(1R,2R,3S,4S)-3-methylamino-1,7,7-trimethylbicyclo<2.2.1>heptan-2-ol | 131433-45-9

• 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: (1R,2R,3S,4S)-3-methylamino-1,7,7-trimethylbicyclo<2.2.1>heptan-2-ol
• 英文别名: cis-endo-N-monomethyl-3-aminoborneol；(1R)-3endo-methylamino-bornane-2endo-ol；(1R)-3endo-Methylamino-bornan-2endo-ol；(1R)-3endo-Methylamino-bornanol-(2endo)；(1R,2R,3S,4S)-1,7,7-trimethyl-3-(methylamino)bicyclo[2.2.1]heptan-2-ol
• CAS: 131433-45-9
• 化学式: C₁₁H₂₁NO
• 分子量: 183.294
• InChiKey: ZGDBAXYRLDIMOH-HJGDQZAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.26
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S,4S)-3-methylamino-1,7,7-trimethylbicyclo<2.2.1>heptan-2-ol 在 chromium(VI) oxide 作用下， 生成 3-endo-Methylaminobornan-2-on
  参考文献：
  名称：

  Mazza; Migliardi, Chemische Berichte, 1939, vol. 72, p. 689,691,694

  摘要：

  DOI：
• 作为产物：
  描述：

  3-endo-Methylaminobornan-2-on 在 sodium 、 苯 作用下， 生成 (1R,2R,3S,4S)-3-methylamino-1,7,7-trimethylbicyclo<2.2.1>heptan-2-ol
  参考文献：
  名称：

  欧盟经济研究基金会巴恩·奥夫·坎佩尔奇农二世（Bain auf Campherchinon II）

  摘要：

  DOI：

  10.1002/hlca.193702001153

文献信息

• Asymmetric synthesis of (R)-(–)- and (S)-(+)-muscone by enantioselective conjugate addition of chiral dimethylcuprate to (E)-cyclopentadec-2-en-1-one
  作者：Kazuhiko Tanaka、Hideki Ushio、Yasuyuki Kawabata、Hitomi Suzuki

  DOI：10.1039/p19910001445

  日期：——

  configuration of the chiral ligand used. Thus the conjugate addition using the ligand prepared from exo-3-monosubstituted-amino-exo-2-hydroxybornane gave (S)-(+)-muscone, while with endo-ligand, (R)-(–)-muscone was obtained in higher enantioselectivity. Muscone of essentially 100% optical purity was obtained by the addition of small amounts of THF (tetrahydro-furan)(2–10 equiv.) to the toluene solution

  已经从樟脑制备了多种旋光性仲氨基醇，并在缀合物加成反应中将其筛选为手性不可转移的铜酸盐配体。（E）-环戊二烯-2-烯-1-酮与甲苯中配体衍生的手性二甲基杯酸酯的反应，对映体过量的muscone含量高达26-89％。产物的立体化学与所用手性配体的构型有关。因此，使用由exo -3-单取代-氨基-exo -2-羟基冰片烷制备的配体进行共轭物加成，得到（S）-（+）-muscone，而带有内-配体，（R）-（-）-muscone的对映选择性更高。通过向由（1 R，2 R，3 S， 4 S）-3-[（（1-甲基吡咯-2-基）甲基氨基] -1,7,7-三甲基双环[2.2.1]庚烷-2-醇23（内-MPATH）。简要研究了手性配体和铜酸盐试剂的化学计量对化学收率和对映选择性的影响。
• (+)-Camphor-derived tri- and tetradentate amino alcohols; synthesis and application as ligands in the nickel catalyzed enantioselective conjugate addition of diethylzinc
  作者：AndréH.M. de Vries、Rosalinde Imbos、Ben L. Feringa

  DOI：10.1016/s0957-4166(97)00145-6

  日期：1997.5

  Several novel tri- and tetradentate amino alcohol ligands, all derived from (+)-camphor, have been synthesized by using specific N-alkylation procedures. The amino alcohols were employed as chiral ligands in the nickel catalyzed conjugate additions of diethylzine to chalcone and cyclohexenone as model substrates. For the acyclic enone enantioselectivities up to 83% were achieved. (C) 1997 Elsevier Science Ltd.
• Henin Francoise, MBoungo-MPassi Athanase, Muzart Jacques, Pete Jean-Pierr+, Tetrahedron, 50 (1994) N 9, S 2849- 2864
  作者：Henin Francoise, MBoungo-MPassi Athanase, Muzart Jacques, Pete Jean-Pierr+

  DOI：——

  日期：——