trans-2-<(2-hydroxyethyl)thio>cyclohexanol | 71989-47-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-2-<(2-hydroxyethyl)thio>cyclohexanol
• 英文别名: trans-2-hydroxycyclohexyl 2-hydroxyethyl sulfide；trans-2-hydroxycyclohexyl-2-hydroxyethyl sulfide；trans-2-(2-hydroxyethylthio)cyclohexanol；2-(2-hydroxyethylthio)cyclohexanol；(+/-)-trans-2-(2-hydroxy-ethylsulfanyl)-cyclohexanol；(+/-)-trans-2-(2-Hydroxy-aethylmercapto)-cyclohexanol；rel-(1R,2R)-2-[(2-Hydroxyethyl)thio]cyclohexanol；(1R,2R)-2-(2-hydroxyethylsulfanyl)cyclohexan-1-ol
• CAS: 71989-47-4
• 化学式: C₈H₁₆O₂S
• 分子量: 176.28
• InChiKey: AVPZUKGXTUBAQQ-HTQZYQBOSA-N

物化性质

• 沸点：
  340.8±32.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  65.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-2-<(2-hydroxyethyl)thio>cyclohexanol 在 diethoxyltriphenylphosphorane 作用下， 以 二氯甲烷 为溶剂， 生成 trans-1,4-oxathiadecalin
  参考文献：
  名称：

  Diethoxytriphenylphosphorane: a mild, regioselective cyclodehydrating reagent for conversion of diols to cyclic ethers: stereochemistry, synthetic utility, and scope

  摘要：

  DOI：

  10.1021/ja00304a030
• 作为产物：
  描述：

  氧化环己烯 、 2-巯基乙醇 以 乙醇 为溶剂， 以17.8 g的产率得到trans-2-<(2-hydroxyethyl)thio>cyclohexanol
  参考文献：
  名称：

  Carbon-13 nuclear magnetic resonance spectra of trans-1-thiadecalin, trans-1,4-thiadecalin, trans-1,4-oxathiadecalin, and the corresponding sulfoxides and sulfones

  摘要：

  DOI：

  10.1021/jo01289a043

文献信息

• Experimental Evidence for Negative Hyperconjugation as a Component of the Polar Effect:  Variation of the Ease of α-Sulfonyl Carbanion Formation with the Orientation of a β-Alkoxy Substituent
  作者：James F. King、Rajendra Rathore、Zhenrong Guo、Manqing Li、Nicholas C. Payne

  DOI：10.1021/ja001320l

  日期：2000.10.1

  the incipient carbanion into the # C-O / orbital. This effect is largest with torsion angles of 0 and 180ϒ and at these torsion angles constitutes the major source of stabilization of the incipient carbanion by the ! -alkoxy group. The present observation of a torsion-angle-dependent substituent effect may be combined with the known adherence of the specific rate of R-sulfonyl carbanion formation to

  我们报告了强烈依赖几何的取代基效应的证据。R-氢的 HD 交换速率常数 (kexch)OR，在一组 19 ! - 已知的、固定的（或强烈优选的）H-CR-C 的烷氧基砜！- 或已测量扭转角。还测量了缺少烷氧基的相应模型化合物 (kexch) 模型的那些，从而提供比率 kN ) (kexch)OR/(kexch) 模型；如此获得的 kN 值范围超过 4 个数量级。我们表明，当考虑到空间和其他影响时，我们的观察结果与 log kN ) a + b cos 2 " (其中 a ) 1.70 ( 0.17 和 b ) 2.62 ( 0.20) 形式的方程一致。它是进一步表明，观察到的速率常数比与仅由感应效应和场效应组成的取代效应不一致，并且它们与第三种效应的额外存在完全一致，即负超共轭或广义异头效应，特别是初始碳负离子的部分负电荷向#CO/轨道的扭转角依赖性捐赠。这种效应在扭转角为 0 和 180
• 660. Dithiols. Part XI. The reactions of epoxides with hydroxy- and poly-thiols
  作者：L. N. Owen、Peter N. Smith

  DOI：10.1039/jr9510002973

  日期：——
• Efficient synthesis of β, β’-dihydroxy sulfides by ring opening of epoxides with mercaptoethanol catalyzed under solvent-free conditions
  作者：Moufida Romdhani-Younes、Mohamed Moncef Chaabouni

  DOI：10.1080/17415993.2012.662685

  日期：2012.4.1

  A simple and highly efficient synthesis of beta, beta'-dihydroxy sulfides has been achieved by ring opening of epoxides with mercaptoethanol using catalytic amount of benzyltrimethylammonium hydroxide (Triton B) under solvent-free conditions. Excellent regioselectivity was found for aliphatic unsymmetrical epoxides, with nucleophilic attack at the less-hindered carbon atom of the epoxide. However, this regioselectivitywas not observed for styrene oxide and a mixture of two isomers was obtained. This process was also regio- and chemo-selective as illustrated using epichlorohydrin with two epoxide ring positions and mercaptoethanol with two functional groups (SH and OH).[GRAPHICS].1a-e 2ae(1)(alpha) 2e(2)(beta)R = CH3(a) ; C2H3(b) ; CICH2(c) ; PhOCH2(d) ; ph(e).
• Cyclodehydration and selective chlorination of trans-2-hydroxycyclohexyl 2-hydroxyethyl sulfide with triphenylphosphine and tetrachloromethane
  作者：Carey N. Barry、Steven J. Baumrucker、Robert C. Andrews、Slayton A. Evans

  DOI：10.1021/jo00141a036

  日期：1982.9
• Samoshin, V. V.; Vereshchagina, Ya. A.; Konoplyanko, N. V., Russian Journal of Organic Chemistry, 1993, vol. 29, # 1.2, p. 183 - 184
  作者：Samoshin, V. V.、Vereshchagina, Ya. A.、Konoplyanko, N. V.、Lutsenko, A. I.、Zefirov, N. S.

  DOI：——

  日期：——