(4R)-2-(1-萘基)-4-苯基-1,3-恶唑烷 | 252864-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: (4R)-2-(1-萘基)-4-苯基-1,3-恶唑烷
• 英文名称: 2-(1-naphthyl)-4-(4R)-phenyl-1,3-oxazolidine
• 英文别名: (R)-2-naphthyl-4-phenyl-1,3-oxazolidine；(4R)-2-(1-Naphthyl)-4-phenyl-1,3-oxazolidine；(4R)-2-naphthalen-1-yl-4-phenyl-1,3-oxazolidine
• CAS: 252864-72-5
• 化学式: C₁₉H₁₇NO
• 分子量: 275.35
• InChiKey: QOBMAXCQZVIZGR-OYKVQYDMSA-N

物化性质

• 沸点：
  462.8±33.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 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-(1-萘基)-4-苯基-1,3-恶唑烷 在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 (1R,2S)-(+)-trans-1-(Hydroxymethyl)-2-butyl-1,2-dihydronaphthalene
  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：

  D-苯甘氨醇 、 1-萘甲醛 在 magnesium sulfate 作用下， 以 氯仿 为溶剂， 以75%的产率得到(4R)-2-(1-萘基)-4-苯基-1,3-恶唑烷
  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

• An efficient enantiomeric three step synthesis of β-amino acids (esters)
  作者：Mohamed K. Mokhallalati、Ming-Jung Wu、Lendon N. Pridgen

  DOI：10.1016/s0040-4039(00)60054-0

  日期：1993.1

  Ethyl tributylstannylacetate was reacted with (R)-2-aryl or alkyl-1,3-oxazolidines 6 under very specific (ZnCl2/Et2O·BF3, 0.5 equiv each) Lewis Acid catalysed conditions to yield (1R, 1′R)-N-2′-hydroxy-1′-phenylethyl-1-aryl or alkyl-2-carboethoxyethylamine 8 in 91–99% de. The amino alcohol products 8 were converted to aromatic and aliphatic β-amino esters 9, useful precursors to β-lactams.

  在非常特定的（ZnCl 2 / Et 2 O·BF 3，各0.5当量）路易斯酸催化条件下，使三丁基锡锡乙酸乙酯与（R）-2-芳基或烷基1，，3-恶唑烷6反应，得到（1R，1' R）-N-2'-羟基-1'-苯基乙基-1-芳基或烷基-2-羰基乙氧基乙胺8在91–99％de中。将氨基醇产物8转化为芳族和脂族β-氨基酯9，它们是β-内酰胺的有用前体。
• A novel stereo- and enantioselective synthesis of trans-9-alkyl-2-benzyl-5-methyl-6,7-benzomorphans
  作者：Ali Dehghani、Xu Bai、S.Wayne Mascarella、Wayne D. Bowen、F.Ivy Carroll

  DOI：10.1016/0040-4039(94)88402-1

  日期：1994.11

  The first stereo- and enantioselective syntheses of trans-9-alkyl-2-benzyl-5-methyl-6,7-benzomorphans (12) are described. The addition of alkyl magnesium halides to (R)-2-naphthyl-4-phenyl-1,3-oxazolidine (7) followed by treatment with iodomethane and quenching with acid gave (1S,2S)-2-alkyl-1-methyl-1,2-dihydronaphthalenecarboxaldehyde (10). Homologation of 10 followed by reductive amination using

  描述了反式-9-烷基-2-苄基-5-甲基-6,7-苯并吗啡喃的第一立体和对映选择性合成（12）。向（R）-2-萘-4-苯基-1,3-恶唑烷（7）中添加烷基卤化镁，然后用碘代甲烷处理并用酸淬灭，得到（1S，2S）-2-烷基-1 -甲基-1，2-二氢萘甲醛（10）。10的同系化，然后使用苄胺进行还原胺化，得到（1 S，2 S）-反式-2-烷基-1-苄基氨基乙基-1-甲基-1,2-二氢萘（11）。乙酸汞辅助环化的11随后通过LAH还原得到（1 S，5 S，9 R）-12。
• A single-pot synthesis of 1,1,2-trisubstituted 1,2-dihydronaphthalenes in high enantiomeric purity
  作者：Mohamed K Mokhallalati、K.Raman Muralidharan、Lendon N Pridgen

  DOI：10.1016/s0040-4039(00)73330-2

  日期：1994.6

  followed by electrophilic trapping of the azaenolate is described. This tandem addition was performed in a single flask producing 1,1,2-trisubstituted 1,2-dihydronaphthalenes 7 in excellent yields and high enantioselectivities.

  描述了将格氏试剂非对映选择性地添加到非外消旋的2-（1-萘基）-4-（4R）-苯基-1,3-恶唑烷（1）中，然后亲电捕获氮杂烯酸酯。该串联添加在单个烧瓶中进行，该烧瓶以优异的产率和高对映选择性生产1,1,2-三取代的1,2-二氢萘7。
• Asymmetric Synthesis of 9-Alkyl-2-benzyl-6,7-benzomorphans:  Characterization as Novel σ Receptor Ligands
  作者：F. Ivy Carroll、Xu Bai、Ali Dehghani、S. Wayne Mascarella、Wanda Williams、Wayne D. Bowen

  DOI：10.1021/jm990169r

  日期：1999.11.1

  A convenient enantioselective synthesis of (1R,5R,9R)- and (1S,5S,9S)-9-alkyl-2-benzyl-6,7-benzomorphans (2a-c) which starts with naphthaldehyde is described. These compounds were designed to gain additional information on the structure-a binding relationship of the 6,7-benzomorphan class of a ligands. In contrast to pentazocine and most 6,7-benzomorphans, the (1R,5R,9R)-isomers of 2a-c showed greater affinity for the al receptor than the (1S,5S,9S)isomers. Despite reversal of enantioselectivity at the ax sites, moderate affinity and enantioselectivity at the sigma(2) sites [greater affinity for (1R,5R,9R)-isomers than (1S,5S,9S)-isomers] were maintained. A comparison of the binding affinities of 2a-e to the more conformationally flexible trans-2-alkyl-1-benzaminoethyl-1,2-dihydronaphthalenes (10a-c) suggested that the relatively rigid structure of 2a-c played an important part in their al binding properties. These compounds, particularly (1R,5R,SR)-2-benzyl-9-methyl-6,7-benzomorphan [(-)-2a], which has a Ki value of 0.96 nM, will be useful in further characterization of the al receptor.
• WU, MING-JUNG;PRIDGEN, LENDON N., SYNLETT.,(1990) N0, C. 636-639
  作者：WU, MING-JUNG、PRIDGEN, LENDON N.

  DOI：——

  日期：——