2-[1-[[(1S)-1-(羟基甲基)-2-苯基乙基]氨基]乙亚基]-5,5-二甲基-1,3-环己烷二酮 | 302916-36-5

• 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: 2-[1-[[(1S)-1-(羟基甲基)-2-苯基乙基]氨基]乙亚基]-5,5-二甲基-1,3-环己烷二酮
• 英文名称: 2-[1-((1S)-hydroxymethyl-2-phenylethylamino)ethylidene]-5,5-dimethylcyclohexane-1,3-dione
• 英文别名: Dde-L-phenylalaninol；2-[1-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]ethylidene]-5,5-dimethylcyclohexane-1,3-dione
• CAS: 302916-36-5
• 化学式: C₁₉H₂₅NO₃
• 分子量: 315.412
• InChiKey: UURJFWXKCLQEPI-HNNXBMFYSA-N

物化性质

• 沸点：
  499.9±45.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.4
• 氢给体数：
  2.0
• 氢受体数：
  4.0

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  邻硝基苯磺酰氯 、 2-[1-[[(1S)-1-(羟基甲基)-2-苯基乙基]氨基]乙亚基]-5,5-二甲基-1,3-环己烷二酮 生成 (3S,6S)-3,6-dibenzylpiperazin-2-one
  参考文献：
  名称：

  The development and preparation of the 2,4-dimethoxybenzyl arylhydrazine (DMBAH) “latent” safety-catch linker: solid phase synthesis of ketopiperazines

  摘要：

  2,4-dimethoxybenzyl arylhydrazine (DMBAH) linker 3是一种新型 "钝性 "安全捕获连接体，在三忍烷基化条件下以及胺和肼的存在下都很稳定。利用环状裂解方法合成的酮基哌嗪（MKPs）24具有多达四个多样性点，充分体现了这种新型连接体的实用性。

  DOI：

  10.1039/b301701j
• 作为产物：
  描述：

  2-乙酰基-5,5-二甲基-1,3-环己二酮 、 L-苯丙氨醇 以 乙醇 为溶剂， 反应 3.0h， 以91%的产率得到2-[1-[[(1S)-1-(羟基甲基)-2-苯基乙基]氨基]乙亚基]-5,5-二甲基-1,3-环己烷二酮
  参考文献：
  名称：

  The development and preparation of the 2,4-dimethoxybenzyl arylhydrazine (DMBAH) “latent” safety-catch linker: solid phase synthesis of ketopiperazines

  摘要：

  2,4-dimethoxybenzyl arylhydrazine (DMBAH) linker 3是一种新型 "钝性 "安全捕获连接体，在三忍烷基化条件下以及胺和肼的存在下都很稳定。利用环状裂解方法合成的酮基哌嗪（MKPs）24具有多达四个多样性点，充分体现了这种新型连接体的实用性。

  DOI：

  10.1039/b301701j

文献信息

• Solid-Phase Synthesis, Hybridizing Ability, Uptake, and Nuclease Resistant Profiles of Position-Selective Cationic and Hydrophobic Phosphotriester Oligonucleotides
  作者：Luca Monfregola、Marvin H. Caruthers

  DOI：10.1021/acs.joc.5b01512

  日期：2015.9.18

  Analogues of oligonucleotides and mononucleotides with hydrophobic and/or cationic phophotriester functionalities often generate an improvement in target affinity and cellular uptake. Here we report the synthesis of phosphotriester oligodeoxyribonucleotides (ODNs) that are stable to the conditions used for their preparation. The method has been demonstrated by introducing phosphoramidite synthons where N-benzyloxycarbonyl (Z) protected amino alcohols replace the cyanoethyl group. After synthesis these ODNs were found to be stable to the condition required to remove base labile protecting groups and the ODNs from the solid support. Moreover the use of 1-(4,4-dimethyl-2, 6-dioxocyclohex-1-ylidene) ethyl (Dde) in place of Z protection on the amino alcohol has allowed us to introduce cationic aminoethyl phosphotriester modifications into ODNs. Melting temperatures of duplexes containing cationic or hydrophobic Z modified ODNs indicate that the backbone-phosphotriester modifications minimally affect duplex stability. Nuclease stability assays demonstrate that these phosphotriesters are resistant toward 5'- and 3'-exonudeases. Fluorescently labeled 23-mer ODNs modified with four cationic or hydrophobic Z phosphotriester linkages show efficient cellular uptake during passive transfection in HeLa and Jurkat cells.
• The synthesis of cyclic tetrapeptoid analogues of the antiprotozoal natural product apicidin
  作者：Peter J Murray、Michael Kranz、Mark Ladlow、Stephen Taylor、Frédéric Berst、Andrew B Holmes、Kenneth N Keavey、Albert Jaxa-Chamiec、Peter W Seale、Paul Stead、Richard J Upton、Simon L Croft、William Clegg、Mark R.J Elsegood

  DOI：10.1016/s0960-894x(01)00049-x

  日期：2001.3

  A novel synthetic strategy is described which may be used to prepare analogues of the antimalarial, fungal metabolite apicidin. Compared to the natural product, one analogue shows potent and selective activity in vitro against the parasite Trypanosoma brucei and low mammalian cell toxicity. (C) 2001 Elsevier Science Ltd. All rights reserved.
• A latent aryl hydrazine ‘safety-catch’ linker compatible with N-alkylation
  作者：Frédéric Berst、Andrew B Holmes、Mark Ladlow、Peter John Murray

  DOI：10.1016/s0040-4039(00)01108-4

  日期：2000.8

  The preparation and use of a latent aryl hydrazine 'safety-catch' linker for solid-phase chemistry, which is compatible with N-alkylation, is reported. Its use is exemplified by the preparation of mono-ketopiperazines, whereby release from resin is effected via an intramolecular cyclitive cleavage strategy. (C) 2000 Elsevier Science Ltd, All rights reserved.
• The development and preparation of the 2,4-dimethoxybenzyl arylhydrazine (DMBAH) “latent” safety-catch linker: solid phase synthesis of ketopiperazines
  作者：Frédéric Berst、Andrew B. Holmes、Mark Ladlow

  DOI：10.1039/b301701j

  日期：——

  The development and preparation of the 2,4-dimethoxybenzyl arylhydrazine (DMBAH) linker 3, a new class of “latent” safety-catch linker which is stable under Mitsunobu alkylation conditions and in the presence of amines and hydrazine, is reported. The utility of the new linker is exemplified by the synthesis of ketopiperazines (MKPs) 24 bearing up to four points of diversity using a cyclitive cleavage approach.

  2,4-dimethoxybenzyl arylhydrazine (DMBAH) linker 3是一种新型 "钝性 "安全捕获连接体，在三忍烷基化条件下以及胺和肼的存在下都很稳定。利用环状裂解方法合成的酮基哌嗪（MKPs）24具有多达四个多样性点，充分体现了这种新型连接体的实用性。