(R)-1-(2-羟基-1-苯乙基)-1,5-二氢吡咯-2-酮 | 158271-95-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (R)-1-(2-羟基-1-苯乙基)-1,5-二氢吡咯-2-酮
• 中文别名: (R)-1-(2-羟基-1-苯基乙基)-1,5-二氢吡咯-2-酮
• 英文名称: 1-(2-hydroxy-1-phenylethyl)-1,5-dihydropyrrol-2-one
• 英文别名: (R)-1-(2-Hydroxy-1-phenylethyl)-1H-pyrrol-2(5H)-one；1-[(1R)-2-hydroxy-1-phenylethyl]-2H-pyrrol-5-one
• CAS: 158271-95-5
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: IPPHIZDKNVGDJX-NSHDSACASA-N

物化性质

• 熔点：
  103 °C
• 沸点：
  341.55°C (rough estimate)
• 密度：
  1.1255 (rough estimate)
• 稳定性/保质期：
  遵循规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2933990090
• 储存条件：
  存放在阴凉干燥处即可。

SDS

MSDS英文版

反应信息

• 作为反应物：
  描述：

  (R)-1-(2-羟基-1-苯乙基)-1,5-二氢吡咯-2-酮 在 amberlyst-15 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以100%的产率得到(3R-顺)-(-)-3-苯基四氢吡咯并-[2,1-B]唑-5(6H)-酮
  参考文献：
  名称：

  Asymmetric synthesis of 5-substituted pyrrolidinones via a chiral N-acyliminium equivalent

  摘要：

  5-Substituted pyrrolidinones 5 were synthesized in good yields and with fair to good diastereoselectivities from the chiral non-racemic oxazolopyrrolidinone 4. Various nucleophiles including cuprates, silanes and phosphites were used. The chiral induction is thought to arise from a chelated N-acyliminium species. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00195-1
• 作为产物：
  描述：

  2,5-二甲氧基-2,5-二氢呋喃 、 (S)-(+)-1-苯基-1,2-乙二醇 在 盐酸 作用下， 反应 3.0h， 以75%的产率得到(R)-1-(2-羟基-1-苯乙基)-1,5-二氢吡咯-2-酮
  参考文献：
  名称：

  Diastereoselective bis-alkylation of chiral non-racemic α,β-unsaturated γ-lactams

  摘要：

  A new chiral non-racemic gamma-lactam 1 easily prepared in one step from (R)-(-)-phenylglycinol was bis-alkylated alpha to the carbonyl function in very high to complete diastereoselectivity. The stereochemistry at the so-formed chiral quaternary center was ascertained through an X-ray crystallographic study.

  DOI：

  10.1016/s0040-4039(00)76705-0

文献信息

• Asymmetric Routes Towards Polyfunctionalized Pyrrolidines: A Short Diastereoselective Synthesis of Polyhydroxylated Pyrrolidines and an Indolizidine
  作者：Bruno Dudot、Laurent Micouin、Isabelle Baussanne、Jacques Royer

  DOI：10.1055/s-1999-3434

  日期：1999.4

  Various (2S,3S,4R)-2-[(1R)-1-hydroxyalkyl]pyrrolidine-3,4-diols (11) have been prepared in 8 steps and 13-20% overall yields starting from (R)-(-)-phenylglycinol. This concise approach is based on the condensation of a chiral silyloxypyrrole with aldehydes which gave the (R,R)-aldol compounds in good yields and high diastereoselectivities. The cis-hydroxylation followed by reduction and deprotection gave the desired trihydroxylated pyrrolidines. The same strategy has been successively applied to a formal synthesis of 8a-epi-swainsonine.

  从(R)-(-)-苯甘氨醇出发，通过8步反应制备了各种(2S,3S,4R)-2-[(1R)-1-羟基烷基]吡咯烷-3,4-二醇(11)，总收率13-20%。这种简洁的方法是基于手性硅氧基吡咯与醛的缩合，从而得到(R,R)-醛缩化合物，收率高且立体选择性高。顺式羟基化后还原和脱保护得到所需的三羟基吡咯烷。同样的策略已成功应用于8a-表斯温森碱的正式合成。
• Asymmetric synthesis of 3-substituted pyrrolidones via α-alkylation of a chiral non-racemic γ-lactam
  作者：Isabelle Baussanne、Catherine Travers、Jacques Royer

  DOI：10.1016/s0957-4166(98)00024-x

  日期：1998.3

  3-Alkyl pyrrolidones 9 were synthesized in good yield and high diastereoselectivity by oc-alkylation of the new chiral non-racemic lactam 8 derived from (R)-(-)-phenylglycinol. After debenzylation and introduction of an electron-withdrawing group, 3-methylpyrrolidone 10 is easily hydrolyzed in a basic medium to produce gamma-aminobutyric acid (GABA) analogue 13. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Baussanne Isabelle, Chiaroni Angele, Husson Henri-Philippe, Riche Claude,+, Tetrahedron Lett, 35 (1994) N 23, S 3931-3934
  作者：Baussanne Isabelle, Chiaroni Angele, Husson Henri-Philippe, Riche Claude,+

  DOI：——

  日期：——
• Diastereoselective bis-alkylation of chiral non-racemic α,β-unsaturated γ-lactams
  作者：Isabelle Baussanne、Angèle Chiaroni、Henri-Philippe Husson、Claude Riche、Jacques Royer

  DOI：10.1016/s0040-4039(00)76705-0

  日期：1994.6

  A new chiral non-racemic gamma-lactam 1 easily prepared in one step from (R)-(-)-phenylglycinol was bis-alkylated alpha to the carbonyl function in very high to complete diastereoselectivity. The stereochemistry at the so-formed chiral quaternary center was ascertained through an X-ray crystallographic study.
• Asymmetric synthesis of 5-substituted pyrrolidinones via a chiral N-acyliminium equivalent
  作者：Isabelle Baussanne、Angèle Chiaroni、Jacques Royer

  DOI：10.1016/s0957-4166(01)00195-1

  日期：2001.5

  5-Substituted pyrrolidinones 5 were synthesized in good yields and with fair to good diastereoselectivities from the chiral non-racemic oxazolopyrrolidinone 4. Various nucleophiles including cuprates, silanes and phosphites were used. The chiral induction is thought to arise from a chelated N-acyliminium species. (C) 2001 Elsevier Science Ltd. All rights reserved.