(R)-1-azido-3-phenylpropan-2-ol | 112009-62-8

• 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)-1-azido-3-phenylpropan-2-ol
• 英文别名: (R)-1-Azido-3-phenyl-2-propanol；(2R)-1-azido-3-phenylpropan-2-ol
• CAS: 112009-62-8
• 化学式: C₉H₁₁N₃O
• mdl: MFCD28505824
• 分子量: 177.206
• InChiKey: RDZHIJATXQDZPO-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  34.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-1-azido-3-phenylpropan-2-ol 生成 [(2R)-1-azido-3-phenylpropan-2-yl] tert-butyl carbonate
  参考文献：
  名称：

  TAKANO, SEHJITI;OGASAVARA, KUNIO;SEHKIGUTI, JOSIKO;KASAI, NAOYA;SAKAGUTI,+

  摘要：

  DOI：
• 作为产物：
  描述：

  D-苯基乳酸甲酯 在 Wang resin trichloroacetimidate 、 叠氮磷酸二苯酯 、 二异丁基氢化铝 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 生成 (R)-1-azido-3-phenylpropan-2-ol
  参考文献：
  名称：

  用聚合物结合的对烷氧基苄基醚探索功能和分子多样性—有用的有机反应的范围和应用

  摘要：

  Alcohols immobilized as p-alkoxybenzyl ethers on Wang resins have been subjected to a variety of chemical transformations based on existing functionality (enolate chemistry, carbonyl group reactivity, Mitsunobu inversion, ozonolysis, Heck reactions, etc.), in an effort to test the suitability of this novel resin-bound ether linkage. The modified substrate was released from the resin by mild acid treatment. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10685-2

文献信息

• Intramolecular reductive amination strategy to the synthesis of (R)-N-Boc-2-hydroxymethylmorpholine, N-(3,4-dichlorobenzyl)(R)-2-hydroxymethylmorpholine, and (R)-2-benzylmorpholine
  作者：Rajiv T. Sawant、Suresh B. Waghmode

  DOI：10.1016/j.tet.2010.01.047

  日期：2010.3

  (R)-N-Boc-2-hydroxymethylmorpholine, N-(3,4-dichlorobenzyl)(R)-2-hydroxymethylmorpholine, and (R)-benzylmorpholine has been achieved by employing proline-catalyzed asymmetric α-aminooxylation of aldehyde and palladium-catalyzed intramolecular reductive amination of azido aldehyde as the key steps.

  通过使用脯氨酸催化，已经实现了（R）-N -Boc-2-羟甲基吗啉，N-（3,4-二氯苄基）（R）-2-羟甲基吗啉和（R）-苄基吗啉的简明高产对映选择性合成。醛的不对称α-氨氧基化和钯催化的叠氮基醛的分子内还原胺化是关键步骤。
• Expanding the Scope of Enantioselective Halohydrin Dehalogenases – Group B
  作者：Emina Mehić、Lucija Hok、Qian Wang、Irena Dokli、Marina Svetec Miklenić、Zvjezdana Findrik Blažević、Lixia Tang、Robert Vianello、Maja Majerić Elenkov

  DOI：10.1002/adsc.202200342

  日期：2022.8.2

  (HHDHs) possess an unnatural activity of introducing functionalities such as N3, CN, NO2 etc., into a molecule through the ring-opening reaction of epoxides. The enantioselectivity of HHDHs is substrate-dependent and not always high enough for synthetic applications. B-group of HHDHs has been neglected in the past, due to observed low enantioselectivity based on performance on a relatively limited number

  卤代醇脱卤酶(HHDHs)具有通过环氧化物的开环反应将诸如N 3、CN、NO 2等官能团引入分子中的非天然活性。HHDH 的对映选择性取决于底物，对于合成应用而言并不总是足够高。由于在相对有限数量的底物上的性能观察到的低对映选择性，HHDH 的 B 组过去一直被忽视。广泛筛选来自分枝杆菌的 HheB2 底物。来自棒状杆菌属的 GP1 和 HheB 。进行了 N-1074。发现了几个高度对映选择性的反应（E>200)，与 HheB2 相比，HheB 对更大的底物面板显示出更高的对映选择性和活性。酶 HheB 和 HheB2 高度同源；它们仅相差 4 个残基。通过使用定点诱变，发现与 HheB2 相比，残基 120 和 125 是 HheB 对映选择性更高的原因。计算分析支持实验并提供证据表明 HheB 酶内反应的动力学和热力学参数对于确定观察到的对映选择性至关重要。如本工作所示，由于显着的活性和对映选择性，B
• Azidolysis of epoxides catalysed by the halohydrin dehalogenase from Arthrobacter sp. AD2 and a mutant with enhanced enantioselectivity: an (S)-selective HHDH
  作者：Ana Mikleušević、Ines Primožič、Tomica Hrenar、Branka Salopek-Sondi、Lixia Tang、Maja Majerić Elenkov

  DOI：10.1016/j.tetasy.2016.08.003

  日期：2016.10

  Halohydrin dehalogenase from Arthrobacter sp. AD2 catalysed azidolysis of epoxides with high regioselectivity and low to moderate (S)-enantioselectivity (E = 1-16). Mutation of the asparagine 178 to alanine (N178A) showed increased enantioselectivity towards styrene oxide derivatives and glycidyl ethers. Conversion of aromatic epoxides was catalysed by HheA-N178A with complete enantioselectivity, however the regioselectivity was reduced. As a result of the enzyme-catalysed reaction, enantiomerically pure (S)-beta-azido alcohols and (R)-alpha-azido alcohols (ee >= 99%) were obtained. (C) 2016 Published by Elsevier Ltd.
• Practical synthesis of (R)-γ-amino-β-hydroxybutanoic acid (GABOB) from (R)-epichlorohydrin
  作者：Seiichi Takano、Masashi Yanase、Yoshinori Sekiguchi、Kunio Ogasawara

  DOI：10.1016/s0040-4039(00)95420-0

  日期：1987.1
• TAKANO SEIICHI; YANASE MASASHI; SEKIGUCHI YOSHINORI; OGASAWARA KUNIO, TETRAHEDRON LETT., 28,(1987) N 16, 1783-1784
  作者：TAKANO SEIICHI、 YANASE MASASHI、 SEKIGUCHI YOSHINORI、 OGASAWARA KUNIO

  DOI：——

  日期：——