(1S,2S)-(-)-threo-2-(dimethylamino)1,2-diphenylethanol | 83603-68-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1S,2S)-(-)-threo-2-(dimethylamino)1,2-diphenylethanol
• 英文别名: (-)-threo-2-dimethylamino-1,2-diphenylethanol；(-)-(1S,2S)-N,N-dimethylamino-1,2-diphenylethanol；(1S,2S)-2-(dimethylamino)-1,2-diphenylethanol
• CAS: 83603-68-3
• 化学式: C₁₆H₁₉NO
• 分子量: 241.333
• InChiKey: MLJRRPFUCGOHPB-HOTGVXAUSA-N

物化性质

• 沸点：
  347.9±30.0 °C(Predicted)
• 密度：
  1.085±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-碘苯甲醚 、 (1S,2S)-(-)-threo-2-(dimethylamino)1,2-diphenylethanol 在 copper(l) iodide 、 cerium (III) carbonate 作用下， 以 various solvent(s) 为溶剂， 反应 24.0h， 以82%的产率得到(1S,2S)-1-dimethylamino-2-(2-methoxyphenoxy)-1,2-diphenylethane
  参考文献：
  名称：

  Improved asymmetric synthesis of dopamine D1 full agonist, dihydrexidine, employing chiral ligand-controlled asymmetric conjugate addition of aryllithium to a nitroalkene

  摘要：

  Asymmetric conjugate addition of 2-trityloxymethylpheyllithium to a nitroalkene was mediated by a chiral ligand to give the key intermediate for dopamine D1 full agonist dihydrexidine 1. The shortcut of both Curtius rearrangement and Pictet-Spengler type cyclization, which were the drawback of the previously reported synthesis involving asymmetric conjugate addition of phenyllithium to an enoate, was realized by the newly developed asymmetric reaction. Short and efficient synthetic way gave optically pure dihydrexidine in 45% overall yield via eight steps. Improved synthesis of the best chiral ligand 13 was realized under the Buchwald conditions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.039
• 作为产物：
  描述：

  聚合甲醛 、 (1S,2s)-(-)-2-氨基-1,2-二苯基乙醇 在 甲酸 作用下， 反应 20.0h， 以74%的产率得到(1S,2S)-(-)-threo-2-(dimethylamino)1,2-diphenylethanol
  参考文献：
  名称：

  2-氨基-1,2-二苯乙醇的优先结晶光学拆分及其在前手性酮的分级结晶和对映选择性还原中的应用

  摘要：

  由安息香肟通过催化还原制备的 (±)-erythro-2-Amino-1,2-diphenylethanol 通过优先结晶成功分解为一对旋光形式。发现旋光氨基醇可用作碱性拆分剂，用于旋光拆分酒石酸、反式-2,3-环氧乙烷二甲酸、2-羟基-2-苯基丙酸和 3-endo-benzamido-5-降冰片烯-2-内-羧酸。由氢化铝锂和旋光性苏式-或赤式-2-氨基-1,2-二苯基乙醇衍生物制备的手性氢化物应用于前手性酮的对映面差异化还原，得到相应的旋光醇，其光学纯度为 26-72%。

  DOI：

  10.1246/bcsj.55.1568

文献信息

• PROCESS FOR PREPARATION OF ERIBULIN AND INTERMEDIATES THEREOF
  申请人：DR. REDDY'S LABORATORIES LIMITED

  公开号：US20190276470A1

  公开（公告）日：2019-09-12

  The present application relate to process for preparation of tetrahydrofuran compound of formula II, 4-Methylene tetrahydrofuran compound of formula V and tetrahydropyran compound of formula IX which are useful as intermediates for the preparation of halichondrin B analogues such as Eribulin or its pharmaceutically acceptable salts.

  本申请涉及制备式II的四氢呋喃化合物、式V的4-亚甲基四氢呋喃化合物和式IX的四氢吡喃化合物的工艺，它们是制备半乳糖霉素B类似物如依立必利或其药学上可接受的盐的中间体。
• Enantioselective reaction of an imine with methyllithium catalyzed by a chiral ligand
  作者：Isao Inoue、Mitsuru Shindo、Kenji Koga、Motomu Kanai、Kiyoshi Tomioka

  DOI：10.1016/0957-4166(95)00331-i

  日期：1995.10

  Enantioselective reaction of benzaldehyde 4-anisidineimine 1 with methyllithium in toluene was mediated by a series of chiral aminoethers 3-11 to give the corresponding amine 2 in good to moderate ee. The chiral tridentate aminoethers 7-11 are superior to the bidentate ligands 3-6, Lithium bromide affects significantly the enantioselectivity in the catalytic reaction, but not in the stoichiometric reaction.
• Optical Resolution of 2-Amino-1,2-diphenylethanol by Preferential Crystallization and Its Utilization in Fractional Crystallization and Enantioselective Reduction of Prochiral Ketones
  作者：Kazuhiko Saigo、Shigeo Ogawa、Shigetoshi Kikuchi、Atsushi Kasahara、Hiroyuki Nohira

  DOI：10.1246/bcsj.55.1568

  日期：1982.5

  3-endo-benzamido-5-norbornene-2-endo-carboxylic acid. Chiral hydrides prepared from lithium aluminium hydride and optically active threo- or erythro-2-amino-1,2-diphenylethanol derivatives were applied to the enantioface differentiating reduction of prochiral ketones to give the corresponding optically active alcohols in 26–72% optical purities.

  由安息香肟通过催化还原制备的 (±)-erythro-2-Amino-1,2-diphenylethanol 通过优先结晶成功分解为一对旋光形式。发现旋光氨基醇可用作碱性拆分剂，用于旋光拆分酒石酸、反式-2,3-环氧乙烷二甲酸、2-羟基-2-苯基丙酸和 3-endo-benzamido-5-降冰片烯-2-内-羧酸。由氢化铝锂和旋光性苏式-或赤式-2-氨基-1,2-二苯基乙醇衍生物制备的手性氢化物应用于前手性酮的对映面差异化还原，得到相应的旋光醇，其光学纯度为 26-72%。
• Improved asymmetric synthesis of dopamine D1 full agonist, dihydrexidine, employing chiral ligand-controlled asymmetric conjugate addition of aryllithium to a nitroalkene
  作者：Mitsuaki Yamashita、Ken-ichi Yamada、Kiyoshi Tomioka

  DOI：10.1016/j.tet.2004.03.039

  日期：2004.5

  Asymmetric conjugate addition of 2-trityloxymethylpheyllithium to a nitroalkene was mediated by a chiral ligand to give the key intermediate for dopamine D1 full agonist dihydrexidine 1. The shortcut of both Curtius rearrangement and Pictet-Spengler type cyclization, which were the drawback of the previously reported synthesis involving asymmetric conjugate addition of phenyllithium to an enoate, was realized by the newly developed asymmetric reaction. Short and efficient synthetic way gave optically pure dihydrexidine in 45% overall yield via eight steps. Improved synthesis of the best chiral ligand 13 was realized under the Buchwald conditions. (C) 2004 Elsevier Ltd. All rights reserved.