S(+)-N-tert-butyl-O-acetyl mandelamid | 469874-36-0

• 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: S(+)-N-tert-butyl-O-acetyl mandelamid
• 英文别名: [(1S)-2-(tert-butylamino)-2-oxo-1-phenylethyl] acetate
• CAS: 469874-36-0
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: BOVCFKRFRLLZFA-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  S(+)-N-tert-butyl-O-acetyl mandelamid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以96%的产率得到(S)-(+)-2-叔-丁基氨基-1-苯基乙醇
  参考文献：
  名称：

  Synthesis of chiral non-racemic 1,2-diamines from O-acetyl mandelic acid: application in enantioselective deprotonation of epoxides and diethylzinc addition to aldehydes

  摘要：

  A variety of 1,2-diamines were synthesized from readily available O-acetyl mandelic acid. These diamines were used in the synthesis of key intermediates for the preparation of (-)-utenone A and carbovir involving enantioselective deprotonation of epoxides, The addition of Et2Zn catalysed by some of these diamines was also studied and although ees were not high, some interesting observations were made in the outcome of the stereochemistry of the product. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00376-9
• 作为产物：
  描述：

  (S)-(+)-扁桃酸 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 copper dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 S(+)-N-tert-butyl-O-acetyl mandelamid
  参考文献：
  名称：

  Synthesis of chiral non-racemic 1,2-diamines from O-acetyl mandelic acid: application in enantioselective deprotonation of epoxides and diethylzinc addition to aldehydes

  摘要：

  A variety of 1,2-diamines were synthesized from readily available O-acetyl mandelic acid. These diamines were used in the synthesis of key intermediates for the preparation of (-)-utenone A and carbovir involving enantioselective deprotonation of epoxides, The addition of Et2Zn catalysed by some of these diamines was also studied and although ees were not high, some interesting observations were made in the outcome of the stereochemistry of the product. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00376-9

文献信息

• Silica gel-immobilised chiral 1,2-benzenedisulfonimide: a Brønsted acid heterogeneous catalyst for enantioselective multicomponent Passerini reaction
  作者：Achille Antenucci、Francesco Marra、Stefano Dughera

  DOI：10.1039/d1ra05297g

  日期：——

  A chiral heterogeneous catalyst derivative of (−)-4,5-dimethyl-3,6-bis(1-naphthyl)-1,2-benzenedisulfonimide is proven here to be efficient in a three-component asymmetric Passerini protocol, carried out in a deep eutectic solvent. Reaction conditions are mild and green, while enantioselectivity is excellent. The catalyst was easily recovered and reused with no decrease in its catalytic activity.

  (-)-4,5-dimethyl-3,6-bis(1-naphthyl)-1,2-benzodisulfonimide 的手性多相催化剂衍生物在这里被证明在三组分不对称 Passerini 协议中是有效的，在一种低共熔溶剂。反应条件温和且绿色，对映选择性极佳。该催化剂易于回收和重复使用，其催化活性不降低。