tert-butyl N-[(3S,4R)-4-[(S)-hydroxy(phenyl)methyl]-2-methylhex-5-en-3-yl]carbamate | 477781-16-1

• 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: tert-butyl N-[(3S,4R)-4-[(S)-hydroxy(phenyl)methyl]-2-methylhex-5-en-3-yl]carbamate
• CAS: 477781-16-1
• 化学式: C₁₉H₂₉NO₃
• 分子量: 319.444
• InChiKey: QHKVUDOWHNRHPK-IXDOHACOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  tert-butyl N-[(3S,4R)-4-[(S)-hydroxy(phenyl)methyl]-2-methylhex-5-en-3-yl]carbamate 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 potassium carbonate 、 臭氧 、 三氟乙酸 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 水 、 叔丁醇 、 苯 为溶剂， 反应 3.17h， 生成 methyl (2R,3S)-2-[(S)-hydroxy(phenyl)methyl]-4-methyl-3-[(2,4,6-trimethylphenyl)sulfonylamino]pentanoate
  参考文献：
  名称：

  Asymmetric synthesis of β2,3-amino acids by InI–Pd(0)-promoted metalation and addition of chiral 2-vinylaziridines

  摘要：

  The reaction of optically active 3-alkyl-2-vinylaziridines with various aldehydes in the presence of InI and Pd(PPh3)(4) gives rise to chiral syn,syn-2-vinyl-1,3-amino alcohols possessing three contiguous chiral centers stereoselectively. The ratio of the syn,syn-isomer to the other three isomers is significantly affected by the C3-substituents of aziridines as well as the alkyl groups of aldehydes. In addition, the obtained 1,3-aminoalcohols can be converted into biologically important p(2,3)-amino acid derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00499-4
• 作为产物：
  描述：

  苯甲醛 、 tert-butyl (4S,5S)-5-ethenyl-2-oxo-4-propan-2-yl-1,3-oxazolidine-3-carboxylate 在 四(三苯基膦)钯 、 indium iodide 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到tert-butyl N-[(3S,4R)-4-[(S)-hydroxy(phenyl)methyl]-2-methylhex-5-en-3-yl]carbamate
  参考文献：
  名称：

  Asymmetric synthesis of β2,3-amino acids by InI–Pd(0)-promoted metalation and addition of chiral 2-vinylaziridines

  摘要：

  The reaction of optically active 3-alkyl-2-vinylaziridines with various aldehydes in the presence of InI and Pd(PPh3)(4) gives rise to chiral syn,syn-2-vinyl-1,3-amino alcohols possessing three contiguous chiral centers stereoselectively. The ratio of the syn,syn-isomer to the other three isomers is significantly affected by the C3-substituents of aziridines as well as the alkyl groups of aldehydes. In addition, the obtained 1,3-aminoalcohols can be converted into biologically important p(2,3)-amino acid derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00499-4

文献信息

• Stereoselective synthesis of nonracemic 1,3-amino alcohols from chiral 2-vinylaziridines by InI–Pd(0)-promoted metalation
  作者：Yoshiji Takemoto、Miyuki Anzai、Reiko Yanada、Nobutaka Fujii、Hiroaki Ohno、Toshiro Ibuka

  DOI：10.1016/s0040-4039(00)02334-0

  日期：2001.2

  Treatment of optically active 3-alkyl-2-vinylaziridines 1, 8 and 9 and allylic acetates 10 and 11 with InI in the presence of Pd(PPh3)(4) gives rise to chiral allylindiums bearing an amino group at the delta -position, which react with several aldehydes in highly regio- and stereoselective manner to afford the syn,syn-2-vinyl-1,3-amino alcohols 2a, 5a-7a and 12a-14a possessing three contiguous chiral centers in good yields. (C) 2001 Elsevier Science Ltd. All rights reserved.