(1R,2R,3R,5R)-3-(benzylamino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol | 1013027-63-8

• 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: (1R,2R,3R,5R)-3-(benzylamino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol
• 英文别名: (1R,2R,3R,5R)-3-(benzylamino)-2,6,6-trimethylbicyclo[3.1.1]heptane-2-ol
• CAS: 1013027-63-8
• 化学式: C₁₇H₂₅NO
• 分子量: 259.392
• InChiKey: XUQZZKNDHDNBMZ-KCYZZUKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R,3R,5R)-3-(benzylamino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 以100%的产率得到(1R,2R,3R,5R)-3-amino-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol
  参考文献：
  名称：

  Catalytic enantioselective borane reduction of arylketones with pinene-derived amino alcohols

  摘要：

  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.

  DOI：

  10.1016/j.tet.2007.12.020
• 作为产物：
  描述：

  (1R,2R,5R)-(+)-2-羟基-3-蒎烷酮 、 苄胺 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以79%的产率得到(1R,2R,3R,5R)-3-(benzylamino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol
  参考文献：
  名称：

  Catalytic enantioselective borane reduction of arylketones with pinene-derived amino alcohols

  摘要：

  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.

  DOI：

  10.1016/j.tet.2007.12.020

文献信息

• Palladium complexes with terpene derivatives of ethylenediamine and benzylamine: Synthesis and study of antitumor properties
  作者：O.A. Zalevskaya、Y.A. Gur'eva、A.V. Kutchin、Yu.R. Aleksandrova、E.Yu. Yandulova、N.S. Nikolaeva、M.E. Neganova

  DOI：10.1016/j.ica.2021.120593

  日期：2021.11

  The synthesis of new terpene ligands and palladium complexes based on them has been described. The stereoselective synthesis of new derivatives (−)-(1R,4S)-camphorquinone and N,N-dimethylethylenediamine (1 and 2) and palladium chelate complexes (3 and 4) based on them is presented. It was found that the direct cyclometallation of (1R,2R,3R,5R)-3-(benzylamino)-2,6,6-trimethylbicyclo[3.1.1]heptane-2-ol

  已经描述了新的萜配体和基于它们的钯配合物的合成。提出了基于它们的新衍生物 (-)-(1 R ,4 S )-樟脑醌和N , N-二甲基乙二胺( 1和2 ) 和钯螯合物 ( 3和4 )的立体选择性合成。发现(1 R ,2 R ,3 R ,5 R )-3-(苄氨基)-2,6,6-三甲基双环[3.1.1]庚烷-2-醇( 5)与钯的直接环金属化醋酸盐导致钯环6的形成. 的新的（细胞毒活性3,4,6）和先前描述的（7 - 14）的各种类型的钯络合物进行了研究。对肿瘤来源的各种细胞系（肺腺癌 A549、神经母细胞瘤 SH-SY5Y、喉表皮样 Hep-2 和宫颈癌 HeLa 细胞）进行了毒性作用的研究。据发现，钯络合物6 - 10与和苄胺的萜烯衍生物的复合物11与N，N，O-供体配体的萜烯有最显着的抗肿瘤特性。对于11，在所有细胞系中都发现了细胞毒性效应 IC 50的最低值，尤其是与 SH-SY5Y（IC50