(3R,4S,5S,6S)-1-bromo-5,6-O-isopropylidene-1-cyclohexene-3,4,5,6-tetrol | 192448-70-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,5S,6S)-1-bromo-5,6-O-isopropylidene-1-cyclohexene-3,4,5,6-tetrol
• 英文别名: (3aS,4S,5R,7aS)-7-bromo-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxole-4,5-diol
• CAS: 192448-70-7
• 化学式: C₉H₁₃BrO₄
• 分子量: 265.104
• InChiKey: UGCLVZMHFRQWFL-CWKFCGSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S,6S)-1-bromo-5,6-O-isopropylidene-1-cyclohexene-3,4,5,6-tetrol 在 四氧化锇 、 N-甲基吲哚酮 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲醇 、 水 、 丙酮 、 叔丁醇 、 苯 为溶剂， 反应 90.0h， 生成 (3aS,4S,5R,6S,7S,7aR)-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxole-4,5,6,7-tetrol
  参考文献：
  名称：

  A short, stereoselective synthesis of neo-inositol

  摘要：

  A practical synthesis of neo-inositol is described in which the target is prepared on a multigram scale in six operations from bromobenzene. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00289-x
• 作为产物：
  描述：

  (1S-顺式)-3-溴-3,5-环己二烯-1,2-二醇 在 N-碘代丁二酰亚胺 、 水 、 对甲苯磺酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 丙酮 为溶剂， 反应 12.0h， 生成 (3R,4S,5S,6S)-1-bromo-5,6-O-isopropylidene-1-cyclohexene-3,4,5,6-tetrol
  参考文献：
  名称：

  从手性环己二烯二醇支架合成 (-)-Conduritol C 和类似物的一般方法

  摘要：

  描述了一种利用单取代苯的对映选择性生物催化过程合成 conduritol C 类似物的有效和简便的通用方法。目标分子 (-)-conduritol C、(-)-bromo-conduritol C 和 (-)-methyl-conduritol C 的绝对立体化学模式是通过化学酶法实现的。源自芳烃生物转化的同手性环己二烯-顺-1,2-二醇的立体化学和非分离的乙烯基环氧化物衍生物的对映选择性开环允许在目标分子上建立带有羟基的碳的绝对构型. 所有三种球状糖醇和两种中间体均已结晶，并通过 X 射线衍射证实了它们的结构。三种结构糖醇和中间体是同构的。我们方法的多功能性值得注意，可扩展从甲苯双加氧酶 (TDO) 单取代芳烃底物开始制备 conduritol C 类似物。

  DOI：

  10.3390/molecules23071653

文献信息

• Use of Electrochemical Methods as an Alternative to Tin Reagents for the Reduction of Vinyl Halides in Inositol Synthons
  作者：Tomas Hudlicky、Christopher D. Claeboe、Larry E. Brammer、Lukasz Koroniak、Gabor Butora、Ion Ghiviriga

  DOI：10.1021/jo990382v

  日期：1999.6.1

  previously used in inositol syntheses were subjected to electrochemical reduction. The unreactivity of allylic alcohols or allylic ethers at the applied potentials allowed the selective reduction of vinyl halides to olefins. Electrochemical methods provide for selective reduction of vinyl iodides over vinyl bromides, with better yields than analogous tin methodology. Cinnamyl ethers were reductively

  将先前用于肌醇合成的几种乙烯基卤化物进行电化学还原。烯丙基醇或烯丙基醚在所施加的电势下的不反应性使得卤化乙烯选择性地还原为烯烃。电化学方法提供了比乙烯基溴选择性还原乙烯基碘的方法，其收率高于类似的锡方法。在烷基烯丙基醚存在下，肉桂醚在-3.2 V（vs Ag / AgNO（3））上进行还原裂解，以提供选择性脱保护。在乙烯基环氧乙烷或乙烯基氮丙啶的存在下，卤化乙烯的电化学还原伴随着应变环的溶剂分解。报告了产率和条件，并将其与标准锡诱导的脱卤方法进行了比较。
• Chemoenzymatic synthesis of enantiopure α-substituted cyclohexanones from aromatic compounds
  作者：Germán Fonseca、Gustavo A. Seoane

  DOI：10.1016/j.tetasy.2005.02.012

  日期：2005.4

  A series of chiral alpha-substituted cyclohexanones have been synthesized from chemoenzymatically produced chlorocyclo-hexadienediol. These highly functionalized ketones can be used in the total synthesis of diverse natural products, such as bengamides. A study of the reactivity of alpha-chlorooxiranes, common intermediates in the synthetic scheme, showed that under nucleophilic opening conditions an intermediate chloroketone may or may not form, depending on the nature of the nucleophiles present in the reaction medium. The stereochemical outcome of this reaction is presented. (c) 2005 Elsevier Ltd. All rights reserved.
• Chemoenzymatic synthesis of deoxyfluoroinositols: 5-deoxy-5-fluoro-myo-inositol and 3-deoxy-3-fluoro-L-chiro-inositol
  作者：Ba V. Nguyen、Chentao York、Tomas Hudlicky

  DOI：10.1016/s0040-4020(97)90392-6

  日期：1997.6
• Stille reaction over cis-halocyclohexadienediol derivatives
  作者：Viviana Heguaburu、Marcus Mandolesi Sá、Valeria Schapiro、Enrique Pandolfi

  DOI：10.1016/j.tetlet.2008.09.049

  日期：2008.11

  Stille reaction was performed with several halo cis-diol derivatives by reaction with allyltributyltin in the presence of a palladium Catalyst forming allyl cis-clihydrodiol derivatives. These couplings were conducted with conventional heating as well as with microwave irradiation. Allylbenzene cis-dihydrodiol was obtained with excellent yield using mild conventional hearing. However, if the diol moiety is protected with the isopropylidene group, the expected product is obtained Only Under microwave irradiation. The unusual reactivity observed for the polyoxygenated derivatives suggests assistance of the free hydroxyls in the catalytic cycle. (C) 2008 Elsevier Ltd. All rights reserved.
• General Method for the Synthesis of (−)-Conduritol C and Analogs from Chiral Cyclohexadienediol Scaffolds
  作者：Gaurao Tibhe、Mario Macías、Valeria Schapiro、Leopoldo Suescun、Enrique Pandolfi

  DOI：10.3390/molecules23071653

  日期：——

  permitted the absolute configuration of the carbon bearing the hydroxyl groups at the target molecules to be established. All three conduritols and two intermediates were crystallized, and their structures were confirmed by X-ray diffraction. The three conduritols and intermediates were isostructural. The versatility of our methodology is noteworthy to expand the preparation of conduritol C analogs starting

  描述了一种利用单取代苯的对映选择性生物催化过程合成 conduritol C 类似物的有效和简便的通用方法。目标分子 (-)-conduritol C、(-)-bromo-conduritol C 和 (-)-methyl-conduritol C 的绝对立体化学模式是通过化学酶法实现的。源自芳烃生物转化的同手性环己二烯-顺-1,2-二醇的立体化学和非分离的乙烯基环氧化物衍生物的对映选择性开环允许在目标分子上建立带有羟基的碳的绝对构型. 所有三种球状糖醇和两种中间体均已结晶，并通过 X 射线衍射证实了它们的结构。三种结构糖醇和中间体是同构的。我们方法的多功能性值得注意，可扩展从甲苯双加氧酶 (TDO) 单取代芳烃底物开始制备 conduritol C 类似物。