(3R,7S,10R,14S)-7,14-Dimethoxy-3,10-diphenyl-1,8-dioxa-4,11-diaza-cyclotetradecane-5,12-dione | 195524-06-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (3R,7S,10R,14S)-7,14-Dimethoxy-3,10-diphenyl-1,8-dioxa-4,11-diaza-cyclotetradecane-5,12-dione
• 英文别名: (3R,7S,10R,14S)-7,14-dimethoxy-3,10-diphenyl-1,8-dioxa-4,11-diazacyclotetradecane-5,12-dione
• CAS: 195524-06-2
• 化学式: C₂₄H₃₀N₂O₆
• 分子量: 442.512
• InChiKey: HXODSRZTSVGHOH-TZYAJKAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  95.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,7S,10R,14S)-7,14-Dimethoxy-3,10-diphenyl-1,8-dioxa-4,11-diaza-cyclotetradecane-5,12-dione 在 红铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 96.0h， 以43%的产率得到N-((1R)-2-hydroxy-1-phenylethyl)-3-methoxy-3-(2-methoxyethoxy)-propanamide
  参考文献：
  名称：

  Studies on the Selective Reduction of the Amide Link of Acyclic and Macrocyclic Amidoketals: Unexpected Cleavage and trans‐Acetalization with Red‐Al^®

  摘要：

  Selective reduction of the amide moiety of acyclic and macrocyclic amido-ketals was studied in presence of various reagents (BH3 center dot Me2S, iBuAIH(2), Red-Al(R), LiAIH(4)). The best results were obtained with lithium aluminium hydride in the presence of triethylamine traces, whereas borane dimethyl sulfide gave rise to a partial ketal reduction of the acyclic compound and Red-Ale to a cleavage of the macrocyclic molecule accompanied by an unexpected traps-acetalization.

  DOI：

  10.1080/00397910701569478
• 作为产物：
  描述：

  3，3-二甲氧基丙酸甲酯 在 potassium cyanide 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 120.0h， 生成 (3R,7S,10R,14S)-7,14-Dimethoxy-3,10-diphenyl-1,8-dioxa-4,11-diaza-cyclotetradecane-5,12-dione
  参考文献：
  名称：

  A new and rapid access to a 14-membered diketal dilactam ring

  摘要：

  Macrocyclic dioxadilactam 2 was obtained in two steps from R-(-)-phenylglycinol via the chiral amido-ketal 1. Cyclization of 1 in acidic conditions (PTS A) and concentrated solution (c = 0.15 M) afforded 2 as three diasteromers 2a+2b+2c, two of which show a C-2 symmetry. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01282-3

文献信息

• Macrocyclic 14-Membered Ring Diketal Diamines: Synthesis, Conformational Analysis and99mTc Radiolabeling Evaluation
  作者：Radouane Affani、Philippe Auzeloux、Jean-Claude Madelmont、Denise Dugat

  DOI：10.1002/ejoc.200701151

  日期：2008.4

  corresponding diketal dilactams by reduction with lithium aluminum hydride in the presence of a trace amount of triethylamine. In the (15–30) × 10–3M concentration range, the reaction led mainly to the expected doubly reduced compounds except in the trans-OMe substituted series (R = Ph, Me), in which it partially stopped at the single reduction stage. A conformational study conducted by liquid NMR spectroscopy

  手性和非手性大环二缩酮二胺，环烷烃的类似物，是由先前获得的相应二缩酮二内酰胺在痕量三乙胺存在下用氢化铝锂还原合成的。在 (15–30) × 10–3M 浓度范围内，反应主要导致预期的双还原化合物，但反式 OMe 取代系列（R = Ph，Me）除外，其中它在单还原阶段部分停止. 通过液体核磁共振光谱和分子力学计算进行的构象研究表明，对于反式 OMe 化合物 7b (R = Me) 和 10b (R = H)，最稳定的构象要么设置在矩形 [3434] 型结构中，要么是稳定的由两个分子内 NH···O 氢键连接所有其他大环二胺。Tc-99m 用氮化锝核 [TcN]2+ 进行放射性标记，交换产率约为 10-20%。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Macrocyclic 14‐Membered‐Ring Diketal Dilactams: Spectroscopic Studies and Conformational Analysis of Their Complexes with Divalent Cations
  作者：Anne‐Gaëlle Valade、Dominique Harakat、Jacques Guyot、Olivier Laprévote、Denise Dugat

  DOI：10.1002/ejic.201000060

  日期：2010.7

  The complexation behaviour of four new 14-membered-ring diketal dilactam macrocycles towards some divalent cation perchlorates has been investigated. Stoichiometries and binding constants were determined by 1H NMR titration experiments. The structures of the complexes were studied by IR, NMR (1H and 13C) and electrospray mass spectrometry. 13C longitudinal relaxation time data allowed identification

  已经研究了四种新的 14 元环二缩酮双内酰胺大环化合物对某些二价阳离子高氯酸盐的络合行为。化学计量和结合常数通过 1 H NMR 滴定实验确定。通过IR、NMR（1H和13C）和电喷雾质谱法研究了配合物的结构。13C 纵向弛豫时间数据允许识别参与络合的供体原子，并提供有关络合配体分子内迁移率的信息。分子建模还用于进一步了解这些分子由于金属连接而发生的构象变化。发现 i. 大环以 Sr2+ Ca2+ > Mg2+ > Ba2+ 的结合顺序形成基本上 1:1 化学计量的复合物，ii．配位过程引起构象变化，导致配体结构中的氢键断裂和 NH-CO 键的新取向和 iii。阳离子的配位要么涉及配体的所有六个氧原子，要么涉及其中的五个，这取决于 OMe 基团是顺式还是反式，可能还有来自 ClO4 抗衡阴离子的两个氧原子。
• Bis-14-membered ring diketal diamines: Synthesis and evaluation of their anti-HIV and anti-tumoral activities
  作者：Radouane Affani、Franck Pélissier、Anne-Marie Aubertin、Denise Dugat

  DOI：10.1016/j.ejmech.2009.03.008

  日期：2009.8

  analogs of bicyclam AMD 3100, were synthesized in three steps from the previously obtained 14-membered ring diketal dilactams. Their monoreduction with lithium aluminium hydride gave the corresponding diketal aminolactams. Coupling these with dibromo-p-xylene led to xylyl dimer compounds. A second reduction step yielded the expected bis-diketal diamines in the methyl and unsubstituted series. Biological

  从先前获得的14元环双缩酮双内酰胺中分三步合成了手足和非手性大环双-二酮二胺，即双环酰胺AMD 3100的类似物。它们用氢化铝锂单还原得到相应的二缩酮氨基内酰胺。将它们与二溴对二甲苯偶联会生成二甲苯基二聚体化合物。第二还原步骤产生了预期的甲基和未取代系列的双-二缩二胺。对未还原和还原的二聚体的生物学测试显示，双-二苯基二缩酮氨基内酰胺13b的抗HIV和抗增殖活性均较弱，其作用方式可能与AMD 3100不同。
• A new and rapid access to a 14-membered diketal dilactam ring
  作者：Denise Dugat、Angèle Chiaroni、Claude Riche、Jacques Royer、Henri-Philippe Husson

  DOI：10.1016/s0040-4039(97)01282-3

  日期：1997.8

  Macrocyclic dioxadilactam 2 was obtained in two steps from R-(-)-phenylglycinol via the chiral amido-ketal 1. Cyclization of 1 in acidic conditions (PTS A) and concentrated solution (c = 0.15 M) afforded 2 as three diasteromers 2a+2b+2c, two of which show a C-2 symmetry. (C) 1997 Published by Elsevier Science Ltd.
• Studies on the Selective Reduction of the Amide Link of Acyclic and Macrocyclic Amidoketals: Unexpected Cleavage and <i>trans</i>‐Acetalization with Red‐Al^®
  作者：Radouane Affani、Denise Dugat

  DOI：10.1080/00397910701569478

  日期：2007.10.1

  Selective reduction of the amide moiety of acyclic and macrocyclic amido-ketals was studied in presence of various reagents (BH3 center dot Me2S, iBuAIH(2), Red-Al(R), LiAIH(4)). The best results were obtained with lithium aluminium hydride in the presence of triethylamine traces, whereas borane dimethyl sulfide gave rise to a partial ketal reduction of the acyclic compound and Red-Ale to a cleavage of the macrocyclic molecule accompanied by an unexpected traps-acetalization.