(1S,2S)-1-phenyl-2-(pyrrolidin-1-yl)propan-1-ol | 1771698-89-5

• 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: (1S,2S)-1-phenyl-2-(pyrrolidin-1-yl)propan-1-ol
• 英文别名: 1-Phenyl-2-(pyrrolidin-1-yl)propan-1-ol, (1S,2S)-；(1S,2S)-1-phenyl-2-pyrrolidin-1-ylpropan-1-ol
• CAS: 1771698-89-5
• 化学式: C₁₃H₁₉NO
• 分子量: 205.3
• InChiKey: FZVHJGJBJLFWEX-WCQYABFASA-N

物化性质

• 沸点：
  321.3±22.0 °C(Predicted)
• 密度：
  1.075±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  (1S,2S)-1-phenyl-2-(pyrrolidin-1-yl)propan-1-ol 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 40.5h， 生成 (1S,2S)-N-methyl-1-phenyl-2-(1-pyrrolidinyl)-1-propanamine
  参考文献：
  名称：

  Enantioselective rearrangement of a meso-cyclohexene oxide using norephedrine-derived chiral bases

  摘要：

  Using a chiral base from a norephedrine-derived diamine, the enantioselective rearrangement of a mesocyclohexene oxide can be performed in 94% yield and with 94% enantioselectivity. The enantioselectivity is lower (86% ee) with the diastereoisomeric chiral base. In order to prepare the diastereoisomeric chiral base, a potentially useful way of converting norephedrine into norpseudophedrine was developed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00432-2
• 作为产物：
  描述：

  去甲麻黄碱 在 盐酸 、 偶氮二甲酸二异丙酯 、 四丁基碘化铵 、 sodium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 89.0h， 生成 (1S,2S)-1-phenyl-2-(pyrrolidin-1-yl)propan-1-ol
  参考文献：
  名称：

  Enantioselective rearrangement of a meso-cyclohexene oxide using norephedrine-derived chiral bases

  摘要：

  Using a chiral base from a norephedrine-derived diamine, the enantioselective rearrangement of a mesocyclohexene oxide can be performed in 94% yield and with 94% enantioselectivity. The enantioselectivity is lower (86% ee) with the diastereoisomeric chiral base. In order to prepare the diastereoisomeric chiral base, a potentially useful way of converting norephedrine into norpseudophedrine was developed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00432-2

文献信息

• Enantioselective and Diastereoselective Construction of Chiral Amino Alcohols by Iridium–f-Amphox-Catalyzed Asymmetric Hydrogenation via Dynamic Kinetic Resolution
  作者：Weilong Wu、Cai You、Congcong Yin、Yuanhua Liu、Xiu-Qin Dong、Xumu Zhang

  DOI：10.1021/acs.orglett.7b00844

  日期：2017.5.19

  The iridium–f-amphox-catalyzed asymmetric hydrogenation of racemic α-amino β-unfunctionalized ketones proceeds via a DKR (dynamic kinetic resolution) process for the construction of various chiral N,N-disubstituted α-amino β-unfunctionalized alcohols in quantitative yields with excellent enantioselectivities and diastereoselectivities (all products >99% ee and >99:1 dr, TON up to 100 000). Importantly

  外消旋α-氨基β-非官能化酮的铱-f-amphox催化的不对称氢化通过DKR（动态动力学拆分）过程进行，以定量产率构建各种手性N，N-二取代的α-氨基β-非官能化醇具有出色的对映选择性和非对映选择性（所有产品> 99％ee和> 99：1 dr，TON高达100000）。重要的是，这种采用DKR方法的催化不对称氢化为制备临床前抗肿瘤剂（S，S）-R116010的关键手性中间体提供了高效且强大的合成策略。
• Process for the synthesis of chiral propargylic alcohols
  申请人：Lonza Ltd

  公开号：EP2447247A1

  公开（公告）日：2012-05-02

  A process for the synthesis of chiral propargylic alcohols.

  手性丙炔醇的合成过程。
• Process for the synthesis of cyclic carbamates
  申请人：Lonza Ltd

  公开号：EP2447255A1

  公开（公告）日：2012-05-02

  The invention is directed to a process for the preparation of a cyclic carbamate starting with a chiral propargylic alcohol and/or a suitable salt thereof, which is reacted with a cyclisation agent selected from phosgene, diphosgene, triphosgene and mixtures thereof, and in that the reaction is carried out in the presence of an aqueous base, and a water-immiscible organic solvent, said organic solvent mainly comprising at least one compound selected from C2-5-alkyl C2-5-carboxylates and mixtures of at least one C2-5-alkyl C2-5-carboxylate with at least one C5-8-alkane. Another aspect of the invention is directed to a process for the synthesis of said cyclic carbamate starting described above, wherein also a process for the preparation of the chiral propargylic alcohol is provided.

  该发明涉及一种以手性丙炔醇和/或其适当盐为起始物，与从光气、二光气、三光气和它们的混合物中选择的环化试剂反应，且在水性碱和水不相溶的有机溶剂存在下进行反应的制备环氧羰基化合物的方法，所述有机溶剂主要包括至少一种选择自C2-5-烷基C2-5-羧酸酯和至少一种C5-8-烷烃的混合物的化合物。该发明的另一个方面涉及一种合成上述环氧羰基化合物的方法，其中还提供了一种制备手性丙炔醇的方法。
• PROCESS FOR THE SYNTHESIS OF CHIRAL PROPARGYLIC ALCOHOLS
  申请人：Brenner Meinrad

  公开号：US20130324763A1

  公开（公告）日：2013-12-05

  A process for the synthesis of chiral propargylic alcohols.

  合成手性丙炔基醇的过程。
• PROCESS FOR THE SYNTHESIS OF CYCLIC CARBAMATES
  申请人：Brenner Meinrad

  公开号：US20130211077A1

  公开（公告）日：2013-08-15

  The invention is directed to a process for the preparation of a cyclic carbamate starting with o-aminobenzyl alcohol and/or a suitable salt thereof, which is reacted with a cyclisation agent selected from phosgene, diphosgene, triphosgene and mixtures thereof, and in that the reaction carried out in the presence of an aqueous base, and a water-immiscible organic solvent, said organic solvent mainly comprising at least one compound selected from C 2-5 -alkyl C 2-5 -carboxylates and mixtures of at least one C 2-5 -alkyl C 2-5 -carboxylate with at least one C 5-8 -alkane.

  本发明涉及一种制备环状氨基甲酸酯的方法，其以o-氨基苄醇和/或适当的盐为起始物，与选择自光气、双光气、三光气和其混合物的环化试剂反应，并在水性碱和一种不溶于水的有机溶剂的存在下进行反应，所述有机溶剂主要包括至少一种选择自C2-5烷基C2-5羧酸酯和至少一种C5-8烷烃的混合物。