(1R,3S,4S)-2-azabicyclo<2.2.1>heptane-3-exo-diphenylmethanol | 169888-75-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,3S,4S)-2-azabicyclo<2.2.1>heptane-3-exo-diphenylmethanol
• 英文别名: (1R,3S,4S)-2-azabicyclo[2.2.1]heptane-3-exo-diphenylmethanol；[(1R,3S,4S)-2-azabicyclo[2.2.1]heptan-3-yl]-diphenylmethanol
• CAS: 169888-75-9
• 化学式: C₁₉H₂₁NO
• 分子量: 279.382
• InChiKey: XOYJAFGAWSBPTI-QGTPRVQTSA-N

物化性质

• 熔点：
  133-134 °C
• 沸点：
  441.4±12.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 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,3S,4S)-2-azabicyclo<2.2.1>heptane-3-exo-diphenylmethanol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 15.0h， 生成 (1R,3R,6S,7S)-3-(2-hydroxymethylphenyl)-5-diphenyl-4-oxa-2-azatricyclo[5.2.1.0^2,6]decane
  参考文献：
  名称：

  Synthesis of New Chiral Catalysts, 2-Azanorbornyloxazolidines, for Enantioselective Addition of Diethylzinc to Aldehydes

  摘要：

  DOI：

  10.3987/com-99-s(i)4
• 作为产物：
  描述：

  (1S,3S,4R)-2-((R)-1-苯乙基)-2-氮杂双环[2.2.1]庚-5-烯-3- 在 palladium dihydroxide 、 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 96.0h， 生成 (1R,3S,4S)-2-azabicyclo<2.2.1>heptane-3-exo-diphenylmethanol
  参考文献：
  名称：

  使用2-氮杂降冰片基甲醇和2-氮杂降冰片基甲硫醇作为催化剂，将二乙基锌对醛进行对映选择性加成

  摘要：

  由乙基（1 S，3 S，4 R）-2-[（（R）-1-苯基乙基）-2-氮杂双环[2.2.1]庚-5-烯- 3-羧酸酯化并催化二乙基锌对醛的对映选择性加成，得到旋光性仲醇。

  DOI：

  10.1016/s0957-4166(97)00118-3
• 作为试剂：
  描述：

  5-氟靛红 、 环己酮 在 (1R,3S,4S)-2-azabicyclo<2.2.1>heptane-3-exo-diphenylmethanol 、 三氟乙酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以32%的产率得到
  参考文献：
  名称：

  2-Azanorbornane-based amine organocatalyst for enantioselective aldol reaction of isatins with ketones

  摘要：

  Optically active 2-azanorbornane-based organocatalysts were designed and synthesized, and the catalytic activity of these catalysts in enantioselective aldol reactions of isatins with ketones was investigated. Among these catalysts, 2-azanorbornylmethanol showed the best catalytic activity to afford the corresponding aldol product in excellent chemical yield (up to 95%) and with moderate stereoselectivity (up to 64% ee, up to syn:anti = 36:64). (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.08.013

文献信息

• Enantioselective epoxidation of α,β-enones promoted by (1R,3S,4S)-2-azanorbornyl-3-methanol as an organocatalyst
  作者：Jun Lu、Yun-He Xu、Feng Liu、Teck-Peng Loh

  DOI：10.1016/j.tetlet.2008.07.175

  日期：2008.10

  (1R,3S,4S)-2-Azanorbornyl-3-methanol was synthesized form (R)-1-phenylethylamine and used as a catalyst for the enantioselective epoxidation of α,β-enones to afford the corresponding epoxides in good yields and high enantioselectivities at room temperature.

  （R）-1-苯基乙胺合成了（1 R，3 S，4 S）-2-氮杂降冰片基-3-甲醇，用作α，β-烯酮的对映选择性环氧化的催化剂，可得到良好的相应环氧化物在室温下收率和高对映选择性。
• New chiral ligands, pyrrolidinyl- and 2-azanorbornyl- phosphinooxazolidines for palladium-catalyzed asymmetric allylation
  作者：Yuko Okuyama、Hiroto Nakano、Hiroshi Hongo

  DOI：10.1016/s0957-4166(00)00049-5

  日期：2000.3

  Pyrrolidinyl-2 and 2-azanorbornylphosphinooxazolidines 3, a new type of optically active ligands, were synthesized easily and their abilities as ligands were examined in Pd-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate. Enantiomeric excesses of up to 96% have been obtained using 1 mol% of [PdCl(eta(3)-C3H5)](2) and 2.1 mol% of 2. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Nakano, Hiroto; Okuyama, Yuko; Fushimi, Kazuyuki, Heterocycles, 2002, vol. 56, # 1-2, p. 457 - 466
  作者：Nakano, Hiroto、Okuyama, Yuko、Fushimi, Kazuyuki、Yamakawa, Ryo、Kayaoka, Daisuke、Hongo, Hiroshi

  DOI：——

  日期：——
• Synthesis of new chiral catalysts, N-alkyl-2-azanorbornyl-methanols, for the enantioselective addition of diethylzinc to arylaldehydes
  作者：Hiroto Nakano、Noriyuki Kumagai、Chizuko Kabuto、Hisao Matsuzaki、Hiroshi Hongo

  DOI：10.1016/0957-4166(95)00151-e

  日期：1995.6

  New chiral ligands, 2-azanorbornylmethanols, were prepared and catalyzed the addition of diethylzinc to aldehydes to furnish secondary alcohols in up to 92%ee.
• 2-Azanorbornane-based amine organocatalyst for enantioselective aldol reaction of isatins with ketones
  作者：Ayumi Ogasawara、U.V. Subba Reddy、Chigusa Seki、Yuko Okuyama、Koji Uwai、Michio Tokiwa、Mitsuhiro Takeshita、Hiroto Nakano

  DOI：10.1016/j.tetasy.2016.08.013

  日期：2016.11

  Optically active 2-azanorbornane-based organocatalysts were designed and synthesized, and the catalytic activity of these catalysts in enantioselective aldol reactions of isatins with ketones was investigated. Among these catalysts, 2-azanorbornylmethanol showed the best catalytic activity to afford the corresponding aldol product in excellent chemical yield (up to 95%) and with moderate stereoselectivity (up to 64% ee, up to syn:anti = 36:64). (C) 2016 Elsevier Ltd. All rights reserved.