(R)-azetidin-2-yl(diphenyl)methanol | 144062-04-4

• 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: (R)-azetidin-2-yl(diphenyl)methanol
• 英文别名: [(2R)-azetidin-2-yl]-diphenylmethanol
• CAS: 144062-04-4
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: MIWZUUDZNFGLRT-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  溴甲苯 、 (R)-azetidin-2-yl(diphenyl)methanol 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以54.5%的产率得到(R)-(1-benzylazetidin-2-yl)diphenylmethanol
  参考文献：
  名称：

  Ligand-accelerated Enantioselective Propargylation of Aldehydes via Allenylzinc Reagents

  摘要：

  An enantioselective propargylation of aldehydes using an allenylzinc reagent generated in situ via a zinc-iodine exchange reaction is described. The enantioselectivity is controlled by addition of a catalytic amount of readily accessible and highly tunable amino alcohol ligand L13. A wide range of aldehydes can be propargylated to afford valuable and versatile homopropargyl alcohols in good to excellent yields with high levels of enantiopurity.

  DOI：

  10.1021/ol200043n
• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.08h， 以75%的产率得到(R)-azetidin-2-yl(diphenyl)methanol
  参考文献：
  名称：

  Enantioselective catalytic reductions of ketones with new four membered oxazaborolidines: Application to (S)-tetramisole

  摘要：

  Enantioselective catalytic reduction of ketones with both the enantiomers of new four membered oxazaborolidines is described.

  DOI：

  10.1016/s0957-4166(00)82184-9
• 作为试剂：
  描述：

  alpha-氯乙酰苯 在 硼烷 、 (R)-azetidin-2-yl(diphenyl)methanol 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-(+)-2-氯-1-苯乙醇 、 (R)-(-)-2-氯-1-苯乙醇
  参考文献：
  名称：

  Enantioselective catalytic reductions of ketones with new four membered oxazaborolidines: Application to (S)-tetramisole

  摘要：

  Enantioselective catalytic reduction of ketones with both the enantiomers of new four membered oxazaborolidines is described.

  DOI：

  10.1016/s0957-4166(00)82184-9

文献信息

• CATALYST FOR ASYMMETRIC HYDROGENATION
  申请人：MAEDA Hironori

  公开号：US20100324338A1

  公开（公告）日：2010-12-23

  This invention aims at providing a catalyst for producing an optically active aldehyde or an optically active ketone, which is an optically active carbonyl compound, by carrying out selective asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, particularly a catalyst which is insoluble in a reaction mixture for obtaining optically active citronellal which is useful as a flavor or fragrance, by carrying out selective asymmetric hydrogenation of citral, geranial or neral; and a method for producing a corresponding optically active carbonyl compound. The invention relates to a catalyst for asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, which comprises a powder of at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table, or a metal-supported substance in which at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table is supported on a support, an optically active cyclic nitrogen-containing compound and an acid.

  这项发明旨在通过对α，β-不饱和羰基化合物进行选择性不对称加氢，特别是通过对柠檬醛、香叶醛或柠檬醛进行选择性不对称加氢，从而提供用作香料或香精的有用的光学活性香茅醛的催化剂，该香茅醛是一种光学活性羰基化合物；以及生产相应的光学活性羰基化合物的方法。该发明涉及一种用于不对称加氢α，β-不饱和羰基化合物的催化剂，其包括来自周期表第8至第10族金属中至少一种金属的粉末，或者至少一种来自周期表第8至第10族金属的金属负载物质，该金属负载在一种支撑物上，还包括光学活性的含氮环化合物和酸。
• Enantioselective Friedel–Crafts Alkylation of Pyrrole with Chalcones Catalyzed by a Dinuclear Zinc Catalyst
  作者：Yuan-Zhao Hua、Xing-Wang Han、Xiao-Chao Yang、Xixi Song、Min-Can Wang、Jun-Biao Chang

  DOI：10.1021/jo5023712

  日期：2014.12.5

  A highly enantioselective Friedel–Crafts (F–C) alkylation of pyrrole with a wide range of simple nonchelating chalcone derivatives catalyzed by a chiral (Zn2EtL)n (L = (S,S)-1) complex has been developed. The catalyst (Zn2EtL)n complex was prepared in situ by reacting the chiral ligand (S,S)-1 with 2 equiv of diethylzinc. A series of β-pyrrole-substituted dihydrochalcones were usually formed mostly

  具有宽范围由手性（锌催化的简单nonchelating查耳酮衍生物的吡咯的对映体选择性高的Friedel-Crafts（F-C）烷基化2 ETL）Ñ（L =（S，S） - 1）复合物已被开发出来。通过使手性配体（S，S）-1与2当量的二乙基锌反应原位制备催化剂（Zn 2 EtL）n配合物。通过在温和条件下使用15 mol％的催化剂，通常以极好的收率（最高达99％）和出色的对映选择性（最高达99％对映体过量（ee））形成一系列β-吡咯取代的二氢查耳酮。产品的绝对立体化学确定为X射线晶体学分析13g为S构型。同时，观察到微弱的负非线性效应。根据实验结果和以前的报道，提出了一种可能的机制来解释不对称感应的起源。
• Addition of the Lithium Anion of Diphenylmethanol Methyl/Methoxymethyl Ether to Nonracemic Sulfinimines: Two-Step Asymmetric Synthesis of Diphenylprolinol Methyl Ether and Chiral (Diphenylmethoxymethyl)amines
  作者：Arava Amaranadha Reddy、Kavirayani R. Prasad

  DOI：10.1021/acs.joc.8b01381

  日期：2018.9.21

  from diphenylmethanol methyl and methoxymethyl ether to nonracemic sulfinimines afforded the corresponding addition products in excellent diastereoselctivity and yields. Deprotection of the MOM as well as sulfinyl groups rendered the enantiopure (diphenylhydroxymethyl)amines in excellent yields. The procedure was applied for a two-step synthesis of diphenylprolinol, a privileged ligand in asymmetric

  由二苯基甲醇甲基和甲氧基甲基醚产生的锂阴离子加到非外消旋亚氨基亚胺上，以优异的非对映选择性和收率提供了相应的加成产物。MOM以及亚磺酰基的脱保护使得对映体纯的（二苯基羟甲基）胺具有极好的收率。该程序适用于两步合成二苯基脯氨醇，这是不对称催化中的优先配体。
• Verfahren zur stereoselektiven Reduktion von 17-Oxo-Steroiden
  申请人：Jenapharm GmbH & Co. KG

  公开号：EP0713880B1

  公开（公告）日：1998-06-10
• US5830468A
  申请人：——

  公开号：US5830468A

  公开（公告）日：1998-11-03