O-tert-butyl-N,N'-dicyclohexylisourea | 50867-21-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: O-tert-butyl-N,N'-dicyclohexylisourea
• 英文别名: 2-tert-Butyl-1,3-dicyclohexylisourea；tert-butyl N,N'-dicyclohexylcarbamimidate
• CAS: 50867-21-5
• 化学式: C₁₇H₃₂N₂O
• 分子量: 280.454
• InChiKey: BHEKYOLNRIGGLB-UHFFFAOYSA-N

物化性质

• 沸点：
  426.0±12.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  33.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  O-tert-butyl-N,N'-dicyclohexylisourea 在 palladium on activated charcoal 氢气 、 N,N'-二环己基碳二亚胺 、 copper(l) chloride 作用下， 以 氯仿 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 72.0h， 生成 6',6''-di-tert-butyl-18β-glycyrrhizin
  参考文献：
  名称：

  Kanaoka, Matao; Yano, Saburo; Kato, Hiromi, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 6, p. 1866 - 1873

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N'-二环己基碳二亚胺 、 叔丁醇 在 copper(l) chloride 作用下， 反应 18.0h， 生成 O-tert-butyl-N,N'-dicyclohexylisourea
  参考文献：
  名称：

  ti化的肽。第11部分。[4- 3 H-Phe 6 ]-，[4- 3 H-Phe 11 ]-和[4- 3 H-Phe 6,11 ]-生长抑素和代谢物[des-Ala 1 ]的合成生长抑素

  摘要：

  合成方法描述了生长抑素+在位置6和11的苯丙氨酸残基中分别用tri标记，在残基6和11处分别用by标记，分别通过完全保护的还原性碘化反应使比放射性活度分别为15.5、13.8和14.1 Cim mol –1。前体。半胱氨酸残基受S-三苯甲基保护，二硫键由碘化oxidation化的受保护前体形成。通过酸性水解，离子交换和高压液相色谱，以及通过酶消化经还原和氨乙基化改性的产物，评估产物的纯度。描述了代谢物[des-Ala 1 ]-生长抑素的合成。[Phe（描述了I）6 ]-，[Phe（I）11 ]-和[Phe（I）6,11 ]-生长抑素。

  DOI：

  10.1039/p19810002040
• 作为试剂：
  描述：

  O-tert-butyl-N,N'-dicyclohexylisourea 、 6-(benzyloxy)-2,2-dimethylhexanoic acid 在 O-tert-butyl-N,N'-dicyclohexylisourea 作用下， 以72的产率得到6-benzyloxy-2,2-dimethylhexanoic acid tertbutyl ester
  参考文献：
  名称：

  [EN] CALCIUM DICARBOXYLATE ETHERS, METHODS OF MAKING SAME, AND TREATMENT OF VASCULAR DISEASE AND DIABETES THEREWITH
  [FR] ETHERS DE DICARBOXYLATE DE CALCIUM, LEURS PROCEDES DE FABRICATION ET LEUR UTILISATION DANS LE TRAITEMENT DES MALADIES VASCULAIRES ET DU DIABETE

  摘要：

  6-(5-羧基-5-甲基己氧基)-2,2-二甲基己酸单钙盐的酒精和水溶剂是结晶的，其化学式为（I），其中R1为氢或低碳基，x为0至10的数字，可用于治疗血脂异常。

  公开号：

  WO2001055078A1

文献信息

• Inhibitors of protein kinases
  申请人：Zeitlmann Lutz

  公开号：US20110224225A1

  公开（公告）日：2011-09-15

  Compounds of general Formula (I): wherein R 1 , R 2 , R 3 , R a , A, B and x are as defined herein are inhibitors of protein kinases in particular members of the cyclin-dependent kinase family and/or the glycogen synthase kinase 3 family and are useful in preventing and/or treating any type of pain, inflammatory disorders, cancer, immunological diseases, proliferative diseases, infectious diseases, cardiovascular diseases, metabolic disorders, renal diseases, neurologic and neuropsychiatric diseases and neurodegenerative diseases.

  通用式(I)的化合物： 其中R1、R2、R3、Ra、A、B和x的定义如本文所述，是特定于细胞周期蛋白激酶家族和/或糖原合成酶激酶3家族的抑制剂，并且在预防和/或治疗任何类型的疼痛、炎症性疾病、癌症、免疫性疾病、增殖性疾病、传染病、心血管疾病、代谢性疾病、肾脏疾病、神经和神经精神疾病以及神经退行性疾病方面具有用处。
• Studies on the enzyme immunoassay of bio-active constituents contained in oriental medicinal drugs. IV. Enzyme immunoassay of glycyrrhetic acid.
  作者：MATAO KANAOKA、SABURO YANO、HIROMI KATO、TAKAKO NAKADA、KAZUHIRO KAWAMURA

  DOI：10.1248/cpb.36.8

  日期：——

  Enzyme immunoassay of glycyrrhetic acid was developed by employing antisera elicited from in rabbits immunized with C-3 bridged glycyrrhetic acid-bovine serum albumin (BSA) conjugate (15, 16) and C-3 bridged glycyrrhetic acid-β-galactosidase conjugate (17, 18) as labeled antigens. Hemisuccinyl and hemiglutaryl groups, which were chosen as the chemical bridges, were introduced at the hydroxy group of tert-butyl glycyrrhetate (2). Immunoassay was performed with bridge heterologous combinations such as anti-glycyrrhetic acid-hemisuccinate-BSA (15) antiserum and glycyrrhetic acid-hemiglutarate-β-galactosidase conjugate (18) and the reverse combination (16 and 17). The sensitivity of enzyme immunoassays (EIA) expressed as the midpoint (logit B/B0=0) was higher in the former combination (2.4 ng/tube) than the reverse combination (8.6 ng/tube). The cross reactivities of the anti-C-3 bridged glycyrrhetic acid antisera with C-3 substituted derivatives of glycyrrhetic acid were higher than those of the anti-C-30 bridged glycyrrhetic acid antiserum.

  利用由C-3桥联甘草次酸-牛血清白蛋白(BSA)偶联物(15, 16)和C-3桥联甘草次酸-β-半乳糖苷酶偶联物(17, 18)作为标记抗原，激发产生的兔抗血清，开发了甘草次酸的酶免疫分析方法。选择了半琥珀酰和半谷氨酰基团作为化学桥联，引入到叔丁基甘草次酸的羟基上(2)。通过桥联异源组合，如抗甘草次酸-半琥珀酸-BSA(15)抗血清和甘草次酸-半谷氨酸盐-β-半乳糖苷酶偶联物(18)以及反向组合(16和17)进行免疫测定。酶免疫分析(EIA)的灵敏度，以中点(logit B/B0=0)表示，在前一种组合(2.4 ng/管)中高于反向组合(8.6 ng/管)。抗C-3桥联甘草次酸抗血清与C-3取代的甘草次酸衍生物的交叉反应性高于抗C-30桥联甘草次酸抗血清。
• Photorelease of tyrosine from a-carboxy-6-nitroveratryl (aCNV) derivatives
  作者：Alexander G. Russell、Matthew J. Sadler、Helen J. Laidlaw、Agustín Gutiérrez-Loriente、Christopher W. Wharton、David Carteau、Dario M. Bassani、John S. Snaith

  DOI：10.1039/c2pp05320a

  日期：2012.3

  The synthesis of photolabile tyrosine derivatives protected on the phenolic oxygen by the α-carboxy-6-nitroveratryl (αCNV) protecting group is described. The compounds undergo rapid photolysis at wavelengths longer than 300 nm to liberate the corresponding phenol in excellent yield (quantum yield for the deprotection of tyrosine = 0.19). Further protection of caged tyrosine is possible, yielding N-Fmoc protected derivatives suitable for direct incorporation of caged tyrosine in solid-phase peptide synthesis.

  报道了通过α-羧基-6-硝基藜芦基（αCNV）保护基保护在酚羟基上的光不稳定性酪氨酸衍生物的合成。这些化合物在波长大于300 nm的光照射下迅速发生光解反应，以优异的产率释放相应的苯酚（酪氨酸去保护的量子产率为0.19）。还可以对笼蔽的酪氨酸进行进一步保护，得到适合直接用于固相肽合成的N-芴甲氧羰基保护衍生物。
• Studies on the enzyme immunoassay of bio-active constituents contained in oriental medicinal drugs. V. Preparation of bovine serum albumin conjugate and .BETA.-galactosidase labelled antigen for enzyme immunoassay of 3.BETA.-(monoglucuron-1'.BETA.-yl)-18.BETA.-glycyrrhetic acid.
  作者：Matao KANAOKA、Hiromi KATO、Saburo YANO

  DOI：10.1248/cpb.38.221

  日期：——

  In order to prepare an immunogen for enzyme immunoassay of 3β-(monoglucuron-1'-β-yl)-18β-glycyrrhetic acid (3MGA), which was isolated from a patient with glycyrrhizin-induced pseudoaldosteronisms, benzyl glycyrrhetate (3) was allowed to react with an acetobromosugar (2) in the presence of silver carbonate to give benzyl 3β-(methyl2', 3', 4'-triacetyl-glucuron-1'β-yl)-glycyrrhetate (5) and methyl 3', 4'-diacetyl-α-1', 2'-O-[1-(benzyl glycyrrhet-3β-yl)-ethylidene]-D-glucuronate (4). On the other hadn, this reaction was carried out in the presence of mercuric cyanide in nitromethane to give compound 5, benzyl 3β-acetryl glycyrrhetate (6) and benzyl 11-oxo-A-neooleana-3(5), 12-dien-3-oate (7). 4-Aminomethylcyclohexanecarboxylic acid and glycine were introduced as chemical bridges at C-30 of 3β-(tertbutylglucuron-1'β-yl)-glycyrrhetic acid (11) derived from compound 5. The former bridge was used to prepare an immunogenic conjugate with bovine serum albumin, and the latter bridge was used for antigen labelled with β-galactosidase.

  为了制备酶联免疫测定 3β-(单葡糖醛酸-1'-β-基)-18β-甘草亭酸（3MGA）的免疫原，该免疫原是从一名甘草苷诱发的假醛固酮症患者体内分离出来的、在碳酸银存在下，甘草酸苄酯（3）与乙酰溴糖（2）发生反应，生成 3β-（甲基 2'，3'、4'-三乙酰基-葡萄糖醛酸-1'β-基）-甘草酸苄酯 (5) 和 3'，4'-二乙酰基-α-1'，2'-O-[1-(甘草酸苄酯-3β-基)-亚乙基]-D-葡萄糖醛酸甲酯 (4)。另一方面，在硝基甲烷中存在氰化汞的情况下进行该反应，得到化合物 5、3β-乙酰甘草酸苄酯 (6) 和 11-氧代-A-neooleana-3(5), 12-二烯-3-油酸苄酯 (7)。4-Aminomethylcyclohexanecarboxylic acid（4-氨基甲基环己烷羧酸）和甘氨酸被引入到由化合物 5 衍生的 3β-(叔丁基葡萄糖醛酸-1'β-基)-甘草亭酸（11）的 C-30 处作为化学桥。前一个桥用于制备与牛血清白蛋白的免疫原轭合物，后一个桥用于制备与 β-半乳糖苷酶标记的抗原。
• The Synthesis of (2<i>S</i>)-4,4-Difluoroglutamyl γ-Peptides Based on Garner’s Aldehyde­ and Fluoro-Reformatsky Chemistry
  作者：James K. Coward、David W. Konas、Jessica J. Pankuch

  DOI：10.1055/s-2002-35616

  日期：——

  development of optically active fluorinated synthetic building blocks of general utility is a current goal of organofluorine chemists. The serine-derived Garner aldehyde was converted to a general 4,4-difluoroamino acid building block via fluoro-Reformatsky reaction with ethyl bromodifluoroacetate. The utility of this building block was demonstrated by the synthesis of derivatives of(2S)-4,4-difluoroglutamine

  开发具有通用性的光学活性氟化合成构件是有机氟化学家当前的目标。丝氨酸衍生的加纳醛通过与溴二氟乙酸乙酯的氟-Reformatsky 反应转化为通用的 4,4-二氟氨基酸结构单元。通过合成 (2S)-4,4-二氟谷氨酰胺、(2S)-4,4-二氟谷氨酸的衍生物并将其掺入设计为机械探针的含荧光团异肽 2 中，证明了该构件的实用性γ-谷氨酰水解酶。化合物 2 被证明是 γ-谷氨酰水解酶的底物，其水解速度明显低于相应的非氟化类似物。