3,8,8-三甲基-4-氧杂三环[5.1.0.03,5]辛烷 | 936-92-5

• 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
• 中文名称: 3,8,8-三甲基-4-氧杂三环[5.1.0.03,5]辛烷
• 英文名称: (1S,3R,4S,6R)-3,4-epoxy-3,7,7-trimethylbicyclo[4.1.0]heptane
• 英文别名: (-)-(1S,3R,4S,6R)-3,4-epoxy-3,7,7-trimethylbicyclo[4.1.0]heptane；β-cis-3,4-Epoxycarane；(-)-β-3,4-epoxycarane；Δ³-carene；β-3,4-epoxycarane；cis-(+)-3-carene epoxide；(1S,3R,5S,7R)-3,8,8-trimethyl-4-oxatricyclo[5.1.0.03,5]octane
• CAS: 936-92-5
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: AGHSZSJVJPSERC-CHIQAWFVSA-N

物化性质

• 沸点：
  69-70 °C(Press: 10 Torr)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  3,8,8-三甲基-4-氧杂三环[5.1.0.03,5]辛烷 在 sodium selenide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 以57%的产率得到(1S,3R,1'S,3'R)-(-)-bis(3-hydroxy-4-isocaranyl)selenide
  参考文献：
  名称：

  Syntheses and reactions of terpene β-hydroxyselenides and β-hydroxydiselenides

  摘要：

  A convenient method for the synthesis of optically active trans-hydroxyselenides and trans-hydroxydiselenides from the bicyclic terpene group based on the reactions of sodium selenide or sodium diselenide with cis- and trans-(+)-3-carane, trans-(+)-2-carane and (-)-beta-pinane epoxides is described. The corresponding cis-hydroxy and cis-methoxydiselenides were obtained in the reaction of sodium diselenide with beta-hydroxy- and beta-methoxytosylates. The influence of a hydroxy group at the beta-position on the diastereomeric ratio of the products of the asymmetric methoxyselenenylation of styrene has been established by composition of the products, crystal structure analyses, and theoretical calculations using a DFT method on the B3LYP level (6-311G(d)). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.001
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 、 对甲苯磺酰氯 作用下， 生成 3,8,8-三甲基-4-氧杂三环[5.1.0.03,5]辛烷
  参考文献：
  名称：

  Kuczynski; Chabudzinski, Roczniki Chemii, 1960, vol. 34, p. 177,185

  摘要：

  DOI：

文献信息

• Syntheses of the Optically Active Terpene Hydroxyphenylselenides
  作者：Jacek Ścianowski、Mirosław Wełniak

  DOI：10.1080/10426500902947682

  日期：2009.6.23

  The optically active hydroxyphenylselenides derived from the p-menthane, carane, and pinane systems have been obtained. Two methods of hydroxyphenylselenides synthesis have been compared. The first method is based on the reaction of alkenes with N-(phenylseleno)succinimide in the presence of water, and the second from epoxides as a result of the reaction with sodium benzeneselenolate. The influence

  已经获得了衍生自对薄荷烷、卡拉烷和蒎烷体系的旋光羟基苯硒化物。已经比较了羟苯基硒化物的两种合成方法。第一种方法基于烯烃与 N-(苯基硒基)琥珀酰亚胺在水存在下的反应，第二种方法是与苯硒酸钠反应产生的环氧化物。已经证明了基材结构对所得产品组成的影响。
• Stereoselective Synthesis of Carane-Type Hydroxythiols and Disulfides Based on Them
  作者：O. A. Banina、D. V. Sudarikov、P. A. Slepukhin、L. L. Frolova、A. V. Kuchin

  DOI：10.1007/s10600-016-1605-8

  日期：2016.3

  Isomeric 10-sulfanylcaran-4-ols and 4-sulfanylcaran-3-ols were synthesized and used to prepare disulfides in high yields.

  合成了异构体10-硫烷基卡朗-4-醇和4-硫烷基卡朗-3-醇，并用于高产率制备二硫化物。
• Reaction of Alkenes with Hydrogen Peroxide and Sodium Iodide: A Nonenzymatic Biogenic-Like Approach to Iodohydrins
  作者：José Barluenga、María Marco-Arias、Francisco González-Bobes、Alfredo Ballesteros、José M. González

  DOI：10.1002/chem.200305582

  日期：2004.4.2

  An efficient protocol to synthesize iodohydrins from alkenes is presented. Reactions were conducted in aqueous media using safe and readily available sodium iodide (the most abundant form of the element), and a highly convenient oxidant such as hydrogen peroxide. Addition of a protic acid triggers a faster and efficient process, a role formally related to that played by haloperoxidase enzymes in naturally

  提出了从烯烃合成碘代醇的有效方案。反应使用安全易得的碘化钠（元素的最丰富形式）和高度方便的氧化剂（如过氧化氢）在水性介质中进行。质子酸的添加会触发更快，更有效的过程，这一作用与卤代过氧化物酶在自然发生的转化中所起的作用正式相关。还讨论了将这些条件成功应用于多克级制剂和天然产物衍生物的过程。
• Carane amino alcohols as organocatalysts in asymmetric aldol reaction of isatin with acetone
  作者：O. A. Banina、D. V. Sudarikov、A. G. Nigmatov、L. L. Frolova、P. A. Slepukhin、S. G. Zlotin、A. V. Kutchin

  DOI：10.1007/s11172-017-1730-y

  日期：2017.2

  Carane-derived β-amino alcohols with amino and hydroxy groups at positions 3 and 4 differing in their mutual arrangement and configuration were synthesized. Their application as organocatalysts in the asymmetric aldol reaction of isatin with acetone allowed one to obtain adducts with up to 84% enantiomeric excess.

  合成了在位置 3 和 4 具有不同的相互排列和构型的氨基和羟基的 Carane 衍生的 β-氨基醇。它们在靛红与丙酮的不对称醛醇反应中作为有机催化剂的应用使人们能够获得对映体过量高达 84% 的加合物。
• Synthesis of amino derivatives of caranol by the addition of cyclic amines to 3-carene oxides
  作者：I. V. Fedyunina、V. V. Plemenkov、G. Sh. Bikbulatova、L. E. Nikitina、I. A. Litvinov、O. N. Kataeva

  DOI：10.1007/bf00630168

  日期：——

  Addition reactions of cyclic amines (morpholine, piperidine) to oxides of 3-carene in the presence of water have been studied. The reactions take place regio- and stereoselectively with the formation of amino derivatives of the carane series.

  已经研究了环胺（吗啉、哌啶）在水存在下与 3-carene 的氧化物的加成反应。反应发生区域选择性和立体选择性，形成卡拉烷系列的氨基衍生物。