(1R*,2S*,5R*,6S*)-cyclooctane-1,2,5,6-tetrol | 215180-60-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R*,2S*,5R*,6S*)-cyclooctane-1,2,5,6-tetrol
• 英文别名: (1R,2S,5R,6S)-tetrahydroxycyclooctane；(1S,2R,5S,6R)-cyclooctane-1,2,5,6-tetrol
• CAS: 215180-60-2
• 化学式: C₈H₁₆O₄
• 分子量: 176.213
• InChiKey: GOFSZEWOPLAOPS-SOSBWXJGSA-N

物化性质

• 熔点：
  171-173 °C
• 沸点：
  324.3±42.0 °C(Predicted)
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1′-ferrocenediboronic acid 、 (1R*,2S*,5R*,6S*)-cyclooctane-1,2,5,6-tetrol 以 丙酮 为溶剂， 以69%的产率得到
  参考文献：
  名称：

  Synthesis of polymeric and macrocyclic Lewis acids: influence of backbone on degree of aggregation

  摘要：

  通过适当选择骨架框架，可一步合成多核路易斯酸，并对大环或聚合物阵列具有高选择性。

  DOI：

  10.1039/b709042k
• 作为产物：
  描述：

  1,5-cis,cis-cyclooctadiene 在 四氧化锇 、 N-甲基吲哚酮 作用下， 以 水 、 丙酮 为溶剂， 反应 7.0h， 以77%的产率得到(1R*,2S*,5R*,6S*)-cyclooctane-1,2,5,6-tetrol
  参考文献：
  名称：

  Dihydroxylation of Polyenes Using Narasaka's Modification of the Upjohn Procedure

  摘要：

  Dihydroxylation of a variety of commercially available polyenes has been investigated using phenylboronic acid, N-methylmorpholine N-oxide (NMO), and osmium tetroxide in anhydrous solvent. The diastereoselectivity of multiple oxidation steps is in some cases affected by the in situ protection of the intermediate ene-diols as phenyboronic esters, affording polyols not available from the standard Upjohn dihydroxylation procedure. A convenient oxidative deprotection of the phenylboronic esters is also described.

  DOI：

  10.1021/jo980850l

文献信息

• ON THE STEREOSELECTIVITY IN BISDIHYDROXYLATION OF 1,5-CYCLOOCTADIENE WITH OSMIUM TETROXIDE
  作者：Kentaro Kawazoe、Yoshio Furusho、Saburo Nakanishi、Toshikazu Takata

  DOI：10.1081/scc-100104460

  日期：2001.1.1

  In the bisdihydroxylation of 1,5-cyclooctadiene with OsO4, use of a stoichiometric amount of OsO4 yielded a 1: 1 mixture of syn- and anti-isomers, while use of a catalytic amount of OsO4 gave only syn-(1R*,2S*,5R*,6S*)-cyclooctane-1,2,5,6-tetrol. This syn-selectivity was attributed to the favorable formation of an intramolecular osmium(VI) bisglycolate ester in the catalytic reaction.
• ORGANOMETALLIC SENSOR DEVICE
  申请人：Aldridge Simon

  公开号：US20100285602A1

  公开（公告）日：2010-11-11

  The present invention relates to detectors for detecting fluorine-containing compounds and/or cyanide containing compounds, including hydrogen fluoride (HF) or HCN gas, hydrofluoric acid in solution, selected chemical warfare agents, selected industrial chemicals which may be hydrolysed to release HF or HCN gas, compounds containing a cyanide group, and compounds that can release HF or HCN. The detectors comprise i) an organometallic component containing at least one bis-substituted boryl group of the formula —B(R B )(R B +) wherein each R B and each R B′ is independently selected from H, halogen, C 1-6 alkyl, OR 6 , N(R 6 )(R 7 ), SR 6 , C 3-20 aryl or heteroaryl, and C 3-20 cycloalkyl or heterocycloalkyl groups, each of which may be optionally substituted, ii) a Lewis base component, and iii) a solid matrix component. The invention also relates to novel organometallic compounds containing at least one bis-substituted boryl group and their use in detectors for fluorine containing compounds and/or cyanide containing compounds.
• US9023652B2
  申请人：——

  公开号：US9023652B2

  公开（公告）日：2015-05-05
• [EN] FERROCENYL BORONIC ACID BASED SENSOR FOR FLUORIDE AND CYANIDE<br/>[FR] CAPTEUR DE FLUOR ET DE CYANURE A BASE D'ACIDE FERROCENYL BORONIQUE
  申请人：UNIV CARDIFF

  公开号：WO2008078092A1

  公开（公告）日：2008-07-03

  [EN] The present invention relates to detectors for detecting fluorine containing compounds and/or cyanide containing compounds, including hydrogen fluoride (HF) or HCN gas, hydrofluoric acid in solution, selected chemical warfare agents, selected industrial chemicals which may be hydrolysed to release HF or HCN gas, compounds containing a cyanide group, and compounds that can release HF or HCN. The detectors comprise i) an organometallic component containing at least one bis-substituted boryl group of the formula B(R^B)(R^B'), wherein each R^B and each R^B' is independently selected from H, halogen, C_1-6 alkyl, OR⁶, N(R⁶)(R⁷), SR⁶, C_3-20 aryl or heteroaryl, and C_3-20 cycloalkyl or heterocycloalkyl groups, each of which may be optionally substituted, ii) a Lewis base component, and iii) a solid matrix component. The invention also relates to novel organometallic compounds containing at least one bis-substituted boryl group and their use in detectors for fluorine containing compounds and/or cyanide containing compounds.
  [FR] L'invention concerne des détecteurs servant à détecter des composés contenant du fluor et/ou des composés contenant du cyanure, notamment du gaz de fluorure d'hydrogène (HF) ou de HCN, de l'acide fluorhydrique en solution, des agents de guerre chimique déterminés, des substances chimiques industrielles déterminées pouvant être hydrolysées pour libérer un gaz HF ou HCN, des composés contenant un groupe cyanure et des composés aptes à libérer HF ou HCN. Les détecteurs selon l'invention comprennent : i) un composant organométallique contenant au moins un groupe boryle bis-substitué de formule B(R^B)(R^B'), dans laquelle chaque R^B et chaque R^B' est sélectionné indépendamment parmi H, halogène, alkyle C_1-6, OR⁶, N(R⁶)(R⁷), SR⁶, aryle ou hétéroaryle C_3-20 et des groupes cycloalkyle ou hétérocycloalkyle C_3-20, chacun pouvant être facultativement substitué; ii) un composant base de Lewis; et iii) un composant matriciel solide. L'invention concerne également de nouveaux composés organométalliques contenant au moins un groupe boryle bis-substitué, ainsi que leur utilisation dans des détecteurs de composés contenant du fluor et/ou de composés contenant du cyanure.