(-)-(2R,4R)-3-benzyl-2-methyl-4-phenyloxazolidine | 132273-88-2

• 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: (-)-(2R,4R)-3-benzyl-2-methyl-4-phenyloxazolidine
• 英文别名: (2R,4R)-3-benzyl-2-methyl-4-phenyl-1,3-oxazolidine
• CAS: 132273-88-2
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: XRVZBBHMVPWSGH-PBHICJAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  magnesium,methanidyl-dimethyl-propan-2-yloxysilane,chloride 、 (-)-(2R,4R)-3-benzyl-2-methyl-4-phenyloxazolidine 在 potassium fluoride 、 双氧水 、 碳酸氢钠 作用下， 生成 (1R,1'R)-N-benzyl-1-phenyl-1'-methyl-2,2'-dihydroxydiethylamine
  参考文献：
  名称：

  Stereoselective Synthesis of Optically Active Diethanolamines Utilizing Diastereoselective Reaction of 1,3-Oxazolidines with Grignard Reagents

  摘要：

  The highly diastereoselective addition of isopropoxydimethylsilylmethylmagnesium chloride to N-benzyl-1,3-oxazolidines derived from (R)-phenyl-glycinol, followed by oxidation of adducts with hydrogen peroxide in the presence of potassium fluoride, provided the 1-substituted (1R, 1'R)-N-benzyl-1'-phenyl-2,2'-dihydroxydiethylamines (1a-d).

  DOI：

  10.3987/com-95-7116
• 作为产物：
  描述：

  苯乙醇,b-[(苯基亚甲基)氨基]-,(R)- 在 sodium tetrahydroborate 、 3 A molecular sieve 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (-)-(2R,4R)-3-benzyl-2-methyl-4-phenyloxazolidine
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure α-Substituted Propargylic Amines by Reaction of Organoaluminum Reagents with Oxazolidines

  摘要：

  Various oxazolidines prepared in two steps from (R)-phenylglycinol react at 0 degrees C with dialkyl-alkynylalane-triethylamine complexes in the presence of trimethylaluminum in high yield and diastereoselectivity. Enantiomerically pure primary alpha-substituted propargylamines cah be easily obtained in two steps after removal of ferrocenylmethyl protective group under smooth acidic conditions and oxidative cleavage of the chiral appendage.

  DOI：

  10.1021/jo0003706

文献信息

• The absolute configuration and stereoselective grignard reaction of N-substituted 4-phenyl-1,3-oxazolidines.
  作者：Hiroshi TAKAHASHI、Bor Chyu-an HSIEH、Kimio HIGASHIYAMA

  DOI：10.1248/cpb.38.2429

  日期：——

  The configuration at the 2-position of 2-(p-bromophenyl)-N-methyl-4-phenyl-1, 3-oxazolidine (2a) was determined by X-ray analysis. The reactions of 2, 4-diphenyl- and 2-methyl-4-phenyl-1, 3-oxazolidines (2b-d and 2e-g) with methyl and phenylmagnesium bromides were investigated.

  通过X射线分析确定了2-(对溴苯基)-N-甲基-4-苯基-1,3-恶唑烷（2a）在2-位的构型。研究了2,4-二苯基-和2-甲基-4-苯基-1,3-恶唉烷（2b-d和2e-g）与甲基和苯基镁溴的反应。
• Stereoselective ring opening of chiral oxazolidines by reformatsky reagents: an enantioselective entry to β-amino esters.
  作者：Celia Andrés、Alfonso González、Rafael Pedrosa、Alfonso Pérez-Encabo

  DOI：10.1016/s0040-4039(00)78889-7

  日期：1992.5

  Chiral oxazolidines obtained by condensation of aldehydes with (-).(R)- or (+).(S)-N-benzylphenylglycinol react with the Reformatsky reagent derived from ethyl bromoacetate, in mild reaction conditions (Et2O or CH2Cl2, 0°C, 15-60 min), leading to ethyl β-amino carboxylates in moderate to good diastereomeric excess (60-92%). These ring opening products are transformed into primary β-aminoesters, in

  通过醛与（-）。（R）-或（+）。（S）-N-苄基苯基甘氨醇缩合获得的手性恶唑烷在温和的反应条件下（Et 2 O或CH 2 Cl 2，0℃，15-60分钟），从而导致乙基β-氨基羧酸盐在中度至良好的非对映体过量（60-92％）。通过在碳上用H 2 / Pd脱苄基化，一步就将这些开环产物转变成伯β-氨基酯。以此方式，可以两种对映体形式获得β-氨基羧酸乙酯，化学收率范围为55-76％和中等至良好的ee（60-92％）。
• Asymmetric Synthesis of α-Amino Phosphonic Acids by Diastereoselective Addition of Trimethyl Phosphite onto Chiral Oxazolidines¹
  作者：Catherine Maury、Tawfik Gharbaoui、Jacques Royer、Henri-Philippe Husson

  DOI：10.1021/jo960020c

  日期：1996.1.1

  A simple and general asymmetric synthesis of alpha-amino phosphonic acids is described. The method involves the highly selective addition of trialkyl phosphite onto various chiral oxazolidines. Oxazaphosphorinanes thus obtained with an excellent diastereoselectivity furnish the corresponding (S)-alpha-substituted amino phosphonic acids in good overall yields and high ee (77-->97%) after simple deprotection

  描述了α-氨基膦酸的简单且一般的不对称合成。该方法涉及将亚磷酸三烷基酯高度选择性地添加到各种手性恶唑烷上。如此获得的具有出色的非对映选择性的草氮磷杂环丁烷在简单的脱保护后以良好的总收率和较高的ee（77-> 97％）提供了相应的（S）-α-取代的氨基膦酸。
• Diastereoselective alkynylation of chiral non-racemic oxazolidines with mixed organoaluminum compounds
  作者：Jérôme Blanchet、Martine Bonin、Angèle Chiaroni、Laurent Micouin、Claude Riche、Henri-Philippe Husson

  DOI：10.1016/s0040-4039(99)00328-7

  日期：1999.4

  A new efficient and scalable route to chiral non-racemic α-substituted propargylamines is described. The reaction pathway consists of the diastereoselective addition of mixed alkynylaluminum reagents to oxazolidines derived from R-(−)-phenylglycinol.

  描述了一种新的有效且可扩展的途径来制备手性非外消旋α-取代的炔丙基胺。该反应途径包括将混合的炔基铝试剂非对映选择性地加至衍生自R -（-）-苯基甘氨醇的恶唑烷。
• TAKAHASHI, HIROSHI;HSIEH, BOR CHYU-AN;HIGASHIYAMA, KIMIO, CHEM. AND PHARM. BULL., 38,(1990) N, C. 2429-2434
  作者：TAKAHASHI, HIROSHI、HSIEH, BOR CHYU-AN、HIGASHIYAMA, KIMIO

  DOI：——

  日期：——