CBZ-D-苯甘氨醇 | 120666-53-7

• 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: CBZ-D-苯甘氨醇
• 中文别名: Cbz-(R)-苯甘氨醇
• 英文名称: (R)-benzyl (2-hydroxy-1-phenylethyl)carbamate
• 英文别名: (R)-benzyl [2-hydroxy-1-phenylethyl]carbamate；((R)-2-hydroxy-1-phenyl-ethyl)-carbamic acid benzyl ester；(R)-2-benzyloxycarbonylamino-2-phenylethanol；N-[(benzyloxy)carbonyl]-(R)-β-amino-2-phenylethanol；Cbz-(R)-2-phenylglycinol；benzyl N-[(1R)-2-hydroxy-1-phenylethyl]carbamate
• CAS: 120666-53-7
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: IWSCPMJLIZGTHY-HNNXBMFYSA-N

物化性质

• 沸点：
  469.7±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  CBZ-D-苯甘氨醇 在 ruthenium trichloride 氯化亚砜 、 吡啶 、 sodium periodate 、 水 作用下， 以 乙腈 为溶剂， 反应 1.02h， 以70%的产率得到(R)-3-(benzyloxycarbonyl)-4-phenyl-[1,2,3]oxathiazolidine 2,2-dioxide
  参考文献：
  名称：

  Synthesis of 2,6-Disubstituted Piperazines by a Diastereoselective Palladium-Catalyzed Hydroamination Reaction

  摘要：

  A highly diastereoselective intramolecular hydroamination is the key step in a modular synthesis of 2,6-disubstituted piperazines. The requisite hydroamination substrates were prepared in excellent yields by nucleophilic displacement of cyclic sulfamidates derived from amino acids. A variety of alkyl and aryl substituents at the 2-position were tolerated. The stereochemistry of the piperazines was determined to be trans by X-ray crystallography, which also showed the preferred conformation of the 2,6-disubstituted piperazine to be a twist-boat due to A(1,3) strain.

  DOI：

  10.1021/ol702891p
• 作为产物：
  描述：

  4-phenyl-2-oxazolidinone 在 sodium hydroxide 作用下， 生成 CBZ-D-苯甘氨醇
  参考文献：
  名称：

  脯氨酸催化曼尼希反应高对映选择性合成1,2-氨基醇衍生物

  摘要：

  在这里，我们报告了一种新的 oxazolidin-2-ones 4 和 Cbz 保护的 1,2-氨基醇 5 的催化不对称合成。 我们的序列基于先前未知的 5-acyloxy-oxazolidin-2-ones 的化学反应通过脯氨酸催化的直接不对称三组分曼尼希反应和 Baeyer-Villiger 氧化。

  DOI：

  10.1055/s-2003-41491

文献信息

• Substituted 5-membered ring heterocycles, their preparation and their use
  申请人：Hoechst Aktiengesellschaft

  公开号：US05981492A1

  公开（公告）日：1999-11-09

  The present invention pertains to 5-ring heterocycles of general formula (I), wherein W, Y, Z, B, D, E and R as well as b, c, d, e, f, g, and h are as indicated in the description; to methods for preparing them, and to their use as inhibitors of platelet aggregation, metastasizing of carcinomatous cells and the attachment of osteoclasts to the bone surface. ##STR1##

  本发明涉及一般式（I）的5-环杂环化合物，其中W、Y、Z、B、D、E和R以及b、c、d、e、f、g和h如描述中所示；以及其制备方法，以及它们作为抑制血小板聚集、癌细胞转移和破骨细胞附着于骨表面的用途。
• Synthesis of N-Vinyloxazolidinones and Morpholines from Amino Alcohols and Vinylsulfonium Salts: Analysis of the Outcome's Dependence on the N-Protecting Group by Nanospray Mass Spectrometry
  作者：Muhammad Yar、Sven P. Fritz、Paul J. Gates、Eoghan M. McGarrigle、Varinder K. Aggarwal

  DOI：10.1002/ejoc.201101272

  日期：2012.1

  in annulation reactions with diphenylvinylsulfonium triflate has been investigated. Although tosyl and sulfinamide groups give morpholines in high yields, the use of N-Cbz leads to a high-yielding synthesis of N-vinyloxazolidinones. The reactions were monitored by nanospray MS/MS, which revealed why reactions are successful and the fate of reactive intermediates in the unsuccessful reactions.

  已经研究了在与二苯基乙烯基锍三氟甲磺酸盐的成环反应中 N-保护基团的性质对 1,2-氨基醇的影响。尽管甲苯磺酰基和亚磺酰胺基团以高产率提供吗啉，但使用 N-Cbz 导致 N-乙烯基恶唑烷酮的高产率合成。通过纳米喷雾 MS/MS 监测反应，这揭示了反应成功的原因以及不成功反应中反应中间体的命运。
• Spiroimidazolidine derivatives, their preparation, their use and pharmaceutical preparations formed therefrom
  申请人：Aventis Pharma Deutschland GmbH

  公开号：US06399643B1

  公开（公告）日：2002-06-04

  The present invention relates to spiroimidazolidine derivatives of the formula I in which E, V, W, X, R1 and R2 have the meanings indicated in the claims. The compounds of the formula I are valuable pharmaceutical active compounds which are suitable, for example, for the therapy and prophylaxis of inflammatory disorders, such as, for example, rheumatoid arthritis, or allergic disorders. The compounds of the formula I are also inhibitors of the adhesion and migration of leukocytes and/or antagonists of the adhesion receptor VLA-4 belonging to the integrins group. They are generally suitable for the therapy and prophylaxis of illnesses which are caused by an undesired extent of leukocyte adhesion and/or leukocyte migration or are associated therewith or in which cell-cell or cell-matrix interactions which are based on interactions of VLA-4 receptors with their ligands play a part. The invention also relates to processes for the preparation of the compounds of the formula I, pharmaceutical preparations which contain compounds of the formula I, and methods for treating these disorders.

  本发明涉及式I的螺环咪唑啉衍生物，其中E、V、W、X、R1和R2具有索引中指示的含义。式I的化合物是有价值的药用活性化合物，例如适用于治疗和预防炎症性疾病，如风湿性关节炎或过敏性疾病。式I的化合物还是白细胞粘附和迁移的抑制剂和/或整合素群中属于VLA-4粘附受体的拮抗剂。它们通常适用于治疗和预防由白细胞粘附和/或白细胞迁移不受欢迎的程度引起的疾病，或与之相关的疾病，或在其中基于VLA-4受体与其配体相互作用的细胞-细胞或细胞-基质相互作用发挥作用的疾病。该发明还涉及制备式I的化合物的方法、含有式I的药物制剂以及治疗这些疾病的方法。
• Salts of ethyl 3-(2-(4-(4-amino-imino-methyl)phenyl)-4-methyl-2,5-dioxo-imidazolidin-1-yl)acetylamino)-3-phenylpropionate
  申请人：Hoechst Aktiengesellschaft

  公开号：US06294562B1

  公开（公告）日：2001-09-25

  The present invention relates to ethyl 3-(2-(4-(4-(amino-imino-methyl)-phenyl)-4-methyl-2,5-dioxoimidazolidin-1-yl)acetylamino)-3-phenylpropionate salts of the formula I, in which HM is maleic acid, and to their physiologically tolerated salts, thereof, to processes for their preparation and to their use in pharmaceuticals.

  本发明涉及式I的乙酸乙酯盐，其中HM为马来酸，以及其生理耐受盐，制备方法及在药物中的应用。
• Rationally designed "dipeptoid" analogs of CCK. .alpha.-Methyltryptophan derivatives as highly selective and orally active gastrin and CCK-B antagonists with potent anxiolytic properties
  作者：David C. Horwell、John Hughes、John C. Hunter、Martyn C. Pritchard、Reginald S. Richardson、Edward Roberts、Geoffrey N. Woodruff

  DOI：10.1021/jm00105a062

  日期：1991.1

  This paper describes the synthesis and structure-activity relationships (SAR) leading to the first rational design of "dipeptoid" analogues of the neuropeptide cholecystokinin (CCK). Compounds [R-(R*,S*)]-4-[2-[3-(1H-indol-3-yl)-2-methyl-1-oxo-2-[(tricyclo [3.3.1.1(3,7)]dec-2-yloxy)carbonyl]amino]propyl]amino]-3- phenylpropyl]-amino]-4-oxo-2-butenoic acid, [R-(R*,R*)]-4-[2-[3-(1H-indol-3-yl)-2-met

  本文介绍了合成和结构-活性关系（SAR），从而导致了神经肽胆囊收缩素（CCK）的“二肽”类似物的第一个合理设计。化合物[R-（R *，S *）]-4- [2- [3-（1H-吲哚-3-基）-2-甲基-1-氧代-2-[（三环[3.3.1.1（3 ，7）]癸-2-基氧基）羰基]氨基]丙基]氨基] -3-苯基丙基]-氨基] -4-氧代-2-丁烯酸，[R-（R *，R *）]-4- [2- [3-（1H-吲哚-3-基）-2-甲基-1-氧-2-（[三环[3.3.1.1（3,7）]癸-2-氧）羰基]氨基]丙基]氨基] -1-苯乙基]氨基] -4-氧代-2-丁烯酸和[R-（R *，R *）]-4- [2- [3-（1H-吲哚-3-基） -2-甲基-1-氧代-2-[（（三环[3.3.1.1（3,7）]癸-2-基氧基）羰基]氨基]丙基]氨基] -1-苯基乙基]氨基] -4-氧代丁酸（29d）的CCK-B结合亲和力IC50