[(2S,3S)-3-(dibenzylamino)-1-iodo-4-phenylbutan-2-yl] acetate | 199125-42-3

• 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: [(2S,3S)-3-(dibenzylamino)-1-iodo-4-phenylbutan-2-yl] acetate
• CAS: 199125-42-3
• 化学式: C₂₆H₂₈INO₂
• 分子量: 513.418
• InChiKey: KWZSCODKPVSKCE-IZZNHLLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(2S,3S)-3-(dibenzylamino)-1-iodo-4-phenylbutan-2-yl] acetate 在 锌 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 以82%的产率得到(S)-N,N-dibenzyl-1-phenylbut-3-en-2-amine
  参考文献：
  名称：

  Iodomethylation of Chiral α-Amino Aldehydes by Means of Samarium/Diiodomethane. Application to the Synthesis of Various Enantiomerically Pure Compounds

  摘要：

  Chiral iodohydrins 2 have been obtained from alpha-amino aldehydes 1 and Sm/CH2I2. Treatment of compound 2 with acetic anhydride, NaH, or AgBF4 affords, with high diastereoselectivity, O-protected 3-(dibenzylamino)-1-iodoalkan-2-ol 3, amino epoxides 4, or azetidinium salts 5, respectively. The synthesis of enantiomerically pure allylamines 6 is also described by metallation of 3 with zinc. The reaction of a-amino aldehydes 1 with Sm/CH2I2 and further treatment with organocuprates affords chiral amino alcohols 7 in a one-pot process.

  DOI：

  10.1021/jo970318i
• 作为产物：
  描述：

  苯丙醛,a-[二(苯基甲基)氨基]-,(S)- 在 4-二甲氨基吡啶 、 三氢化钐 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 [(2S,3S)-3-(dibenzylamino)-1-iodo-4-phenylbutan-2-yl] acetate
  参考文献：
  名称：

  Iodomethylation of Chiral α-Amino Aldehydes by Means of Samarium/Diiodomethane. Application to the Synthesis of Various Enantiomerically Pure Compounds

  摘要：

  Chiral iodohydrins 2 have been obtained from alpha-amino aldehydes 1 and Sm/CH2I2. Treatment of compound 2 with acetic anhydride, NaH, or AgBF4 affords, with high diastereoselectivity, O-protected 3-(dibenzylamino)-1-iodoalkan-2-ol 3, amino epoxides 4, or azetidinium salts 5, respectively. The synthesis of enantiomerically pure allylamines 6 is also described by metallation of 3 with zinc. The reaction of a-amino aldehydes 1 with Sm/CH2I2 and further treatment with organocuprates affords chiral amino alcohols 7 in a one-pot process.

  DOI：

  10.1021/jo970318i

文献信息

• Nucleophilic ring closure and opening of aminoiodohydrins
  作者：José M Concellón、Pablo L Bernad、Juan A Pérez-Andrés

  DOI：10.1016/s0040-4039(99)02250-9

  日期：2000.2

  Enantiopure aminoiodohydrins obtained from a-aminoaldehydes and Sm/CH2I2 have been transformed into regioisomeric aminoiodohydrins, aminoepoxides, azetidines or 1,3-oxazolidines. The key step in these transformations is a nucleophilic opening-closing process. (C) 2000 Elsevier Science Ltd. All rights reserved.