(+)-dineomenthyl diselenide | 910660-22-9

• 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: (+)-dineomenthyl diselenide
• 英文别名: (1S,2S,4R)-4-methyl-2-[[(1S,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]diselanyl]-1-propan-2-ylcyclohexane
• CAS: 910660-22-9
• 化学式: C₂₀H₃₈Se₂
• 分子量: 436.442
• InChiKey: VZCUXRISYZDEIR-MILMJNAHSA-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：

  (+)-dineomenthyl diselenide 在 sodium tetrahydroborate 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 生成 (1S,2S,5R)-(+)-neomenthyl selenol
  参考文献：
  名称：

  Chirality transfer through sulfur or selenium to chiral propellers

  摘要：

  通过ECD方法和DFT计算，立体和电子效应对三苯甲基基团结构的手性转移的影响。

  DOI：

  10.1039/c5ra14072b
• 作为产物：
  描述：

  (1Alpha,2Alpha,5β)-(+-)-5-甲基 在 吡啶 、 sodium diselenide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (+)-dineomenthyl diselenide
  参考文献：
  名称：

  Chirality transfer through sulfur or selenium to chiral propellers

  摘要：

  通过ECD方法和DFT计算，立体和电子效应对三苯甲基基团结构的手性转移的影响。

  DOI：

  10.1039/c5ra14072b

文献信息

• Syntheses and Reactions of New Optically Active Terpene Dialkyl Diselenides
  作者：Jacek Ścianowski、Zbigniew Rafiński、Andrzej Wojtczak

  DOI：10.1002/ejoc.200600044

  日期：2006.7

  The reaction of sodium diselenide with optically active alkyl tosylates or chlorides is found to be a useful method for the synthesis of optically active dialkyl diselenides. Optically active monoterpene diselenides derived from menthane, carane, pinane, and bornane systems have been obtained. The influence of the terpene fragment of the obtained diselenides on the diastereomeric excess of the methoxyselenylation

  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)
• 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。
• Epimerization of <i>trans</i>‐Cycloalkenes with the X−C=C−SeR*‐Unit – The Steric Demand of X=H, F, Cl, Br, I, Me, Et and CF₃
  作者：Helmut Poleschner、Matthias Heydenreich、Andreas J. Achazi

  DOI：10.1002/ejoc.202300838

  日期：2023.11.14

  The ring inversion of trans-cycloalkenes, ring sizes 9–20, investigated with temperature variable 13C NMR spectroscopy, is a highly sensitive method to characterize the steric demand of substituents: H≪F≪Cl

  环尺寸为9-20 的反式环烯烃的环反转，通过温度可变13 C NMR 光谱进行研究，是一种表征取代基空间需求的高度灵敏的方法：H≪F≪Cl
• 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.