(+/-)-phenylglycinol benzyl ether | 127001-22-3

• 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: (+/-)-phenylglycinol benzyl ether
• 英文别名: 2-(benzyloxy)-1-phenylethylamine；2-(Benzyloxy)-1-phenylethan-1-amine；1-phenyl-2-phenylmethoxyethanamine
• CAS: 127001-22-3
• 化学式: C₁₅H₁₇NO
• mdl: MFCD09729442
• 分子量: 227.306
• InChiKey: ZMNPFYANVKDFQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-phenylglycinol benzyl ether 在 sodium hydroxide 、 sodium sulfate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 N-<2'-(phenylmethoxy)-1'-phenylethyl>-N-hydroxy-1-phenylethanamine
  参考文献：
  名称：

  Enantioselective synthesis of primary amines via Grignard additions to stereogenic N-(.alpha.-phenyl-.beta.-(benzyloxy)ethyl)nitrones

  摘要：

  DOI：

  10.1021/jo00298a019
• 作为产物：
  描述：

  L-苯甘氨酸 在 sodium tetrahydroborate 、 氯化亚砜 、 potassium hydride 作用下， 以 乙醇 为溶剂， 反应 32.5h， 生成 (+/-)-phenylglycinol benzyl ether
  参考文献：
  名称：

  Enantioselective synthesis of primary amines via Grignard additions to stereogenic N-(.alpha.-phenyl-.beta.-(benzyloxy)ethyl)nitrones

  摘要：

  DOI：

  10.1021/jo00298a019

文献信息

• Stereoselective synthesis of β-lactams by condensation of titanium enolates of 2-pyridyl thioesters with imines bearing a chiral auxiliary
  作者：Rita Annunziata、Maurizio Benaglia、Mauro Cinquini、Franco Cozzi、Laura Raimondi

  DOI：10.1016/s0040-4020(01)85521-6

  日期：——

  tested as chiral auxiliaries in the stereoselective synthesis of β-lactams by condensation of the titanium enolates of 2-pyridyl thioesters with chiral imines. The amines were selected among the following classes of compounds: benzylic amines, β-aminoalcohols, β-heterosubstituted α-aminoesters. Inexpensive and available in both enantiomeric forms α-methylbenzylamine was identified as the chiral auxiliary

  通过2-吡啶基硫酯的烯醇钛与手性亚胺的缩合，β-内酰胺的立体选择性合成中已测试了几种胺作为手性助剂。胺选自以下化合物：苄基胺，β-氨基醇，β-杂取代的α-氨基酯。廉价且可以两种对映体形式获得的α-甲基苄胺被鉴定为手性助剂，通常结合了良好的反应性和令人满意的立体控制水平。为了说明该方法的潜力，制备了肾素抑制剂成分的前体。介绍了立体化学结果的初步合理化。
• Synthesis and Evaluation of a Broad Range of New Chiral (Aminoalkyl)phosphane Ligands for Asymmetric Hydrogen-Transfer Reduction of Prochiral Ketones
  作者：Matthieu Léautey、Philippe Jubault、Xavier Pannecoucke、Jean-Charles Quirion

  DOI：10.1002/ejoc.200300131

  日期：2003.10

  Twenty new chiral (aminoalkyl)phosphane ligands have been prepared from four enantiomerically pure advanced chiral compounds. We describe their use for asymmetric hydrogen-transfer reduction of three prochiral ketones. Enantioselectivities up to 90% were obtained. We investigated the influence on the enantioselectivity of each part of these new (aminoalkyl)phosphane ligands. (© Wiley-VCH Verlag GmbH

  已经从四种对映体纯的高级手性化合物制备了 20 种新的手性（氨基烷基）膦配体。我们描述了它们在三个前手性酮的不对称氢转移还原中的用途。获得了高达 90% 的对映选择性。我们研究了这些新（氨基烷基）膦配体的每一部分对对映选择性的影响。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Design, synthesis, and evaluation of cyclic amide/imide-bearing hydroxamic acid derivatives as class-selective histone deacetylase (HDAC) inhibitors
  作者：Chihiro Shinji、Satoko Maeda、Keisuke Imai、Minoru Yoshida、Yuichi Hashimoto、Hiroyuki Miyachi

  DOI：10.1016/j.bmc.2006.07.008

  日期：2006.11

  A series of hydroxamic acid derivatives bearing a cyclic amide/imide group as a linker and/or cap structure, prepared during our structural development studies based on thalidomide, showed class-selective potent histone deacetylase (HDAC)-inhibitory activity. Structure-activity relationship studies indicated that the steric character of the substituent introduced at the cyclic amide/imide nitrogen

  在我们根据沙利度胺进行的结构开发研究中制备的一系列带有环状酰胺/酰亚胺基团作为连接基和/或帽结构的异羟肟酸衍生物显示出对类组有效的组蛋白脱乙酰基酶（HDAC）的抑制活性。结构-活性关系研究表明，在环状酰胺/酰亚胺氮原子上引入的取代基的空间特征，酰胺/酰亚胺羰基的存在，异羟肟酸的结构，连接基团的形状以及它们之间的距离结合锌的异羟肟酸基团和帽结构对于抑制HDAC的活性和类别选择性都很重要。具有代表性的化合物（30w）显示出强效的p21启动子活性，与曲古抑菌素A（TSA）相当，
• Diastereoselective addition of terminal alkynes to chiral nitrones: asymmetric synthesis of propargylic N-hydroxylamines
  作者：Samir K. Patel、Sandrine Py、Shashi U. Pandya、Pierre Y. Chavant、Yannick Vallée

  DOI：10.1016/s0957-4166(03)00032-6

  日期：2003.3

  1,3-Asymmetric induction in the Et2Zn-catalyzed addition of terminal alkynes was studied with nitrones bearing a chiral auxiliary on their nitrogen atom. The obtained propargylic N-hydroxylamines were generally isolated in good yields and with satisfactory to excellent diastereoselectivities.

  研究了在Et 2 Zn催化的末端炔烃加成反应中的1,3-不对称诱导作用，其中硝酮在氮原子上带有手性助剂。所获得的炔丙基N-羟基胺通常以高收率分离并且具有令人满意的至优异的非对映选择性。
• Stereoselective synthesis of β-lactams by condensation of titanium enolates of 2-pyridylthioesters with imines bearing a chiral auxiliary
  作者：Rita Annunziata、Maurizio Benaglia、Mauro Cinquini、Franco Cozzi、Laura Raimondi

  DOI：10.1016/s0040-4039(00)91831-8

  日期：1993.10

  Addition of the titanium enolates of 2-pyridylthioesters to imines featuring easily removable chiral auxiliaries affords β-lactams in a highly stereoselective fashion.

  在具有易于除去的手性助剂的亚胺中加成2-吡啶硫基钛酸酯的烯醇钛化物，可以以高度立体选择性的方式提供β-内酰胺。