benzyl (2S,1'R,3'R)-3-(tert-butoxycarbonyl)-2-(2',2'-dimethyl-3'-carboxycyclobutyl)propylcarbamate | 1138793-52-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl (2S,1'R,3'R)-3-(tert-butoxycarbonyl)-2-(2',2'-dimethyl-3'-carboxycyclobutyl)propylcarbamate
• CAS: 1138793-52-8
• 化学式: C₂₃H₃₃NO₆
• 分子量: 419.518
• InChiKey: OTPRYADETNEKQS-KURKYZTESA-N

物化性质

• 沸点：
  566.7±35.0 °C(predicted)
• 密度：
  1.146±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  101.93
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  benzyl (2S,1'R,3'R)-3-(tert-butoxycarbonyl)-2-(2',2'-dimethyl-3'-carboxycyclobutyl)propylcarbamate 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 (3S)-tert-butyl 4-benzyloxycarbonylamino-3-((1R,3R)-3-hexadecylcarbamoyl-2,2-dimethylcyclobutyl)butanoate
  参考文献：
  名称：

  New chiral polyfunctional cyclobutane derivatives from (−)-verbenone: possible surfactant behaviour

  摘要：

  New enantiopure cyclobutane derivatives have been synthesized from a chiral precursor derived from (-)-verbenone. The cyclobutane moiety acts as a chiral platform to afford a gamma-amino acid function in a branched side-chain containing an additional stereogenic centre as well as additional C-6 or C-15-alkyl chains linked to the ring by means of an amine or an amide function. One of these compounds, obtained as a 1:2 mixture with its TFA salt has been investigated, suggesting behaviour as a good surfactant and its critical micellar concentration has been determined. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.05.007
• 作为产物：
  描述：

  tert-butyl (S)-3-[(1R,3R)-3-acetyl-2,2-dimethylcyclobutyl]-4-(benzyloxy-carbonylamino)butanoate 在 sodium hypobromide 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以100%的产率得到benzyl (2S,1'R,3'R)-3-(tert-butoxycarbonyl)-2-(2',2'-dimethyl-3'-carboxycyclobutyl)propylcarbamate
  参考文献：
  名称：

  Stereoselective synthesis of cyclobutyl γ-amino acids leading to branched peptides with a cyclobutane core

  摘要：

  Alternative synthetic routes are provided to synthesize gamma-amino acids in their free form or conveniently protected for their selective incorporation into ramified gamma-peptides with a cyclobutane core. The key synthetic-step involves the stereoselective conjugate addition of nitromethane to chiral cyclobutyl alkenoates prepared from (-)-verbenone. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.019

文献信息

• Synthesis of Chiral Cyclobutane Containing <i>C</i>₃-Symmetric Peptide Dendrimers
  作者：Raquel Gutiérrez-Abad、Ona Illa、Rosa M. Ortuño

  DOI：10.1021/ol1010664

  日期：2010.7.16

  Five new highly functionalized cyclobutane containing C3-symmetric peptide dendrimers have been synthesized through a convergent approach from 1,3,5-trisubstituted benzene and chiral γ,ε-amino diacid derivatives as well as a γ-tetrapeptide. The first example of the synthesis of N-centered amides by using 1,3,5-triaminobenzene and a carboxylic acid is reported.

  通过收敛方法，由1,3,5-三取代苯和手性γ，ε-氨基二酸衍生物以及γ-四肽合成了五种新型的高度官能化的含C 3-对称肽树状大分子。报道了通过使用1,3,5-三氨基苯和羧酸合成N-中心酰胺的第一个例子。