N-carbobenzoxy-O-benzylhydroxylamine | 15255-86-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-carbobenzoxy-O-benzylhydroxylamine
• 英文别名: benzyloxyl carbamic acid benzyl ester；Benzyl (benzyloxy)carbamate；benzyl N-phenylmethoxycarbamate
• CAS: 15255-86-4
• 化学式: C₁₅H₁₅NO₃
• mdl: MFCD30569421
• 分子量: 257.289
• InChiKey: PIMQUYFJDPYHBL-UHFFFAOYSA-N

物化性质

• 熔点：
  64-65 °C(Solv: hexane (110-54-3))
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-carbobenzoxy-O-benzylhydroxylamine 在 氢溴酸 、 potassium carbonate 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 42.0h， 生成 Succinimido ester of N-methyl-N-(benzyloxy)succinamic acid
  参考文献：
  名称：

  Spermexatin and spermexatol: new synthetic spermidine-based siderophore analogs

  摘要：

  Syntheses of hexanediamine-based dihydroxamate (Hexamate), spermidine-based trihydroxamate (Spermexatins), and spermidine-based mixed siderophore analogues (Spermexatols) are described. Key intermediates include the N-hydroxysuccinimide esters of various hydroxamic acids, e.g., malonohydroxamate, succinohydroxamate, and glutarohydroxamate. These intermediates were synthesized, characterized, and incorporated as the ligating chains on spermidine. Also, mixed iron chelating compounds (Spermexatols) with both catechol and hydroxamic acid side chains were synthesized. The reagent carbobenzoxyimidazole was employed to distinguish between the primary and secondary amino groups of spermidine. The ability of these iron chelators to stimulate microbial growth is also described.

  DOI：

  10.1021/jm00122a013
• 作为产物：
  描述：

  苄氧基胺盐酸盐 、 氯甲酸苄酯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以85%的产率得到N-carbobenzoxy-O-benzylhydroxylamine
  参考文献：
  名称：

  乙二醛酶I的抑制作用：第一个低纳米摩尔紧密结合抑制剂。

  摘要：

  对已知的基于S-（N-芳基-N-羟基氨基甲酰基）谷胱甘肽的乙二醛酶I抑制剂的结构进行了一系列合理的修改，最终发现了第一个个位数的纳摩尔抑制剂。这项研究提供了有关解决困扰乙二醛酶I抑制区域的代谢不稳定，药效低和合成复杂性问题的可能手段的关键信息。从这项研究中获得的知识对具有更高构象定义和更低肽特性的抑制剂的设计具有重要意义。

  DOI：

  10.1021/jm900382u

文献信息

• [EN] MODULATORS OF THE INTEGRATED STRESS RESPONSE PATHWAY<br/>[FR] MODULATEURS DE LA VOIE DE RÉPONSE AU STRESS INTÉGRÉE
  申请人：EVOTEC INT GMBH

  公开号：WO2020216766A1

  公开（公告）日：2020-10-29

  The present invention relates to compounds of formula (I) or pharmaceutically acceptable salts, solvates, hydrates, tautomers or stereoisomers thereof, wherein R1, R2, R2a, R3, Ra2, Ra4, Ra5, Ra6, Ra7, X1, X1a, A1 and A2 have the meaning as indicated in the description and claims. The invention further relates to pharmaceutical compositions comprising said compounds, their use as medicament and in a method for treating and preventing of one or more diseases or disorders associated with integrated stress response.

  本发明涉及具有式（I）的化合物或其药学上可接受的盐、溶剂化合物、水合物、互变异构体或立体异构体，其中R1、R2、R2a、R3、Ra2、Ra4、Ra5、Ra6、Ra7、X1、X1a、A1和A2的含义如描述和权利要求中所示。该发明还涉及包含所述化合物的药物组合物，其用作药物以及用于治疗和预防与整合应激反应相关的一种或多种疾病或紊乱的方法。
• [EN] GONADOTROPIN RELEASING HORMONE RECEPTOR ANTAGONISTS, METHOD FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME<br/>[FR] ANTAGONISTES DES RÉCEPTEURS DE L'HORMONE DE LIBÉRATION DES GONADOTROPHINES, LEUR PROCÉDÉ DE PRÉPARATION ET COMPOSITION PHARMACEUTIQUE LES COMPRENANT
  申请人：SK CHEMICALS CO LTD

  公开号：WO2013129879A1

  公开（公告）日：2013-09-06

  The present invention provides gonadotropin releasing hormone receptor antagonists and the pharmaceutical composition comprising the same, which can be useful in preventing or treating a sex hormone-related disease such as endometriosis, amenorrhea, irregular menstruation, uterine myoma, uterine fibroids, polycystic ovarian disease, lupus erythematous, hypertrichosis, precocious puberty, short stature, acne, alopecia, gonadal steroid-dependent neoplasms, gonadotropin-producing pituitary adenoma, sleep apnea, irritable bowel syndrome, premenstrual syndrome, benign prostatic hyperplasia, contraception, and infertility, as well as Alzheimer disease.

  本发明提供了促性腺激素释放激素受体拮抗剂及包括其的药物组合物，可用于预防或治疗与性激素相关的疾病，如子宫内膜异位症、闭经、月经不调、子宫肌瘤、子宫肌瘤、多囊卵巢综合征、红斑狼疮、多毛症、性早熟、身材矮小、痤疮、脱发、性腺类固醇依赖性肿瘤、促性腺激素产生性垂体腺瘤、睡眠呼吸暂停、肠易激综合征、经前综合征、良性前列腺增生、避孕和不孕症，以及阿尔茨海默病。
• Interconversion of (R) and (S)-α-hydroxy esters: precursors of (S) and (R)-o-benzyl-α-hydroxylamino acid esters of high optical purity
  作者：R.W. Feenstra、E.H.M. Stokkingreef、R.J.F. Nivard、H.C.J. Ottenheijm

  DOI：10.1016/s0040-4020(01)86063-4

  日期：1988.1

  (R)- and (S)-α-hydroxy esters 5 are interconverted via their triflates 6 in high chemical as well as optical yields by reaction with dimethylformamide. The same triflates are efficiently converted into N-hydroxy-α-amino acid derivatives 7 of high optical purity.

  （R）-和（S）-α-羟基酯5通过它们的三氟甲磺酸酯6与二甲基甲酰胺反应以高化学产率和光学产率被转化。相同的三氟甲磺酸酯被有效地转化为高光学纯度的N-羟基-α-氨基酸衍生物7。
• GONADOTROPIN RELEASING HORMONE RECEPTOR ANTAGONISTS, METHOD FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
  申请人：SK CHEMICALS CO., LTD.

  公开号：US20150166558A1

  公开（公告）日：2015-06-18

  Disclosed are a gonadotropin releasing hormone receptor antagonist and a pharmaceutical composition including the same, which can be useful in preventing or treating a sex hormone-related disease such as endometriosis, amenorrhea, irregular menstruation, uterine myoma, uterine fibroids, polycystic ovarian disease, lupus erythematous, hypertrichosis, precocious puberty, short stature, acne, alopecia, gonadal steroid-dependent neoplasms, gonadotropin-producing pituitary adenoma, sleep apnea, irritable bowel syndrome, premenstrual syndrome, benign prostatic hyperplasia, contraception, and infertility, as well as Alzheimer disease.

  揭示了一种促性腺激素释放激素受体拮抗剂和包括该拮抗剂的药物组合物，可用于预防或治疗与性激素相关的疾病，如子宫内膜异位症、闭经、月经不调、子宫肌瘤、子宫纤维瘤、多囊卵巢综合征、红斑狼疮、多毛症、性早熟、身材矮小、痤疮、脱发、性腺类固醇依赖性肿瘤、促性腺激素产生垂体腺瘤、睡眠呼吸暂停、肠易激综合征、经前综合征、良性前列腺增生、避孕和不孕症，以及阿尔茨海默病。
• One-Pot Preparation of Enantiopure Fluorinated β-Amino Acid Precursors
  作者：Joshua H. Jones、Chandrakumar Appayee、Stacey E. Brenner-Moyer

  DOI：10.1002/ejoc.201402369

  日期：2014.8

  Specifically, carbon–nitrogen and carbon–fluorine bond-forming reactions were combined in an organocascade reaction to produce β-amino-α,α-difluoro carbonyl compounds containing alkyl substituents at the β-position. As such, this method is mechanistically distinct from, and complementary to, existing one-pot catalytic enantioselective methods for the preparation of fluorinated β-amino acid precursors

  手性 β-氟胺和 β,β-二氟胺是药用化合物中常见的亚结构。工业合成通常使用对映体纯的起始材料、手性助剂或对映体或非对映体混合物的拆分来以对映体纯的形式安装这些官能团。为了改善对这些亚结构的访问，我们最近开发了第一个催化对映选择性烯烃氨基卤化反应，该反应在单个烧瓶中从非手性烯醛起始材料生产手性 β-氟胺。本文介绍了将该方法扩展到制备 β-氨基-α,α-二氟羰基化合物的方法。具体来说，碳-氮和碳-氟键形成反应在有机级联反应中结合产生 β-氨基-α，在 β 位含有烷基取代基的 α-二氟羰基化合物。因此，该方法在机制上不同于现有的用于制备氟化 β-氨基酸前体的一锅催化对映选择性方法，并与之互补。