(1R,2R,3S,5R)-(2-氨基-2,6,6-三甲基-双环[3.1.1]庚-3-基)-甲醇 | 327611-76-7

• 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)-(2-氨基-2,6,6-三甲基-双环[3.1.1]庚-3-基)-甲醇
• 英文名称: (1R,2R,3S,5R)-2-amino-3-hydroxymethyl-2,6,6-trimethylbicyclo[3.1.1]heptane
• 英文别名: (1R,2R,3S,5R)-2-amino-3-hydroxymethylpinane；(1R,2R,3S,5R)-(2-Amino-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-methanol；[(1R,2R,3S,5R)-2-amino-2,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]methanol
• CAS: 327611-76-7
• 化学式: C₁₁H₂₁NO
• 分子量: 183.294
• InChiKey: VETFELSGHLFPFA-SJQPAMGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 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)-(2-氨基-2,6,6-三甲基-双环[3.1.1]庚-3-基)-甲醇 在 碘甲烷 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 10.0h， 生成 (1R,2R,7S,9R)-4-phenylimino-2,10,10-trimethyl-5-oxa-3-azatricyclo[7.1.1.0^2,7]undecane
  参考文献：
  名称：

  Synthesis and transformations of enantiomeric 1,2-disubstituted monoterpene derivatives

  摘要：

  Regio- and stereospecific addition of chlorosulfonyl isocyanate to (+)- and (-)-alpha -pinene I resulted in enantiomerically pure beta -lactams 2, which were converted to enantiomeric beta -amino esters 3 and 1,3-amino alcohols 4 and 6 with ee >99%. The resulting 1,3-difunctional compounds 3, 4 and 6 were transformed to fused saturated 1,3-heterocycles such as tetrahydro-1,3-oxazines 7 and 9, 2,4-pyrimidinedione 11 and 2-thioxopyrimidin-4-one 13 enantiomers. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00435-3
• 作为产物：
  描述：

  (1R,2R,5S,7R)-2,8,8-trimethyl-4-oxo-3-azatricyclo[5.1.1.02,5]nonane-3-sulfonyl chloride 在 盐酸 、 lithium aluminium tetrahydride 、 potassium hydroxide 、 sodium sulfite 作用下， 生成 (1R,2R,3S,5R)-(2-氨基-2,6,6-三甲基-双环[3.1.1]庚-3-基)-甲醇
  参考文献：
  名称：

  Synthesis, Antimicrobial Evaluation, and Structure–Activity Relationship of α-Pinene Derivatives

  摘要：

  Several (+)- and (-)-alpha-pinene derivatives were synthesized and evaluated for their antimicrobial activity toward Gram-positive bacteria Micrococcus luteus and Staphylococcus aureus, Gram-negative bacterium Escherichia coli, and the unicellular fungus Candida albicans using bioautographic assays. (+)-alpha-Pinene 1a showed modest activity against the test organisms, whereas (-)-alpha-pinene 1b showed no activity at the tested concentration. Of all the alpha-pinene derivatives evaluated, the beta-lactam derivatives (10a and 10b) were the most antimicrobial. The increase in the antimicrobial activity of 10a compared to la ranged from nearly 3.5-fold (C. albicans) to 43-fold (S. aureus). The mean +/- standard deviation for the zone of inhibition (mm) for 10a (C. albicans) was 31.9 +/- 4.3 and that for S. aureus was 51.1 +/- 2.9. Although (-)-alpha-pinene 1b was not active toward the test microorganisms, the corresponding beta-lactam 10b, amino ester 13b, and amino alcohol 14b showed antimicrobial activity toward the test microorganisms. The increase in the antimicrobial activity of lob compared to 1b ranged from 32-fold (S. aureus) to 73-fold (M. luteus). The mean +/- standard deviation for the zone of inhibition (mm) for 10b (S. aureus) was 32.0 +/- 0.60 and that for M. luteus was 73.2 +/- 0.30.

  DOI：

  10.1021/jf403586t

文献信息

• Enantioselective addition of diethylzinc to aldehydes catalyzed by γ-amino alcohols derived from (+)- and (−)-α-pinene
  作者：Zsolt Szakonyi、Árpád Balázs、Tamás A. Martinek、Ferenc Fülöp

  DOI：10.1016/j.tetasy.2005.12.011

  日期：2006.1

  Primary, secondary and tertiary γ-amino alcohols 4, 5, 7 and 9 and 1,3-diamine 6 were synthesized from (+)- and (−)-α-pinene 1 via chiral N-Boc β-amino ester 3a and carboxamide 3b. The amino alcohols and diamine obtained were applied as chiral catalysts in the enantioselective addition of diethylzinc to aromatic aldehydes, resulting in chiral 1-aryl-1-propanols. The first evidence of the substituent-dependent

  伯，仲和叔γ-氨基醇4，5，7和9和1,3-二胺6购自（+）合成-和（ - ） - α蒎烯1通过手性Ñ -Bocβ氨基酯3A和羧酰胺3b。所获得的氨基醇和二胺在将二乙基锌对映体选择性加成到芳族醛中时用作手性催化剂，得到手性的1-芳基-1-丙醇。观察到1，3-氨基醇催化剂的取代基依赖性对映选择性的第一个证据，并且该现象是通过从头算水平使用分子模型来解释的。
• New chiral Schiff bases derived from (+)- and (−)-α-pinenes in the metal complex catalyzed asymmetric oxidation of sulfides
  作者：E. A. Koneva、K. P. Volcho、D. V. Korchagina、N. I. Komarova、A. I. Kochnev、N. F. Salakhutdinov、A. G. Tolstikov

  DOI：10.1007/s11172-008-0017-8

  日期：2008.1

  New chiral Schiff bases were derived from (+)- and (−)-α-pinenes for the first time. Coordinated to vanadium ions, they can be used as ligands in catalytic oxidation of sulfides into chiral sulfoxides. Conditions for the asymmetric oxidation of thioanisole to methyl phenyl sulfoxide in optical purity up to 32% were found. Variation of substituents in the ligand has a significant effect not only on

  新的手性席夫碱首次由 (+)- 和 (-)-α-蒎烯衍生而来。它们与钒离子配位，可用作将硫化物催化氧化为手性亚砜的配体。发现了将苯硫醚不对称氧化为光学纯度高达 32% 的甲基苯基亚砜的条件。配体中取代基的变化不仅对反应的对映选择性有显着影响，而且对形成的亚砜的绝对构型也有显着影响。
• Stereoselective Synthesis and Cytoselective Toxicity of Monoterpene-Fused 2-Imino-1,3-thiazines
  作者：Zsolt Szakonyi、István Zupkó、Reijo Sillanpää、Ferenc Fülöp

  DOI：10.3390/molecules191015918

  日期：——

  Starting from pinane-, apopinane- and carane-based 1,3-amino alcohols obtained from monoterpene-based β-amino acids, a library of monoterpene-fused 2-imino-1,3-thiazines as main products and 2-thioxo-1,3-oxazines as side-products were prepared via two- or three-step syntheses. When thiourea adducts prepared from 1,3-amino alcohols and aryl isothiocyanates were reacted with CDI under mild conditions, O-imidazolylcarbonyl intermediates were isolated which could be transformed to the desired 1,3-thiazines under microwave conditions. 1,3-Thiazines and 2-thioxo-1,3-oxazine side-products could also be prepared in one-step reactions through the application of CDI and microwave irradiation. The ring-closure process was extended to cycloalkane-based γ-hydroxythioureas. The carane- and apopinane-based derivatives exhibited marked antiproliferative activity against a panel of human adherent cancer cell lines (HeLa, A2780, MCF7 and A431).

  以基于单萜的β-氨基酸获得的蒎烷、阿蒎烷和卡烷为基础的1,3-氨基醇为原料，以单萜稠合的2-亚氨基-1,3-噻嗪为主要产品，并以2-硫代-通过两步或三步合成制备副产物 1,3-恶嗪。当由1,3-氨基醇和异硫氰酸芳基酯制备的硫脲加合物与CDI在温和条件下反应时，分离出O-咪唑基羰基中间体，该中间体可以在微波条件下转化为所需的1,3-噻嗪类化合物。 1,3-噻嗪和2-硫代-1,3-恶嗪副产物也可以通过CDI和微波辐射的一步反应制备。闭环过程扩展到基于环烷烃的γ-羟基硫脲。基于carane和apopinane的衍生物对一组人类贴壁癌细胞系（HeLa、A2780、MCF7和A431）表现出显着的抗增殖活性。