(1R,2S)-1-phenyl-2-benzyloxycarbonylamino-1-propanol | 104863-92-5

• 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: (1R,2S)-1-phenyl-2-benzyloxycarbonylamino-1-propanol
• 英文别名: (1R,2S)-N-benzyloxycarbonyl norephedrine；(1R,2S)-N-benzyloxycarbonylnorephedrine；L-N-benzyloxycarbonyl-norephedrine；N-carbobenzyloxy-norephedrine；benzyl N-[(1R,2S)-1-hydroxy-1-phenylpropan-2-yl]carbamate
• CAS: 104863-92-5
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: YBGZXXDWHAPAMW-BBRMVZONSA-N

物化性质

• 熔点：
  115-116 °C
• 沸点：
  477.0±45.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S)-1-phenyl-2-benzyloxycarbonylamino-1-propanol 在 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (1S,2S)-2-甲氨基-1-苯基丙-1-醇
  参考文献：
  名称：

  A new facile diastereoconversion of 2-amino alcohols involving a novel cyclocarbamation

  摘要：

  DOI：

  10.1016/s0040-4039(01)91366-8
• 作为产物：
  描述：

  benzyl [(1S)-1-methyl-2-oxo-2-phenylethyl]carbamate 在 三乙基硅烷 、 三氟乙酸 作用下， 以62%的产率得到(1R,2S)-1-phenyl-2-benzyloxycarbonylamino-1-propanol
  参考文献：
  名称：

  A new facile diastereoconversion of 2-amino alcohols involving a novel cyclocarbamation

  摘要：

  DOI：

  10.1016/s0040-4039(01)91366-8

文献信息

• Allylic stereocenter directed asymmetric conjugate addition of cuprates in the presence of trimethylchlorosilane. enantioselective synthesis of 2-alkyl-4-benzyioxybutanal and 2-alkyl-4-oxopentanal
  作者：Silvia Cardani、Giovanni Poli、Carlo Scolastico、Roberto Villa

  DOI：10.1016/s0040-4020(01)81451-4

  日期：1988.1

  Cuprate reagents in the presence of trimethylchlorosilane add with excellent Tr-face selectivity and yield to α,β-unsafcurated ketone and aldehyde bearing In γ-position a masked aldehyde represented by the C-2 of a norephedrine-derlved oxazolidine. The title compounds are obtained in high enantlomeric excess after removal of the chiral auxiliary and of the protective group.

  在三甲基氯硅烷存在下的铜酸盐试剂具有极佳的Tr-face选择性，并生成α，β-不饱和的酮和带有醛的醛。在γ-位置上，由去氧麻黄碱衍生的恶唑烷的C-2代表被掩盖的醛。除去手性助剂和保护基后，以高对映体过量得到标题化合物。
• A General and Expeditious One-Pot Synthesis of Sulfoxides in High Optical Purity from Norephedrine-Derived Sulfamidites
  作者：José L. García Ruano、Carlos Alemparte、M. Teresa Aranda、María M. Zarzuelo

  DOI：10.1021/ol027232i

  日期：2003.1.1

  A general and simple procedure for preparing any kind of enantiomerically enriched sulfoxide starting from norephedrine-derived N-benzyloxycarbonylsulfamidite 3a is reported. After one-pot reaction of 3a with RMgX, HBF(4), and R'MgX, a variety of sulfoxides 6 are obtained in ee usually higher than 93% and isolated yields ranging between 50 and 78%. The obtained configuration is tunable by simply electing

  报道了一种从降麻黄碱衍生的N-苄氧基羰基亚磺酰胺3a开始制备任何种类的对映体富集的亚砜的通用且简单的方法。3a与RMgX，HBF（4）和R'MgX进行一锅反应后，在ee中获得的多种亚砜6通常高于93％，分离出的产率在50％至78％之间。通过简单地选择试剂的添加顺序就可以调整获得的配置。[反应-见文字]
• Highly Diastereoselective Catalytic Meerwein−Ponndorf−Verley Reductions
  作者：Jingjun Yin、Mark A. Huffman、Karen M. Conrad、Joseph D. Armstrong

  DOI：10.1021/jo052121t

  日期：2006.1.1

  practical synthesis of ephedrine analogues in high yields and enantiopurity was realized by a highly diastereoselective Meerwein−Ponndorf−Verley (MPV) reduction of protected α-amino aromatic ketones using catalytic aluminum isopropoxide. The high anti selectivity resulted from the chelation of the nitrogen anion to the aluminum. In contrast, high syn selectivity was obtained with α-alkoxy ketones and other

  麻黄碱类似物的高收率和对映体纯度非常实用的合成，是通过使用催化异丙醇铝对非对映选择性的Meerwein-Ponndorf-Verley（MPV）还原保护的α-氨基芳族酮实现的。高抗选择性是由于氮阴离子与铝的螯合所致。相比之下，通过Felkin-Ahn对照品，可通过α-烷氧基酮和其他化合物获得高顺式选择性。
• A diastereoselective approach to enantiopure 3-substituted pyrrolidines from masked lithium homoenolates derived from norephedrine
  作者：María García-Valverde、Rafael Pedrosa、Martina Vicente、S. García-Granda、A. Gutiérrez-Rodríguez

  DOI：10.1016/0040-4020(96)00598-4

  日期：1996.8

  N-alkoxycarbonyl-2-(2′-bromoethyl)oxazolidines derived from norephedrines are transformed into lithium derivatives by reaction with 1 or 2 equiv of tert-butyllithium in Et2O. The lithium intermediates readily cyclize to bicyclic lactams that react with acetaldehyde and benzaldehyde leading to the addition products in excellent chemical yields and moderate diastereoselectivities. Removal of the chiral appendage provides

  通过与1或2当量的叔丁基锂在Et 2 O中反应，将衍生自去氧麻黄碱的N-烷氧基羰基-2-（2'-溴乙基）恶唑烷转化为锂衍生物。苯甲醛导致加成产物具有优异的化学收率和适度的非对映选择性。除去手性附肢可提供对映体纯的3-取代的吡咯烷。
• Norephedrine-derived 2-alkenyloxazolidines: stereochemistry of cyclization and allylic stereocenter directed asymmetric conjugate addition
  作者：Anna Bernardi、Silvia Cardani、Tullio Pilati、Giovanni Poli、Carlo Scolastico、Roberto Villa

  DOI：10.1021/jo00243a002

  日期：1988.4