2-(tert-butoxycarbonylamino)-3-tert-butoxypropanal | 174363-86-1

• 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: 2-(tert-butoxycarbonylamino)-3-tert-butoxypropanal
• 英文别名: tert-butyl N-[1-(tert-butoxy)-3-oxopropan-2-yl]carbamate；tert-butyl N-[1-[(2-methylpropan-2-yl)oxy]-3-oxopropan-2-yl]carbamate
• CAS: 174363-86-1
• 化学式: C₁₂H₂₃NO₄
• 分子量: 245.319
• InChiKey: NRADPBSNPKALLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(tert-butoxycarbonylamino)-3-tert-butoxypropanal 在 palladium on activated charcoal 正丁基锂 、 氢气 、 4-甲基苯磺酸吡啶 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 [3-(2-Amino-4-decyl-phenyl)-1-tert-butoxymethyl-propyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Designed molecules reproducing the two conformations of teleocidins.

  摘要：

  Tumor-promoting teleocidins are known to exist in an equilibrium between two conformational states, the twist form and sofa form, in solution. Benzolactam-Vs, in which the indole ring of indolactams was replaced with a benzene ring, were designed in an attempt to reproduce the active conformation of teleocidins, and synthesized. The 8-membered lactam (benzolactam-V8-310) exists only in the twist form in solution and the 9-membered lactam (benzolactam-V9-310) exists only in the sofa form in solution. The stronger biological activities of the 8-membered lactam than those of indolactam-V and the lack of activity of the 9-membered lactam clearly indicated that active conformation for tumor-promoting activity of teleocidins is close to the twist form.

  DOI：

  10.1016/s0040-4039(00)61468-5
• 作为产物：
  描述：

  (R)-methyl 2-(benzyloxycarbonylamino)-3-t-butoxypropanoate 在 二异丁基氢化铝 作用下， 生成 2-(tert-butoxycarbonylamino)-3-tert-butoxypropanal
  参考文献：
  名称：

  Designed molecules reproducing the two conformations of teleocidins.

  摘要：

  Tumor-promoting teleocidins are known to exist in an equilibrium between two conformational states, the twist form and sofa form, in solution. Benzolactam-Vs, in which the indole ring of indolactams was replaced with a benzene ring, were designed in an attempt to reproduce the active conformation of teleocidins, and synthesized. The 8-membered lactam (benzolactam-V8-310) exists only in the twist form in solution and the 9-membered lactam (benzolactam-V9-310) exists only in the sofa form in solution. The stronger biological activities of the 8-membered lactam than those of indolactam-V and the lack of activity of the 9-membered lactam clearly indicated that active conformation for tumor-promoting activity of teleocidins is close to the twist form.

  DOI：

  10.1016/s0040-4039(00)61468-5

文献信息

• Synthesis, Conformation, and Biological Activity of Teleocidin Mimics, Benzolactams. A Clarification of the Conformational Flexibility Problem in Structure−Activity Studies of Teleocidins
  作者：Yasuyuki Endo、Michihiro Ohno、Masaaki Hirano、Akiko Itai、Koichi Shudo

  DOI：10.1021/ja953578v

  日期：1996.1.1

  Tumor-promoter teleocidins and their active congeners (indolactams) are known to exist in an equilibrium between at least two conformational states in solution, the twist and sofa form, due to cis-trans isomerization of the amide bond and the steric effects of substituents on the nine-membered lactam ring. Benzolactam-Vs, in which the indole ring of indolactams is replaced with a benzene ring, were designed and synthesized in an attempt to reproduce the active conformation of teleocidins. Among these benzolactams, eight-membered lactams (benzolactam-V8) can only exist in the twist form, and 9- and 10-membered lactams (benzolactam-V9 and -V10) exist exclusively in the sofa form in solution. The stronger biological activity of benzolactam-V-8-310 than that of indolactam-V (IL-V) and the inactivity of benzolactam-V-9-310 for differentiation inducing activity of HL-60 clearly indicated that the twist form is close to the active conformation of teleocidins.
• Synthesis and antibacterial activity of alaremycin derivatives for the porphobilinogen synthase
  作者：Noritaka Iwai、Kyosuke Nakayama、Jumpei Oku、Tomoya Kitazume

  DOI：10.1016/j.bmcl.2011.03.106

  日期：2011.5

  The preparation and the antibacterial activity of alaremycin derivatives such as their CF(3)-derivatives and (R)- and (S)-4-oxo-5-acetylaminohexanoic acid for the porphobilinogen synthase (PBGS), were described. The IC(50) values of the antibacterial activity of the prepared materials for the inhibitor of PBGS, were determined using PBGS assay. (C) 2011 Elsevier Ltd. All rights reserved.
• Novel conformationally constrained analogues of diacylglycerol. Protein kinase C binding affinity of simplified compounds based on a 6-membered lactam moiety
  作者：Yasuyuki Endo、Masaaki Hirano、Paul E. Driedger、Silvia Stabel、Koichi Shudo

  DOI：10.1016/s0960-894x(97)10129-9

  日期：1997.12

  Four configurational isomers of 6-hydroxymethyl-3-isopropyl-4-tetradecylpiperazin-2-ones (4-7), which were designed based on information obtained from the biologically active conformation of teleocidins and benzolactams, were synthesized and evaluated for their ability to compete with [H-3]phorbol 12,13-dibutyrate in a PKC delta binding assay. Among the compounds, the 3S,6S-isomer (5) showed moderate binding affinity, 8-30 fold more potent than for the other isomers. This indicates that the relative position of the hydrogen-bonding sites and hydrophobic regions of 5 fits into the cavity of PKC delta binding site. Compound 5 provides a conformationally constrained analogue of diacylglycerol. (C) 1997 Elsevier Science Ltd.