N,N'-di(1-adamantyl)malonodiamide | 162008-32-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N,N'-di(1-adamantyl)malonodiamide
• 英文别名: N,N'-di(1-adamantyl)malondiamide；N,N'-Di(1-adamantyl)malonamide；N,N'-diadamantylmalonamide；N,N'-bis(1-adamantyl)propanediamide
• CAS: 162008-32-4
• 化学式: C₂₃H₃₄N₂O₂
• 分子量: 370.535
• InChiKey: CMRBUYIVUMJAQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N'-di(1-adamantyl)malonodiamide 、 alkaline earth salt of/the/ methylsulfuric acid 在 四溴化碳 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 27.0h， 以8.48%的产率得到61-bis(1-adamantylcarbamoyl)-1,2-methano[60]fullerene
  参考文献：
  名称：

  Synthesis of 61-bis(1-adamantylcarbamoyl)-1,2-methano[60]fullerene and its antagonistic effect on haloperidol-induced catalepsy in mice

  摘要：

  The 61-bis(1-adamantylcarbamoyl)-1,2-methano[60]fullerene was synthesized from N,N'-di(1-adamantyl)malondiamide and C-60 in the presence of 1,8-diazabicyclo[5,4,0]-7-undecene. The intraperitoneal administration of this fullerene derivative (10 mg/kg) caused an antagonistic effect on hatoperidol-induced catalepsy in mice. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.053
• 作为产物：
  描述：

  N-Adamantan-1-yl-malonamic acid methyl ester 在 lithium hydroxide 、 2,2'-二硫二吡啶 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 39.0h， 生成 N,N'-di(1-adamantyl)malonodiamide
  参考文献：
  名称：

  Design and Synthesis of Calcium and Magnesium Ionophores Based on Double-Armed Diazacrown Ether Compounds and Their Application to an Ion Sensing Component for an Ion-Selective Electrode

  摘要：

  The double-armed diazacrown ethers, which have a base diazacrown ether ring with two diamide-type side chains, were designed and synthesized on the basis of the proposed molecular model for the novel neutral Ca2+ and Mg2+ ionophores. The potentiometric ion-selective electrodes were prepared with over 20 kinds of systematically synthesized diazacrown ether derivatives. The relationship between the molecular structures of the ionophores and the ion selectivities was fully discussed. The electrodes based on the 21- and 18-membered diazacrown ether derivatives possessing a glycolic diamide and malonic diamide in their side chains (K23E1 and K22B5) exhibited excellent Ca2+ and Mg2+ selectivities, respectively. The ion-selectivity features of the novel Ca2+ and Mg2+ ionophores supply important structural information about the design of host molecules for alkaline earth metal cations.

  DOI：

  10.1021/ac00098a016

文献信息

• Adamantylation and Adamantylalkylation of Amides, Nitriles and Ureas in Trifluoroacetic Acid
  作者：Elvira Shokova

  DOI：10.1055/s-1997-1304

  日期：1997.9

  A new preparative method for N-adamantylation of carboxylic acid amides, ureas and for C5-adamantylation of barbituric acid in trifluoroacetic acid (TFA) is proposed. Tertiary 1-adamantanols and 1-(1-adamantyl)alkanols were used as adamantylating agents. The reaction of 1-(1-adamantyl)alkanols with nitriles in TFA solution was employed for the first time for the preparation of N-[1-(1-adamantyl)alkyl]amides.

  提出了一种在三氟乙酸（TFA）中进行羧酸酰胺、脲的N-金刚烷基化和巴比妥酸的C5-金刚烷基化的新制备方法。使用了三级的1-金刚烷醇和1-(1-金刚烷基)烷醇作为金刚烷基化试剂。首次采用了1-(1-金刚烷基)烷醇与腈在TFA溶液中的反应来制备N-[1-(1-金刚烷基)烷基]酰胺。
• Shokova; Musulu, Tasula; Luzikov, Russian Journal of Organic Chemistry, 1999, vol. 35, # 6, p. 844 - 856
  作者：Shokova、Musulu, Tasula、Luzikov、Kovalev

  DOI：——

  日期：——
• Design and Synthesis of Calcium and Magnesium Ionophores Based on Double-Armed Diazacrown Ether Compounds and Their Application to an Ion Sensing Component for an Ion-Selective Electrode
  作者：Koji. Suzuki、Kazuhiko. Watanabe、Yukihiro. Matsumoto、Mitsuru. Kobayashi、Sayaka. Sato、Dwi. Siswanta、Hideaki. Hisamoto

  DOI：10.1021/ac00098a016

  日期：1995.1.15

  The double-armed diazacrown ethers, which have a base diazacrown ether ring with two diamide-type side chains, were designed and synthesized on the basis of the proposed molecular model for the novel neutral Ca2+ and Mg2+ ionophores. The potentiometric ion-selective electrodes were prepared with over 20 kinds of systematically synthesized diazacrown ether derivatives. The relationship between the molecular structures of the ionophores and the ion selectivities was fully discussed. The electrodes based on the 21- and 18-membered diazacrown ether derivatives possessing a glycolic diamide and malonic diamide in their side chains (K23E1 and K22B5) exhibited excellent Ca2+ and Mg2+ selectivities, respectively. The ion-selectivity features of the novel Ca2+ and Mg2+ ionophores supply important structural information about the design of host molecules for alkaline earth metal cations.
• Synthesis of 61-bis(1-adamantylcarbamoyl)-1,2-methano[60]fullerene and its antagonistic effect on haloperidol-induced catalepsy in mice
  作者：Manabu Nakazono、Shigeo Hasegawa、Tsuneyuki Yamamoto、Kiyoshi Zaitsu

  DOI：10.1016/j.bmcl.2004.08.053

  日期：2004.11

  The 61-bis(1-adamantylcarbamoyl)-1,2-methano[60]fullerene was synthesized from N,N'-di(1-adamantyl)malondiamide and C-60 in the presence of 1,8-diazabicyclo[5,4,0]-7-undecene. The intraperitoneal administration of this fullerene derivative (10 mg/kg) caused an antagonistic effect on hatoperidol-induced catalepsy in mice. (C) 2004 Elsevier Ltd. All rights reserved.