(1R,2R,3S,5R)-3-氨基-2,6,6-三甲基二环[3.1.1]庚-2-醇 | 168286-10-0

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物
• 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: (1R,2R,3S,5R)-3-氨基-2,6,6-三甲基二环[3.1.1]庚-2-醇
• 中文别名: (1R,2R,3S,5R)-3-氨基-2,6,6-三甲基二环[3.1.1]-2-庚醇
• 英文名称: (1R,2R,3S,5R)-3-amino-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol
• 英文别名: (1R,2R,3S,5R)-3-amino-2,6,6-trimethyl-norpinan-2-ol
• CAS: 168286-10-0
• 化学式: C₁₀H₁₉NO
• 分子量: 169.267
• InChiKey: LGVDAZQPWJBBGX-BDNRQGISSA-N

物化性质

• 沸点：
  239.5±23.0 °C(Predicted)
• 密度：
  1.015±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 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：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S,5R)-3-氨基-2,6,6-三甲基二环[3.1.1]庚-2-醇 在 仲丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (1R,2R,4S,6R,9S,11R)-6-benzyl-2,6,12,12-tetramethyl-4-phenyl-3-oxa-8-azatetracyclo[9.1.1.02,9.04,8]tridecan-7-one
  参考文献：
  名称：

  Complementary Selectivity in the Alkylation of Chiral Bicyclic Lactam Enolates

  摘要：

  DOI：

  10.1021/jo960852a
• 作为产物：
  描述：

  (-)-α-蒎烯 在 potassium permanganate 、 lithium aluminium tetrahydride 、 盐酸羟胺 、 水 、 sodium acetate trihydrate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 (1R,2R,3S,5R)-3-氨基-2,6,6-三甲基二环[3.1.1]庚-2-醇
  参考文献：
  名称：

  衍生自（+）和（-）-α-pine烯的新手性配体，用于将二乙基锌对映体选择性加成到醛中

  摘要：

  在这项研究中，我们从（+）和（-）-α-pine烯合成了五个新的手性配体，这些配体成功地用于将二乙基锌立体选择性地加成到醛中，从而产生仲手性醇，收率高达99％和94％ ee

  DOI：

  10.1016/j.tetlet.2015.12.042

文献信息

• Synthesis of the C1-C14 Fragment of Sarcoglaucol-16-one via Z-Selective Ando-Type Horner-Wadsworth-Emmons Olefination
  作者：Sabine Laschat、Christoph Gastl

  DOI：10.1055/s-0029-1218825

  日期：2010.8

  A synthetic strategy involving a Z-selective Horner-Wadsworth-Emmons olefination was developed for the preparation of the sarcoglaucolone precursor methyl (2Z,6E)-8-(methoxymeth­oxy)-6-methyl-2-[(3E)-4-methyl-5-oxopent-3-enyl]-9-[(trimethylsilyl)methyl]deca-2,6,9-trienoate. The target compound was isolated in a E/Z ratio of 17:83

  开发了一种涉及Z选择性Horner-Wadsworth-Emmons烯烃化的合成策略，用于制备sarcoglaucolone前体——甲基(2Z,6E)-8-(甲氧基甲氧基)-6-甲基-2-[(3E)-4-甲基-5-氧戊-3-烯基]-9-[(三甲基硅基)甲基]癸-2,6,9-三烯酸酯。目标化合物以E/Z比率17:83被分离。
• Chiral terpene auxiliaries II. Spiroborate esters derived from α-pinene—new catalysts for asymmetric borane reduction of prochiral ketones
  作者：Marek P. Krzemiński、Marta Ćwiklińska

  DOI：10.1016/j.tetlet.2011.05.095

  日期：2011.7

  New spiroborate esters derived from (1R,2R,3S,5R)-3-aminopinan-2-ol and ethylene glycol, propane-1,3-diol, pinacol, catechol, (1S,2S,3R,5S)-pinane-2,3-diol, and (1R,2R,3S,5R)-pinane-2,3-diol were used as catalysts in the borane reduction of acetophenone and other prochiral aryl alkyl ketones producing the corresponding alcohols in high yields. The influence of the spiroborate structure on the enantioselectivity

  由（1 R，2 R，3 S，5 R）-3-氨基pinan-2-ol和乙二醇，1,3-丙二醇，频哪醇，邻苯二酚，（1 S，2 S，3 R，5 S）-pin烷-2,3-二醇和（1 R，2 R，3 S，5 R）-pin烷-2,3-二醇被用作苯乙酮和其他前手性芳基的硼烷还原催化剂烷基酮以高收率生产相应的醇。研究了螺硼酸酯结构对产物醇的对映选择性和构型的影响。
• A practical method for preparation of optically pure oxazaborolidines from α-Pinene
  作者：Moriyasu Masui、Takayuki Shioiri

  DOI：10.1016/0040-4020(95)00447-g

  日期：1995.7

  (1S,2S,3R,5S)- and (1S,2S,3R,5S)-3-Amino-2-hydroxypinane (1 and 2) were prepared from the corresponding a-pinene in optically pure form. They and their derivatives reacted with various organoborane compounds. A variety of chiral oxazaborolidines 3a-e and 4 were obtained in high yield.

  (1S,2S,3R,5S)-和(1S,2S,3R,5S)-3-氨基-2-羟基蒎烷（1和2）以光学纯形式由相应的α-蒎烯制备。它们及其衍生物与各种有机硼化合物反应，获得多种高产率的轴重环状化合物3a-e和4。
• Synthesis and evaluation of the antioxidant properties for some novel aminomethyl derivatives of 2,6-diisobornylphenol bearing a pinane moiety
  作者：I. A. Dvornikova、E. V. Buravlev、O. G. Shevchenko、I. Yu. Chukicheva、A. V. Kutchin

  DOI：10.1007/s11172-021-3330-0

  日期：2021.11

  Some new derivatives based on 2,6-diisobornylphenol and containing amine moieties of the pinane structure at the para-position relative to the phenolic hydroxy group were synthesized. The antioxidant properties of the obtained compounds were estimated using various in vitro models. The introduction of diamine moiety into a starting molecule led to a significant increase in the radical scavenging activity

  合成了一些基于2,6-二异冰片基苯酚并在相对于酚羟基的对位含有蒎烷结构的胺部分的新衍生物。使用各种体外模型估计所得化合物的抗氧化特性。将二胺部分引入起始分子中导致自由基清除活性和螯合Fe 2+离子的能力显着增加。
• Catalytic enantioselective borane reduction of arylketones with pinene-derived amino alcohols
  作者：Dennis Hobuß、Angelika Baro、Sabine Laschat、Wolfgang Frey

  DOI：10.1016/j.tet.2007.12.020

  日期：2008.2

  Both cis- and trans-1,2-amino alcohols 5 and their N-alkylated derivatives 6 were prepared from (-)-alpha-pinene 7 as chirality source and utilized in asymmetric borane reduction of arylketones 12 employing a one-pot multi-substrate screening. The oxazaborolidine catalysts were generated in situ from amino alcohols 5 and 6 and trimethyl borate. (C) 2008 Elsevier Ltd. All rights reserved.