trans-(1R,2R)-2-(phenylseleno)-1-cyclohexanol | 35446-84-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-(1R,2R)-2-(phenylseleno)-1-cyclohexanol
• 英文别名: (1R,2R)-2-phenylseleno-1-cyclohexanol；2-phenylseleno-1-cyclohexanol；trans-2-(Phenylseleno)-cyclohexan-1-ol；rel-(1R,2R)-2-(Phenylseleno)cyclohexanol；(1R,2R)-2-phenylselanylcyclohexan-1-ol
• CAS: 35446-84-5
• 化学式: C₁₂H₁₆OSe
• 分子量: 255.218
• InChiKey: XNFLWQDTWVENJE-VXGBXAGGSA-N

物化性质

• 沸点：
  135-136 °C(Press: 1.2 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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-(1R,2R)-2-(phenylseleno)-1-cyclohexanol 、 次氯酸叔丁酯 以71%的产率得到
  参考文献：
  名称：

  DETTY M. R., J. ORG. CHEM., 1980, 45, NO 2, 274-279

  摘要：

  DOI：
• 作为产物：
  描述：

  三甲基苯基硒硅烷 、 二苯基硒亚砜 生成 trans-(1R,2R)-2-(phenylseleno)-1-cyclohexanol
  参考文献：
  名称：

  DETTY M. R., J. ORG. CHEM., 1979, 44, NO 25, 4528-4531

  摘要：

  DOI：

文献信息

• Synthesis of enantiomerically enriched β-hydroxy selenides by catalytic asymmetric ring opening of meso-epoxides with (phenylseleno)silanes
  作者：Marcello Tiecco、Lorenzo Testaferri、Francesca Marini、Silvia Sternativo、Francesca Del Verme、Claudio Santi、Luana Bagnoli、Andrea Temperini

  DOI：10.1016/j.tet.2008.01.126

  日期：2008.4

  The first example of the enantioselective ring opening of meso-epoxides by (phenylseleno)silanes using salen(Cr)complexes as catalyst is described. This desymmetrization reaction constitutes a simple and convenient approach to synthetically versatile optically active β-hydroxy selenides.

  的对映选择性开环的第一实施例的内消旋通过使用萨伦（Cr）的络合物作为催化剂进行说明（phenylseleno）硅烷-环氧化物。该去对称化反应构成了合成通用的光学活性β-羟基硒化物的简便方法。
• Catalytic Asymmetric Ring-Opening Reaction of<i>meso</i>-Epoxides with Aryl Selenols and Thiols Catalyzed by a Heterobimetallic Gallium-Titanium-Salen Complex
  作者：Jiangtao Sun、Minghua Yang、Fang Yuan、Xuefeng Jia、Xia Yang、Yi Pan、Chengjian Zhu

  DOI：10.1002/adsc.200800767

  日期：2009.4

  Abstractmagnified imageA chiral heterobimetallic Lewis acid complex has been developed as an efficient catalyst. The enantioselective desymmetrization of meso‐epoxides with aryl selenols and thiols catalyzed by the heterobimetallic complex has been optimized. The optically active β‐arylseleno alcohols and β‐hydroxy sulfides were obtained in good yields and high enantioselectivities (up to 97% ee and 92% ee, respectively). A strong synergistic effect between different Lewis acids was exhibited in the catalytic process.
• Enantioselective Ring-Opening Reaction of <i>m</i><i>eso-</i>Epoxides with ArSeH Catalyzed by Heterometallic Ti−Ga−Salen System
  作者：Minghua Yang、Chengjian Zhu、Fang Yuan、Yijun Huang、Yi Pan

  DOI：10.1021/ol0503034

  日期：2005.5.1

  [GRAPHICS]The first example of enantioselective ring-opening reaction of meso-epoxides with aryl selenols to give optically active beta-arylseleno alcohol in up to 97% ee was realized, using a chiral Ti-Ga-Salen heterometallic catalyst. A strong synergistic effect of different Lewis acids in the system was exhibited in the catalytic process.
• Biocatalytic reduction of a racemic selenocyclohexanone by Brazilian basidiomycetes
  作者：Leandro Piovan、Marina Capelari、Leandro H. Andrade、João V. Comasseto、André L.M. Porto

  DOI：10.1016/j.tetasy.2007.05.036

  日期：2007.7

  An efficient synthesis of the chiral cyclic secondary alcohols, trans-2-(phenylseleno)cyclohexanol la and cis-2-(phenylseleno)cyclohexanol la, was obtained by enzymatic reduction of 2-(phenylseleno)cyclohexanone I using whole fungal cells. Five strains of white-rot basidiomycetes were examined; Irpex lacteus CCB 196, Pycnoporus sanguineus CCB 196, Trametes rigida CCB 285, Trametes versicolor CCB 202 and Trichaptum byssogenum CCB 203. Cells of T rigida CCB 285 gave alcohols cis-(RS)-la and trans-(SS)-la in high enantiomeric excesses (ca. 99%). (c) 2007 Elsevier Ltd. All rights reserved.
• BACK T. G.; COLLINS S.; KERR R. G., J. ORG. CHEM., 1981, 46, NO 8, 1564-1570
  作者：BACK T. G.、 COLLINS S.、 KERR R. G.

  DOI：——

  日期：——