(4R)-2-((E)-2-Phenylethenyl)-4-phenyl-1,3-oxazolidine | 138234-70-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4R)-2-((E)-2-Phenylethenyl)-4-phenyl-1,3-oxazolidine
• 英文别名: (4R)-4-phenyl-2-[(E)-2-phenylethenyl]-1,3-oxazolidine
• CAS: 138234-70-5
• 化学式: C₁₇H₁₇NO
• 分子量: 251.328
• InChiKey: UJJWLBZMQIBWOD-FSNYXLCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (4R)-2-((E)-2-Phenylethenyl)-4-phenyl-1,3-oxazolidine 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 生成 (S)-3-phenylheptan-1-ol
  参考文献：
  名称：

  1,2- vs. 1,4-addition of nucleophilic organometallics to nonracemic 2-(1-naphthyl)- and 2-cinnamyl-1,3-oxazolidines

  摘要：

  We herein report our results where the addition of organomagnesium reagents to 2-(1-naphthyl)- and 2-cinnamyl-1,3-oxazolidines occurred consistently in a 1,4-conjugate manner, while lithium, cerium, and copper organometallic reagents added in a 1,2-fashion. The 1,4-conjugate addition pathway was primarily exploited by using (4R)-2-(1-naphthyl)-4-phenyl-1,3-oxazolidine (4) as a substrate to obtain, after NaBH4 reduction of the intermediate aldehyde, trans-disubstituted 1,2-dihydronaphthalenes with enantiomeric excesses of 93-94%. The amino alcohol products resulting from 1,2-addition were oxidatively cleaved to afford enantiomeric enriched (R)-alpha-(1-naphthyl)alkylamines 6a and 6b in > 99% ee.

  DOI：

  10.1021/jo00030a035
• 作为产物：
  描述：

  反式肉桂醛 、 D-苯甘氨醇 在 magnesium sulfate 作用下， 以 氯仿 为溶剂， 以77%的产率得到(4R)-2-((E)-2-Phenylethenyl)-4-phenyl-1,3-oxazolidine
  参考文献：
  名称：

  1,2- vs. 1,4-addition of nucleophilic organometallics to nonracemic 2-(1-naphthyl)- and 2-cinnamyl-1,3-oxazolidines

  摘要：

  We herein report our results where the addition of organomagnesium reagents to 2-(1-naphthyl)- and 2-cinnamyl-1,3-oxazolidines occurred consistently in a 1,4-conjugate manner, while lithium, cerium, and copper organometallic reagents added in a 1,2-fashion. The 1,4-conjugate addition pathway was primarily exploited by using (4R)-2-(1-naphthyl)-4-phenyl-1,3-oxazolidine (4) as a substrate to obtain, after NaBH4 reduction of the intermediate aldehyde, trans-disubstituted 1,2-dihydronaphthalenes with enantiomeric excesses of 93-94%. The amino alcohol products resulting from 1,2-addition were oxidatively cleaved to afford enantiomeric enriched (R)-alpha-(1-naphthyl)alkylamines 6a and 6b in > 99% ee.

  DOI：

  10.1021/jo00030a035

文献信息

• A stereoselective concise synthesis of C2- and meso-aminodiols from (R)-phenylglycinol
  作者：Mark A. Scialdone、A.I. Meyers

  DOI：10.1016/s0040-4039(00)78336-5

  日期：1994.10

  Oxazolidines derived from (R)-phenylglycinol can undergo diastereoselective vinyl- and aryl addition to give, after oxidative cleavage, meso- and C2-diethanol amines.

  衍生自（R）-苯基甘醇的恶唑烷可经历非对映选择性的乙烯基和芳基加成反应，在氧化裂解后得到内消旋和C 2-二乙醇胺。
• Scialdone Mark A., Meyers A. I., Tetrahedron Lett., 35 (1994) N 41, S 7533-7536
  作者：Scialdone Mark A., Meyers A. I.

  DOI：——

  日期：——
• 1,2- vs. 1,4-addition of nucleophilic organometallics to nonracemic 2-(1-naphthyl)- and 2-cinnamyl-1,3-oxazolidines
  作者：Lendon N. Pridgen、Mohamed K. Mokhallalati、Ming Jung Wu

  DOI：10.1021/jo00030a035

  日期：1992.2

  We herein report our results where the addition of organomagnesium reagents to 2-(1-naphthyl)- and 2-cinnamyl-1,3-oxazolidines occurred consistently in a 1,4-conjugate manner, while lithium, cerium, and copper organometallic reagents added in a 1,2-fashion. The 1,4-conjugate addition pathway was primarily exploited by using (4R)-2-(1-naphthyl)-4-phenyl-1,3-oxazolidine (4) as a substrate to obtain, after NaBH4 reduction of the intermediate aldehyde, trans-disubstituted 1,2-dihydronaphthalenes with enantiomeric excesses of 93-94%. The amino alcohol products resulting from 1,2-addition were oxidatively cleaved to afford enantiomeric enriched (R)-alpha-(1-naphthyl)alkylamines 6a and 6b in > 99% ee.