N-[(1S)-1,3-diphenylprop-2-ynyl]hydroxylamine
• CAS: 1022915-15-6
• 化学式: C₂₂H₁₉NO
• 分子量: 313.399
• InChiKey: CALJSYHCTYVCOF-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  (S)-N-benzyl-N-(1,3-diphenylprop-2-ynyl)hydroxylamine 在 palladium dihydroxide 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 (R)-N-benzyl-N-(1,3-diphenylpropyl)hydroxylamine
  参考文献：
  名称：

  Asymmetric addition of phenylzinc reagents to C-alkynyl nitrones. Enantiomeric enhancement by a product-like additive

  摘要：

  Asymmetric addition of diphenylzinc to C-alkynyl nitrones was achieved by utilizing di(t-butyl) (R,R)-tartrate as a chiral auxiliary to afford the corresponding optically active (S)-N-(1-phenyl-3-substituted prop-2-ynyl)hydroxylamines. By the addition of a product-like additive, enantiomeric enhancement was observed. A mixed zinc reagent, PhZnMe, improved the enantioselection to afford hydroxylamines in up to 92% ee. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.029
• 作为产物：
  描述：

  苯甲醛 在 N-benzyl-N-[1-(4-methoxyphenyl)-3-phenylprop-2-ynyl]hydroxylamine 、 (+)-二叔丁基 L-酒石酸 、 magnesium sulfate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 33.0h， 生成 (R)-N-benzyl-N-(1,3-diphenylprop-2-ynyl)hydroxylamine 、 (S)-N-benzyl-N-(1,3-diphenylprop-2-ynyl)hydroxylamine
  参考文献：
  名称：

  4-异恶唑啉的合成通过金（I） -催化的环化的炔Ñ -Hydroxylamines

  摘要：

  通过炔丙基N-羟胺的催化分子内环化，已经开发了用于合成4-异恶唑啉的新的催化方法。在存在5 mol％（PPh 3）AuCl / 5 mol％AgOTf或5 mol％（PPh 3）AuNTf 2的情况下，反应在室温下不到1小时内即可快速进行。该方法具有高产率，短反应时间和温和反应条件的高效合成4-异恶唑啉的途径。

  DOI：

  10.1021/acs.joc.6b01499

文献信息

• Catalytic Asymmetric Addition of Alkynylzinc Reagents to Nitrones
  作者：Atsuko Konishi、Weilin Wei、Masato Kobayashi、Shuhei Fujinami、Yutaka Ukaji、Katsuhiko Inomata

  DOI：10.1246/cl.2007.44

  日期：2007.1

  The catalytic asymmetric addition of alkynylzinc reagents, which were prepared in situ from dimethylzinc and 1-alkynes, to nitrones was achieved by utilizing di(t-butyl) (R,R)-tartrate as a chiral ...

  通过利用二（叔丁基）（R，R）-酒石酸盐作为手性物质，实现了由二甲基锌和 1-炔烃原位制备的炔基锌试剂与硝酮的催化不对称加成反应。
• Asymmetric Addition of Alkynylzinc Reagents to Nitrones Utilizing Tartaric Acid Ester as a Chiral Auxiliary
  作者：Weilin Wei、Masato Kobayashi、Yutaka Ukaji、Katsuhiko Inomata

  DOI：10.1246/cl.2006.176

  日期：2006.2

  The asymmetric addition of alkynylzinc reagents, prepared in situ from dialkylzinc and 1-alkynes, to nitrones was achieved by utilizing di(t-butyl) (R,R)-tartrate as a chiral auxiliary to afford the corresponding optically active (R)-α-substituted propargylic N-hydroxylamines. By the addition of product-like N-hydroxylamine, unprecedented enhancement of enantioselectivity was observed to afford the

  由二烷基锌和 1-炔烃原位制备的炔基锌试剂与硝酮的不对称加成是通过使用二（叔丁基）（R，R）-酒石酸盐作为手性助剂来实现的，以提供相应的旋光性（R）- α-取代的炔丙基N-羟胺。通过添加类似产品的 N-羟胺，观察到对映选择性的前所未有的增强，以提供高达 95% ee 的 N-羟胺。
• Asymmetric addition of phenylzinc reagents to C-alkynyl nitrones. Enantiomeric enhancement by a product-like additive
  作者：Weilin Wei、Yoshihira Hamamoto、Yutaka Ukaji、Katsuhiko Inomata

  DOI：10.1016/j.tetasy.2008.01.029

  日期：2008.3

  Asymmetric addition of diphenylzinc to C-alkynyl nitrones was achieved by utilizing di(t-butyl) (R,R)-tartrate as a chiral auxiliary to afford the corresponding optically active (S)-N-(1-phenyl-3-substituted prop-2-ynyl)hydroxylamines. By the addition of a product-like additive, enantiomeric enhancement was observed. A mixed zinc reagent, PhZnMe, improved the enantioselection to afford hydroxylamines in up to 92% ee. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of 4-Isoxazolines through Gold(I)-Catalyzed Cyclization of Propargylic <i>N</i>-Hydroxylamines
  作者：B. Chandrasekhar、Sewon Ahn、Jae-Sang Ryu

  DOI：10.1021/acs.joc.6b01499

  日期：2016.8.5

  New catalytic methods for the synthesis of 4-isoxazolines have been developed via catalytic intramolecular cyclizations of propargylic N-hydroxylamines. The reactions proceed rapidly in less than 1 h at room temperature in the presence of 5 mol % (PPh3)AuCl/5 mol % AgOTf or 5 mol % (PPh3)AuNTf2. This process features an efficient route to 4-isoxazolines with high yields, short reaction times, and mild

  通过炔丙基N-羟胺的催化分子内环化，已经开发了用于合成4-异恶唑啉的新的催化方法。在存在5 mol％（PPh 3）AuCl / 5 mol％AgOTf或5 mol％（PPh 3）AuNTf 2的情况下，反应在室温下不到1小时内即可快速进行。该方法具有高产率，短反应时间和温和反应条件的高效合成4-异恶唑啉的途径。