(+/-)-trans-2-chlorocycloheptanol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-trans-2-chlorocycloheptanol
• 英文别名: (+/-)-2-chlorocycloheptanol；(+/-)-2t-chloro-cycloheptan-r-ol；(+/-)-2t-Chlor-cycloheptan-r-ol；(+/-)-trans-2-Chlor-cycloheptanol-(1)；(1R,2R)-2-chlorocycloheptan-1-ol
• 化学式: C₇H₁₃ClO
• 分子量: 148.633
• InChiKey: ZVHKXELYDFJYOO-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+/-)-trans-2-chlorocycloheptanol 在 sodium carbonate 作用下， 生成 1,2-环氧基环庚烷
  参考文献：
  名称：

  Epoxidation with the H2O2/vilsmeier reagent system

  摘要：

  DOI：

  10.1016/s0040-4039(00)87212-3
• 作为产物：
  描述：

  (1R,2R)-1,2-环庚烷二醇 在 盐酸 作用下， 生成 (+/-)-trans-2-chlorocycloheptanol
  参考文献：
  名称：

  Mousseron; Winternitz; Combes, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1946, vol. 222, p. 1503

  摘要：

  DOI：

文献信息

• Enantioselective epoxide ring opening catalyzed by bis(tetrahydroisoquinoline) N,N′-dioxides
  作者：Aneta Kadlčíková、Klára Vlašaná、Martin Kotora

  DOI：10.1135/cccc2011024

  日期：——

  Four bis(tetrahydroisoquinoline) N,N′-dioxides were used as catalysts for the epoxide ring opening with tetrachlorosilane under various conditions. A strong solvent effect on asymmetric induction was observed for each of the used catalysts. The highest achieved asymmetric induction for the opening of meso-stilbene oxide was 69% ee. Regarding the cycloalkene oxides, 56% ee was obtained in the reaction with cyclooctene oxide.

  四种双(四氢异喹啉)N,N′-二氧化物被用作催化剂，用于在不同条件下与四氯硅烷开环环氧化物。观察到溶剂对对称诱导的影响。对于开环meso-苯乙烯环氧化物，最高达到的对称诱导率为69% ee。对于环烯氧化物，反应与环辛烯氧化物得到了56% ee。
• Enantioselective Ring Opening of<i>meso</i>-Epoxides with Silicon Tetrachloride Catalyzed by Pyridine<i>N</i>-Oxides Fused with the Bicyclo[3.3.1]nonane Framework
  作者：Algirdas Neniškis、Sigitas Stončius

  DOI：10.1002/ejoc.201500762

  日期：2015.10

  chiral Lewis basic organocatalysts that contain pyridine N-oxide moieties fused with the bicyclo[3.3.1]nonane framework is reported. The obtained pyridine N-oxides were employed as catalysts in the enantioselective ring opening of meso-epoxides with silicon tetrachloride. Derivative 1b endowed with two 2,4-diaryl-substituted pyridine N-oxide moieties proved to be a particularly effective catalyst for desymmetrization

  报道了新的手性路易斯碱性有机催化剂的合成，该催化剂含有与双环 [3.3.1] 壬烷骨架稠合的吡啶 N-氧化物部分。所得吡啶N-氧化物用作中间环氧化物与四氯化硅对映选择性开环的催化剂。具有两个 2,4-二芳基取代的吡啶 N-氧化物部分的衍生物 1b 被证明是一种特别有效的催化剂，可用于降冰片烯氧化物 16i 的去对称化，以提供前所未有的 96% ee 的 Wagner-Meerwein 重排产物 20i。双功能同源物 3 带有 4-芳基取代基，与脂环族环氧化物底物表现出中等至高水平的不对称诱导（47-88% ee）。
• New chiral organophosphorus derivatizing agent for the determination of enantiomeric composition of chloro- and bromohydrins by 31P NMR spectroscopy
  作者：Sébastien Reymond、Jean Michel Brunel、Gérard Buono

  DOI：10.1016/s0957-4166(00)00062-8

  日期：2000.4

  The synthesis of a new chiral organophosphorus derivatizing agent prepared from (S)-2-anilinomethylpyrrolidine 1 and its successful use in the determination of enantiomeric composition of various halohydrins by 31P NMR spectroscopy is described.

  描述了由（S）-2-苯胺基甲基吡咯烷1制备的新型手性有机磷衍生剂的合成及其在31 P NMR光谱法成功确定各种卤代醇的对映体组成中的应用。
• Dichlorotin oxide-catalyzed new direct functionalization of olefins: synthesis of trans β-azidohydrins and 1,2-diols
  作者：Isao Sakurada、Shingo Yamasaki、Motomu Kanai、Masakatsu Shibasaki

  DOI：10.1016/s0040-4039(00)00176-3

  日期：2000.4

  We have succeeded in developing direct syntheses of trans β-azidohydrins and trans 1,2-diol derivatives from olefins catalyzed by dichlorotin oxide. The regioselectivity of these reactions with tri-substituted olefins is high (10:1 in the synthesis of 1,2-diol derivatives) to excellent (>99:1 in the synthesis of azidohydrins). It has been found that these reactions do not proceed via epoxides.

  我们已经成功地开发了由二氯氧化锡催化的烯烃直接合成反式β-叠氮醇和反式1,2-二醇衍生物。这些与三取代的烯烃的反应的区域选择性高（在合成1,2-二醇衍生物中为10：1）至优异的（在叠氮醇中合成为> 99：1）。已经发现这些反应不会通过环氧化物进行。
• Ionic Liquid as Reagent. A Green Procedure for the Regioselective Conversion of Epoxides to <i>V</i><i>icinal</i>-Halohydrins Using [AcMIm]X under Catalyst- and Solvent-Free Conditions
  作者：Brindaban C. Ranu、Subhash Banerjee

  DOI：10.1021/jo0500885

  日期：2005.5.1

  A variety of structurally diverse epoxides undergo facile cleavages by ionic liquid, [AcMIm]X without any catalyst and solvent to produce the corresponding vicinal halohydrins in high yields. The cleavages are considerably fast and highly regioselective.