(-)-dimenthyl diselenide | 910660-26-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-dimenthyl diselenide
• 英文别名: (1S,2R,4R)-4-methyl-2-[[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]diselanyl]-1-propan-2-ylcyclohexane
• CAS: 910660-26-3
• 化学式: C₂₀H₃₈Se₂
• 分子量: 436.442
• InChiKey: VZCUXRISYZDEIR-XRNRSJMDSA-N

物化性质

• 沸点：
  445.6±28.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.07
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (-)-dimenthyl diselenide 在 溴 、 silver trifluoromethanesulfonate 作用下， 以 四氯化碳 、 二氯甲烷 、 甲醇 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Synthesis and reactions of terpenyl diselenides functionalized with phenyl and naphthyl groups

  摘要：

  An efficient methodology for the synthesis of chiral terpenyl diselenides functionalized with phenyl and naphthyl groups has been developed. Using the reaction of sodium diselenide with terpenyl tosylates and chlorides, the corresponding diselenides derived from 8-phenyl menthol and isopinocampheol modified at the 10-position were obtained. Diselenides were transformed into electrophilic selenium reagents and tested in the asymmetric selenenylation of styrene. The effect of aryl groups on the enantioselectivity of the addition reaction was examined. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.02.004
• 作为产物：
  描述：

  neomenthyl chloride 在 sodium hydroxide 、 selenium 、 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以40%的产率得到(-)-dimenthyl diselenide
  参考文献：
  名称：

  新型旋光萜烯二烷基二硒化物的合成与反应

  摘要：

  发现二硒化钠与光学活性的甲苯磺酸烷基酯或氯化物的反应是合成光学活性二烷基二硒化物的有用方法。已经获得衍生自薄荷烷、卡拉烷、蒎烷和冰片烷系统的旋光单萜二硒化物。已经研究了所得二硒化物的萜烯片段对甲氧基硒化产物的非对映体过量的影响。对于 (-)-二异松香叶二硒化物观察到甲氧基硒化的最佳结果。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  DOI：

  10.1002/ejoc.200600044

文献信息

• A Simple Zinc-Mediated Preparation of Selenols
  作者：Claudio Santi、Stefano Santoro、Lorenzo Testaferri、Marcello Tiecco

  DOI：10.1055/s-2008-1078408

  日期：2008.6

  Under acidic conditions zinc reduces diselenides to afford selenols, which can be either isolated or treated in situ with alkyl halides to produce alkyl selenides or with epoxides to give β-hydroxyselenides.

  在酸性条件下，锌可将二硒化合物还原为硒醇，这些硒醇既可分离出来，也可就地与烷基卤反应生成烷基硒醚，或与环氧化物反应得到β-羟基硒醚。
• Synthesis and reactions of the optically active selenols derived from monoterpenes
  作者：Jacek Ścianowski、Jarosław Rafalski、Anna Banach、Justyna Czaplewska、Anna Komoszyńska

  DOI：10.1016/j.tetasy.2013.07.018

  日期：2013.9

  the synthesis of optically active selenols, derived from p-menthane, carane, and pinane, is described. The selenols were oxidized with air to give the optically active diselenides, and were also converted into the corresponding allylic selenides via reaction with Z- and E-cinnamyl, geranyl, and neryl chlorides. Oxidation of the allylic selenides with mCPBA gave the optically active alcohols via [2,3]-sigmatropic

  描述了一种方便的方法，用于合成衍生自对-薄荷烷，han烷和pin烷的旋光硒醇。用空气将硒醇氧化，得到旋光性二硒化物，并通过与Z-和E-肉桂基，香叶基和神经酰氯的反应将其转化为相应的烯丙基硒化物。用m CPBA氧化烯丙基硒化物通过原位生成的烯丙基硒氧化物的[2,3]-σ重排而得到旋光性醇。
• Synthesis of Selenium Derivatives of 3-Hydroxy-2-substituted-2,3-dihydroisoindol-1-ones
  作者：Magdalena Ciechańska、Andrzej Jóźwiak、Jacek Ścianowski

  DOI：10.1080/10426500902947849

  日期：2009.6.23

  Regiospecific transformation of 3-hydroxy-2-substituted-2,3-dihydroisoindol-1-ones into their aryl and alkyl 7-selenium derivatives, via metallation and subsequent reaction with diselenides, is described.
• Asymmetric selenocyclization with the use of dialkyl monoterpene diselenides
  作者：Zbigniew Rafiński、Jacek Ścianowski、Andrzej Wojtczak

  DOI：10.1016/j.tetasy.2007.11.032

  日期：2008.2

  Selenocyclization with the use of the monoterpene diselenides from menthane, carane and pinane groups has been studied. The conditions for asymmetric selenocyclization have been optimized. It has been established that the best enantiomeric excesses were obtained in the case of selenocyclization for the unsubstituted alkyl diselenides with (+)-dineomenthyl diselenide. The results of the selenocyclization of the (+)-dineomenthyl diselenide with the unsaturated alcohols and acids are presented. (C) 2007 Elsevier Ltd. All rights reserved.
• Synthesis and reactions of enantiomerically pure dialkyl diselenides from the p-menthane group
  作者：Zbigniew Rafiński、Jacek Ścianowski

  DOI：10.1016/j.tetasy.2008.04.027

  日期：2008.5

  A convenient route for the synthesis of optically active dialkyl diselenides from the p-menthane system utilizing a reaction of alkyl tosylates and chlorides with sodium diselenide is reported. The diselenides obtained have been used for asymmetric methoxyselenenylation of styrene. Quantum chemical calculations of the chair conformers stability of the terpeneselenenyl bromides from the p-menthane group have also been carried out using density functional theory (DFF, at the B3LYP/6-311G(d) level). The influence of the diselenides structure on the stereoselectivity in the methoxyselenenylation reaction is also discussed. (C) 2008 Elsevier Ltd. All rights reserved.