tert-butyl (1R,3S,5S)-6-oxabicyclo[3.1.0]hexan-3-ylcarbamate | 250659-32-6

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: tert-butyl (1R,3S,5S)-6-oxabicyclo[3.1.0]hexan-3-ylcarbamate
• 英文别名: racemic tert-butyl ((1R,3S,5S)-6-oxabicyclo[3.1.0]hexan-3-yl)carbamate；anti-tert-butyl (6-oxabicyclo[3.1.0]hex-3-yl)carbamate；N-Boc (1R,3s,5S)-6-oxabicyclo[3.1.0]hexan-3-amine；anti tert-butyl(6-oxa-bicyclo[3.1.0]hex-3-yl)carbamate
• CAS: 250659-32-6
• 化学式: C₁₀H₁₇NO₃
• 分子量: 199.25
• InChiKey: GUVWHGMHXIFPGI-WHUPJOBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.44
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  50.86
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (1R,3S,5S)-6-oxabicyclo[3.1.0]hexan-3-ylcarbamate 在 1,5-二氮杂双环[4.3.0]壬-5-烯 、 四丁基氯化铵 、 一水合肼 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 39.33h， 生成 14-O-{[(1RS,2RS,4RS)-4-tert-butoxycarbonylamino-2-hydroxycyclopentylsulfanyl]acetyl}mutilin
  参考文献：
  名称：

  Pleuromutilin derivatives for use in the treatment of diseases mediated by microbes

  摘要：

  从N-未取代或N-烷基化或N-酰化的14-O-[(氨基(C0-4)烷基-羟基-环烷基或双环烷基硫醚基)-乙酰基]-螺旋霉素中选择的化合物，其为14-O-[(氨基(C0-4)烷基-羟基-环丁基硫醚基)-乙酰基]-螺旋霉素，14-O-[(氨基(C0-4)烷基-羟基-环戊基硫醚基)-乙酰基]-螺旋霉素，14-O-[(氨基(C0-4)烷基-羟基-环庚基硫醚基)-乙酰基]-螺旋霉素，14-O-[(氨基(C0-4)烷基-羟基-环辛基硫醚基)-乙酰基]-螺旋霉素，或14-O-[(氨基(C0-4)烷基-羟基-双环烷基硫醚基)-乙酰基]-螺旋霉素，可选地以盐和/或溶剂的形式存在，包括这些化合物的药物组合物以及它们作为药物的用途，例如用于治疗微生物感染和痤疮的治疗，可选地与其他药用活性剂联合使用。

  公开号：

  EP2433926A1
• 作为产物：
  描述：

  环戊-3-烯-1-醇甲磺酸盐 在 盐酸 、 4-二甲氨基吡啶 、 Oxone 、 sodium azide 、 1,1,1-三氟丙酮 、 水 、 碳酸氢钠 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 52.0h， 生成 tert-butyl (1R,3S,5S)-6-oxabicyclo[3.1.0]hexan-3-ylcarbamate
  参考文献：
  名称：

  4-氨基环戊-2-烯-1-醇的新途径：4-氨基取代的环戊烯氧化物的合成和对映选择性重排

  摘要：

  描述了用于碳环核苷类似物合成的4-氨基环戊-2-en-1-醇（90％ee）的不对称合成的新途径。该方法涉及立体选择性制备顺式4-氨基取代的环戊烯氧化物和随后手性碱介导的重排成相应的烯丙基醇。给出了4-氨基取代的环戊烯环氧化的合成和立体选择性的全部细节。

  DOI：

  10.1016/s0040-4020(00)00911-x

文献信息

• [EN] PLEUROMUTILIN DERIVATIVES FOR USE IN THE TREATMENT OF DISEASES MEDIATED BY MICROBES<br/>[FR] DÉRIVÉS DE PLEUROMUTILLINE DESTINÉS À ÊTRE UTILISÉS DANS LE TRAITEMENT DE MALADIES MÉDIÉES PAR DES MICROBES
  申请人：NABRIVA THERAPEUTICS AG

  公开号：WO2012031307A1

  公开（公告）日：2012-03-15

  Compounds selected from the group of N-unsubstituted or N-alkylated or N-acylated 14-O-[(amino(C0-4)alkyl-hydroxy-cycloalkyl- or bicycloalkylsulfanyl)-acetyl]-mutilins which are 14-O-[(amino(C0-4)alkyl-hydroxy-cyclobutylsulfanyl)-acetyl]-mutilins, 14-O-[(amino(C0-4)alkyl-hydroxy-cyclopentylsulfanyl)-acetyl]-mutilins, 14-O-[(amino(C0-4)alkyl-hydroxy- cycloheptylsulfanyl)-acetyl]-mutilins, 14-O-[(amino(C0-4)alkyl-hydroxy-cyclooctylsulfanyl)- acetyl]-mutilins, or 14-O-[(amino(C0-4)alkyl-hydroxy-bicycloalkylsulfanyl)-acetyl]-mutilins, optionally in the form of a salt and/or a solvate, a pharmaceutical compositions comprising such compounds and their use as pharmaceuticals, e.g. for the treatment of microbial infections and for the treatment of acne, optionally in combination with other pharmaceutically active agents.

  从N-未取代或N-烷基化或N-酰化的14-O-[(氨基(C0-4)烷基-羟基-环烷基或双环烷基硫基)-乙酰基]-麦角新霉素中选择的化合物，这些化合物是14-O-[(氨基(C0-4)烷基-羟基-环丁基硫基)-乙酰基]-麦角新霉素、14-O-[(氨基(C0-4)烷基-羟基-环戊基硫基)-乙酰基]-麦角新霉素、14-O-[(氨基(C0-4)烷基-羟基-环庚基硫基)-乙酰基]-麦角新霉素、14-O-[(氨基(C0-4)烷基-羟基-环辛基硫基)-乙酰基]-麦角新霉素，或14-O-[(氨基(C0-4)烷基-羟基-双环烷基硫基)-乙酰基]-麦角新霉素，可选地以盐和/或溶剂的形式存在，包括这些化合物的药物组合物以及它们作为药物的用途，例如用于治疗微生物感染和治疗痤疮，可选地与其他药用活性剂结合使用。
• On the possibility of carbamate-directed hydroboration. An approach to the asymmetric synthesis of 1-aminocyclopentane-1,3-dicarboxylic acid
  作者：David M Hodgson、Alison J Thompson、Sjoerd Wadman、Clare J Keats

  DOI：10.1016/s0040-4020(99)00596-7

  日期：1999.8

  Hydroboration (using BH3) of 1-substituted 3-cyclopentenes 3, 9 and 17 and an enantioselective synthesis of the excitatory amino acid 1-aminocyclopentane-1,3-dicarboxylic acid via asymmetric hydroboration [90% de, 45% ee using (+)-IpeBH2] of cyclopentene 17 are described.

  硼氢化反应（使用BH 3）的1-取代-3-环戊烯3,9和17和兴奋性氨基酸1-氨基环戊烷-1,3-二羧酸的对映选择性合成通过不对称硼氢化[90％德，45％ee的使用（描述了环戊烯17的+）-IpeBH 2 ] 。
• WO2020150113A5
  申请人：——

  公开号：WO2020150113A5

  公开（公告）日：2022-09-05
• Synthesis and enantioselective rearrangement of 4-amino-substituted cyclopentene oxides
  作者：Peter O'Brien、Timothy D. Towers、Matthias Voith

  DOI：10.1016/s0040-4039(98)01821-8

  日期：1998.10

  Several N-mono- and diprotected alkenes have been prepared and the, stereoselectivity of their epoxidation has been investigated: N-monoprotected alkenes give cis epoxides preferentially (due to hydrogen bonding directed epoxidations) whereas N-diprotected alkenes produce trans epoxides exclusively (due to steric effects). Chiral lithium amide base-mediated rearrangement of a cis-monoprotected epoxide generated the corresponding amino-cyclopentenol in good yield and with an enantiomeric excess of 60%. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Minimal Pharmacophoric Elements and Fragment Hopping, an Approach Directed at Molecular Diversity and Isozyme Selectivity. Design of Selective Neuronal Nitric Oxide Synthase Inhibitors
  作者：Haitao Ji、Benjamin Z. Stanton、Jotaro Igarashi、Huiying Li、Pavel Martásek、Linda J. Roman、Thomas L. Poulos、Richard B. Silverman

  DOI：10.1021/ja0772041

  日期：2008.3.1

  Fragment hopping, a new fragment-based approach for de novo inhibitor design focusing on ligand diversity and isozyme selectivity, is described. The core of this approach is the derivation of the minimal pharmacophoric element for each pharmacophore. Sites for both ligand binding and isozyme selectivity are considered in deriving the minimal pharmacophoric elements. Five general-purpose libraries are established: the basic fragment library, the bioisostere library, the rules for metabolic stability, the toxicophore library, and the side chain library. These libraries are employed to generate focused fragment libraries to match the minimal pharmacophoric elements for each pharmacophore and then to link the fragment to the desired molecule. This method was successfully applied to neuronal nitric oxide synthase (nNOS), which is implicated in stroke and neurodegenerative diseases. Starting with the nitroarginine-containing dipeptide inhibitors we developed previously, a small organic molecule with a totally different chemical structure was designed, which showed nanomolar nNOS inhibitory potency and more than 1000-fold nNOS selectivity. The crystallographic analysis confirms that the small organic molecule with a constrained conformation can exactly mimic the mode of action of the dipeptide nNOS inhibitors. Therefore, a new peptidomimetic strategy, referred to as fragment hopping, which creates small organic molecules that mimic the biological function of peptides by a pharmacophore-driven strategy for fragment-based de novo design, has been established as a new type of fragment-based inhibitor design. As an open system, the newly established approach efficiently incorporates the concept of early "ADME/Tox" considerations and provides a basic platform for medicinal Chemistry-driven efforts.