(3S,5S)-3-(2-methylallyl)-5-phenylmorpholin-2-one | 881099-31-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,5S)-3-(2-methylallyl)-5-phenylmorpholin-2-one
• 英文别名: (3S,5S)-3-(2-methylprop-2-enyl)-5-phenylmorpholin-2-one
• CAS: 881099-31-6
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: NTCQMEPNIJAMKF-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,5S)-3-(2-methylallyl)-5-phenylmorpholin-2-one 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 生成 (4S,8R,9aS)-8-Bromomethyl-8-methyl-1-oxo-4-phenyl-6-thioxo-hexahydro-pyrimido[6,1-c][1,4]oxazine-7-carboxylic acid benzyl ester
  参考文献：
  名称：

  New Utilizations of Optically Active Homoallylamines: Highly Stereoselective Synthesis of Cyclic Guanidine and Thiourea

  摘要：

  DOI：

  10.3987/com-05-s(k)43
• 作为产物：
  描述：

  L-苯甘氨醇 在 indium 、 4 A molecular sieve 、 溶剂黄146 作用下， 以 甲醇 、 甲苯 、 苯 为溶剂， 生成 (3S,5S)-3-(2-methylallyl)-5-phenylmorpholin-2-one
  参考文献：
  名称：

  New Utilizations of Optically Active Homoallylamines: Highly Stereoselective Synthesis of Cyclic Guanidine and Thiourea

  摘要：

  DOI：

  10.3987/com-05-s(k)43

文献信息

• A Stereoselective aza-Prins Reaction: Rapid Access to Enantiopure Piperidines and Pipecolic Acids
  作者：Ramana Reddy Mittapalli、Simon J. Coles、Wim T. Klooster、Adrian P. Dobbs

  DOI：10.1021/acs.joc.0c01897

  日期：2021.2.5

  aza-Prins reaction is a widely employed and highly efficient method for the preparation of saturated nitrogen-containing heterocycles. Its major drawback has always been a lack of diastereoselectivity and the formation of racemic products. Herein, we address these problems and report, for the first time, the synthesis of both diastereomerically and enantiopure multiply substituted piperidines via the aza-Prins

  氮杂-普林斯反应是制备饱和含氮杂环的一种广泛采用的高效方法。其主要缺点一直是缺乏非对映选择性和外消旋产物的形成。本文中，我们解决了这些问题，并首次报告了通过aza-Prins反应合成非对映异构和对映纯的多取代哌啶的方法。该方法广泛适用于天然产物的合成，并在此以对映纯的胡椒酸衍生物的合成为例。
• The Asymmetric Aza-silyl-Prins Reaction: Synthesis of Enantiopure Piperidines
  作者：Ramana R. Mittapalli、Sebastien J. J. Guesné、Robert J. Parker、Wim T. Klooster、Simon J. Coles、John Skidmore、Adrian P. Dobbs

  DOI：10.1021/acs.orglett.8b03283

  日期：2019.1.18

  The design and development of the first asymmetric aza-silyl-Prins reaction is reported, giving rise to valuable and diverse piperidines and pipecolic acid derivatives in both high yields and as single enantiomers. The creation of a novel chiral auxiliary-homoallylic amine for the aza-silyl-Prins reaction is essential to its success.

  据报道，第一个不对称氮杂-甲硅烷基-Prins反应的设计和开发，以高收率和单一对映异构体的形式产生了有价值且多样的哌啶和哌考酸衍生物。对于氮杂-甲硅烷基-Prins反应而言，新型手性辅助-均烯丙基胺的产生对于其成功是至关重要的。
• Allyl Silane Additions to Highly Electrophilic 5,6-Dihydro-2H-1,4- oxazinones
  作者：Cynthia Shafer、Julie Pigza、Tadeusz Molinski

  DOI：10.2174/157017809787893046

  日期：2009.4.1

  Allylsilane addition to the dihydro-2H-1,4-oxazinones, 1, proceeded in moderate to good yields with transdiastereoselectivity. The yield of addition reactions of 5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one with allylsilanes is improved over the corresponding additions of Grignard reagents to 1 and illustrates a simple path to protected β,β- disubstituted α-amino acids.

  烯丙基硅烷对二氢-2H-1,4-恶嗪酮 1 的加成反应具有中等至良好的产率和反式对映选择性。5-苯基-5,6-二氢-2H-1,4-恶嗪-2-酮与烯丙基硅烷的加成反应的收率比格氏试剂与 1 的相应加成反应的收率要高，说明了一种获得受保护的 β、β- 二取代 α-氨基酸的简单途径。
• Diastereoselective Allylstannane Additions to (<i>S</i>)-5,6-Dihydro-2<i>H</i>-5-phenyloxazin-2-one. A Concise Synthesis of (<i>S</i>)-β-Methylisoleucine
  作者：Julie A. Pigza、Tadeusz F. Molinski

  DOI：10.1021/ol1001126

  日期：2010.3.19

  The addition of allyl stannanes to (S)-4,5-dihydro-5-phenyl-2H-oxazinone (3) was achieved under Bronsted acid catalysis to give 2-allylmorpholinones with high diastereoselectivity (up to dr 14.2:1). The product of dimethylallyltributylstannane addition to 3 was converted to L-beta-methylisoleucine, an alpha-amino acid residue found in the complex, biologically active marine-derived peptides polytheonamides A and B, and polydiscamides A-C.