(+/-)-(S,S)-2,3-dihydro-2-(phenylseleno)-1H-inden-1-ol | 918442-98-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (+/-)-(S,S)-2,3-dihydro-2-(phenylseleno)-1H-inden-1-ol
• 英文别名: anti-2-(phenylselanyl)-2,3-dihydro-1H-inden-1-ol；(+/-)-trans-2-phenylselenoindanol；(1S,2S)-2-phenylselanyl-2,3-dihydro-1H-inden-1-ol
• CAS: 918442-98-5
• 化学式: C₁₅H₁₄OSe
• 分子量: 289.236
• InChiKey: CKKRYKLAQXSMSH-GJZGRUSLSA-N

物化性质

• 沸点：
  426.4±45.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (+/-)-(S,S)-2,3-dihydro-2-(phenylseleno)-1H-inden-1-ol 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 生成 R-(-)-1-茚酚
  参考文献：
  名称：

  Lipase-catalyzed resolution of β-hydroxy selenides

  摘要：

  Eleven beta-hydroxy selenides were kinetically resolved using an immobilized lipase (Amano PS-C II) in toluene in the presence of vinyl acetate at 30 degrees C. This approach provided, in several cases, both enantiomers in high enantiomeric excess. The role of the size of substituents and the behaviour of cyclic beta-hydroxy selenides is also discussed. Enantiopure beta-hydroxy selenides are useful building blocks. As an application of this chemistry, enantiopure (1S,2R)-indene oxide was obtained in one step from the proper enantiopure beta-hydroxy selenide. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.10.010
• 作为产物：
  描述：

  苯基氯化硒 在 PS-C II Amano lipase 、 水 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 48.0h， 生成 (+/-)-(S,S)-2,3-dihydro-2-(phenylseleno)-1H-inden-1-ol
  参考文献：
  名称：

  Lipase-catalyzed resolution of β-hydroxy selenides

  摘要：

  Eleven beta-hydroxy selenides were kinetically resolved using an immobilized lipase (Amano PS-C II) in toluene in the presence of vinyl acetate at 30 degrees C. This approach provided, in several cases, both enantiomers in high enantiomeric excess. The role of the size of substituents and the behaviour of cyclic beta-hydroxy selenides is also discussed. Enantiopure beta-hydroxy selenides are useful building blocks. As an application of this chemistry, enantiopure (1S,2R)-indene oxide was obtained in one step from the proper enantiopure beta-hydroxy selenide. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.10.010

文献信息

• Iodosobenzene-Mediated Three-Component Selenofunctionalization of Olefins
  作者：Zhi-Peng Liang、Wei Yi、Peng-Fei Wang、Gong-Qing Liu、Yong Ling

  DOI：10.1021/acs.joc.1c00257

  日期：2021.4.2

  A three-component reaction of olefin, diselenide and water, alcohols, phenol, carboxylic acid, or amine by a commercially available hypervalent iodine(III) reagent, PhIO, was developed. This method provides access to a wide range of vicinally functionalized selenoderivatives under ambient conditions with mostly excellent yields and high diastereoselectivity. The developed reaction displays high levels

  通过市售的高价碘（III）试剂PhIO，开发了烯烃，二硒化物与水，醇，酚，羧酸或胺的三组分反应。这种方法可以在环境条件下获得大多数具有毒理学功能的亚硒代衍生物，并且产率极高，非对映选择性很高。所开发的反应显示出高水平的官能团相容性，并且适合于苯乙烯官能化生物分子的后期官能化。还介绍了反应机理的初步研究。
• Aerobic Copper(II)-catalyzed synthesis of β-hydroxysulfides and selenides from alkenes with disulfides and diselenides
  作者：Nobukazu Taniguchi

  DOI：10.1016/j.tet.2022.132689

  日期：2022.3

  A copper-catalyzed hydroxysulfenylation of alkenes was achieved using disulfides in the presence of n-Bu4NI and H2O. The procedure smoothly proceeded under air atmosphere, and the corresponding β-hydroxysulfides were obtained with regio- and anti-selectivity in good yields. Furthermore, a reaction using diselenides effectively produced the expected β-hydroxyselenides. These reactions could use both

  在 n-Bu 4 NI 和 H 2 O存在下，铜催化烯烃的羟基亚磺酰化反应，在n- Bu 4 NI 和 H 2 O 存在下，反应过程顺利进行，得到了区域选择性和抗选择性良好的β-羟基硫化物。产量。此外，使用二硒化物的反应有效地产生了预期的β-羟基硒化物。这些反应可以使用二硫属化物上的两个硫属化物基团。此外，该程序还适用于使用硫醇进行的氢化亚磺酰化。
• Oxone Oxidation of Selenides: A Mild and Efficient Method for the Preparation of Selenones
  作者：Paolo Ceccherelli、Massimo Curini、Francesco Epifano、Maria Carla Marcotullio、Ornelio Rosati

  DOI：10.1021/jo00131a018

  日期：1995.12
• A One-Pot Method for the Stereoselective Introduction of a Vinyl Group via an Atom-Transfer Radical-Cyclization Reaction with a Diphenylvinylsilyl Group as a Temporary Connecting Tether. Synthesis of 4‘α-<i>C</i>-Vinylthymidine, a Potent Antiviral Nucleoside¹
  作者：Isamu Sugimoto、Satoshi Shuto、Akira Matsuda

  DOI：10.1021/jo990787f

  日期：1999.9.1

  A one-pot method for the stereoselective introduction of a vinyl group at the beta-position of a hydroxyl group in halohydrins or alpha-phenylselenoalkanols via an atom-transfer radical-cyclization reaction was developed. When a solution of the diphenylvinylsilyl ether of (+/-)-trans-2-iodoindanol (2a) and (Bu3Sn)(2) in benzene was irradiated with a high-pressure mercury lamp, the corresponding atom transfer 5-exo-cyclization product was produced, which in turn was treated with tetrabutylammonium fluoride to give cis-2-vinylindanol (3) in 82% yield from 2a. Similar reactions with diphenylvinylsilyl ethers of (+/-)trans-1-phenylselenoindan-2-ol (4), trans-2-iodocyclopentanol (6), and trans-2-iodocyclohexanol (8) gave the corresponding vinyl derivatives. Furthermore, this reaction was successfully applied to the synthesis of 4'alpha-C-vinylthymidine, a potent antiviral nucleoside.