(R)-(-)-tert-butyl 2-oxo-1-phenylpropylcarbamate | 1277097-53-6

• 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)-(-)-tert-butyl 2-oxo-1-phenylpropylcarbamate
• 英文别名: tert-butyl N-[(1R)-2-oxo-1-phenylpropyl]carbamate
• CAS: 1277097-53-6
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: IYNDQTCBXIQQEJ-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(-)-tert-butyl 2-oxo-1-phenylpropylcarbamate 、 Ph3PCH3I 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.25h， 以75%的产率得到tert-butyl (S)-2-oxo-1-phenylpropylcarbamate
  参考文献：
  名称：

  Access to Enantiomerically Enriched cis-2,3-Disubstituted Azetidines via Diastereoselective Hydrozirconation

  摘要：

  An asymmetric variant of the hydrozirconation reaction has been established starting from Boc-protected chiral allylic amines. The resulting diastereoselectively formed N-functionalized organozirconiums can be considered as promising chirons. In this case, they have been transformed into enantiomerically enriched cis-2,3-disubstituted azetidines through a iodination/cyclization sequence.

  DOI：

  10.1021/ol200323r
• 作为产物：
  描述：

  Boc-D-苯甘氨酸 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 12.17h， 生成 (R)-(-)-tert-butyl 2-oxo-1-phenylpropylcarbamate
  参考文献：
  名称：

  Access to Enantiomerically Enriched cis-2,3-Disubstituted Azetidines via Diastereoselective Hydrozirconation

  摘要：

  An asymmetric variant of the hydrozirconation reaction has been established starting from Boc-protected chiral allylic amines. The resulting diastereoselectively formed N-functionalized organozirconiums can be considered as promising chirons. In this case, they have been transformed into enantiomerically enriched cis-2,3-disubstituted azetidines through a iodination/cyclization sequence.

  DOI：

  10.1021/ol200323r

文献信息

• Catalytic Asymmetric Cross-Aza-Benzoin Reactions of Aliphatic Aldehydes with<i>N</i>-Boc-Protected Imines
  作者：Daniel A. DiRocco、Tomislav Rovis

  DOI：10.1002/anie.201202442

  日期：2012.6.11

  Crossed: A catalyst system has been developed that allows the direct asymmetric coupling of aliphatic aldehydes and N‐Boc‐protected imines in a cross‐aza‐benzoin reaction (see scheme; Boc=tert‐butoxycarbonyl). The active catalyst is shown to react rapidly with the imine, however, the presence of an acid as co‐catalyst renders this process reversible and allows the regeneration of the catalyst.

  交叉：已开发出一种催化剂体系，允许脂肪醛和 N-Boc 保护的亚胺在交叉氮杂-安息香反应中直接不对称偶联（参见方案；Boc =叔丁氧基羰基）。活性催化剂显示出与亚胺快速反应，然而，作为助催化剂的酸的存在使该过程可逆并允许催化剂再生。
• Facile Access to Chiral Ketones through Metal-Free Oxidative CC Bond Cleavage of Aldehydes by O2
  作者：Bhoopendra Tiwari、Junmin Zhang、Yonggui Robin Chi

  DOI：10.1002/anie.201107473

  日期：2012.2.20

  the boot: The title reaction provides facile access to functionalized chiral ketones from chiral α,α′‐disubstituted aldehydes in the presence of molecular oxygen (see scheme). The CC bond‐cleavage approach offers an alternative or better method relative to the typical bond‐forming strategies used in synthesizing chiral ketones.

  为金属提供引导：通过标题反应，可以在分子氧存在的情况下轻松地从手性α，α'-二取代醛中获得官能化的手性酮（请参见方案）。与c  C键裂解方法提供替代的或更好的相对于在合成的手性酮所用的典型的键形成战略的一个方法。
• Enantioselective NH Insertion Reaction of α-Aryl α-Diazoketones: An Efficient Route to Chiral α-Aminoketones
  作者：Bin Xu、Shou-Fei Zhu、Xiao-Dong Zuo、Zhi-Chao Zhang、Qi-Lin Zhou

  DOI：10.1002/anie.201400236

  日期：2014.4.7

  A highly enantioselective NH insertion reaction of α‐diazoketones was developed by using cooperative catalysis by dirhodium(II) carboxylates and chiral spiro phosphoric acids. The insertion reaction provides a new access route to diverse chiral α‐aminoketones, which are versatile building blocks in organic synthesis, with fast reaction rates, good yields and high enantioselectivity under mild and

  羧酸二（II）盐和手性螺环磷酸的协同催化作用，开发了α-重氮酮的高对映选择性的NH插入反应。插入反应为各种手性α-氨基酮提供了一条新的途径，这些手性α-氨基酮是有机合成中的通用组成部分，在温和和中性条件下具有快速的反应速率，良好的收率和高对映选择性。
• [EN] METHOD OF PREPARING CHIRAL KETONES FROM ALDEHYDES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE CÉTONES CHIRALES À PARTIR D'ALDÉHYDES
  申请人：UNIV NANYANG TECH

  公开号：WO2013095301A1

  公开（公告）日：2013-06-27

  Present invention relates to a method of preparing a chiral α- or β-substituted ketone from the corresponding β- or γ-substituted aldehyde, wherein the ketone has formula (I), (III) or (V), and the corresponding aldehyde has formula (II), (IV) or (VI), respectively, the method comprising reacting the aldehyde of formula (II), (IV) or (VI) in the presence of an amine, oxygen and an organic solvent, wherein the reaction is carried out in the absence of a metal-based catalyst or a metal-based oxidant, wherein: R is H, a substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C15 alkenyl, substituted or unsubstituted C2-C15 alkynyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C3-C15 cycloalkenyl, substituted or unsubstituted C3-C15 heterocycloalkyl, substituted or unsubstituted C3-C15 heterocycloalkenyl, substituted or unsubstituted C6-C15 aryl, or substituted or unsubstituted C6-C15 heteroaryl; and R' is H, a substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C15 alkenyl, substituted or unsubstituted C2-C15 alkynyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C3-C15 cycloalkenyl, substituted or unsubstituted C3-C15 heterocycloalkyl, substituted or unsubstituted C3-C15 heterocycloalkenyl, substituted or unsubstituted C6-C15 aryl, or substituted or unsubstituted C6-C15 heteroaryl.

  本发明涉及一种从相应的β-或γ-取代醛制备手性α-或β-取代酮的方法，其中酮具有式(I)、(III)或(V)，相应的醛具有式(II)、(IV)或(VI)，该方法包括在胺、氧和有机溶剂存在下反应式(II)、(IV)或(VI)的醛，其中反应在无金属催化剂或金属氧化剂存在下进行，其中：R为H、取代或未取代的C1-C10烷基、取代或未取代的C2-C15烯基、取代或未取代的C2-C15炔基、取代或未取代的C3-C15环烷基、取代或未取代的C3-C15环烯基、取代或未取代的C3-C15杂环烷基、取代或未取代的C3-C15杂环烯基、取代或未取代的C6-C15芳基或取代或未取代的C6-C15杂芳基；R'为H、取代或未取代的C1-C10烷基、取代或未取代的C2-C15烯基、取代或未取代的C2-C15炔基、取代或未取代的C3-C15环烷基、取代或未取代的C3-C15环烯基、取代或未取代的C3-C15杂环烷基、取代或未取代的C3-C15杂环烯基、取代或未取代的C6-C15芳基或取代或未取代的C6-C15杂芳基。
• 5,5-FUSED ARYLENE OR HETEROARYLENE HEPATITIS C VIRUS INHIBITORS
  申请人：Idenix Pharmaceuticals LLC

  公开号：EP2513113B1

  公开（公告）日：2018-08-01