N-phthaloyl-L-valinal | 55707-37-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-phthaloyl-L-valinal
• 英文别名: Pht-Val-H；N-((S)-1-formyl-2-methyl-propyl)-phthalimide；N-((S)-1-Formyl-2-methyl-propyl)-phthalimid；(2S)-2-(1,3-dioxoisoindol-2-yl)-3-methylbutanal
• CAS: 55707-37-4
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: BERZBIGQXSVCBJ-LLVKDONJSA-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：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-phthaloyl-L-valinal 在 indium 、 硫酸 、 三乙胺 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 89.0h， 生成 2-[(S)-2-Methyl-1-((S)-5-oxo-4-phenylsulfanylmethyl-tetrahydro-furan-2-yl)-propyl]-isoindole-1,3-dione
  参考文献：
  名称：

  Indium-Induced Addition of Bromomethylacrylates to Phthaloyl-Protected Amino Aldehydes

  摘要：

  研究了在水溶剂中，邻苯二甲酰保护的α-氨基酸醛1-4与甲基2-（溴甲基）丙烯酸酯的铟介导反应。得到了同烯丙醇5-8，产率为72-89%，反式异构体为主要立体异构体（dr 45:55-18:82）。酸催化酯化（H2SO4在Et2O中）生成α-亚甲基γ-丁内酯9,10，产率范围为88至99%。氰化物和噻酚的共轭加成产物与加成到氨基甲酸酯保护的底物相比，选择性有所提高。在共轭加成铜试剂时，邻苯二甲酰羰基对中间体烯醇的捕获作用发生，导致了四环化合物11的生成，产率为57%。所有立体异构体的构型可以通过三次X射线晶体学分析和核磁共振波谱确定。

  DOI：

  10.1055/s-2002-28503
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 Pd-BaSO₄ 、 xylene 作用下， 生成 N-phthaloyl-L-valinal
  参考文献：
  名称：

  Optically Active Amino Aldehydes. II. Preparation of Cyclic Acetals of Quaternary Amino Aldehydes; Contribution to the Knowledge of the Stereospecificity of Muscarinic Activity¹

  摘要：

  DOI：

  10.1021/jo01107a026

文献信息

• Diastereoselective catalytic asymmetric nitroaldol reaction utilizing rare earth-Li-(R)-BINOL complex. A highly efficient synthesis of norstatine
  作者：Hiroaki Sasai、Won-Sup Kim、Takeyuki Suzuki、Masakatsu Shibasaki、Masaru Mitsuda、Junzo Hasegawa、Takehisa Ohashi

  DOI：10.1016/0040-4039(94)88093-x

  日期：1994.8

  Rare earth-Li-BINOL complexes were used to catalyze nitroaldol reactions of optically active α-amino-aldehydes with nitromethane in a highly diastereoselective manner. A typical adduct, (2S, 3S)-3-phthaloylamino-2-hydroxy-1-nitro-4-phenylbutane was conveniently converted to (2S, 3S)-3-amino-2-hydroxy-4-phenylbutanoic acid (erythro-AHPA ; phenylnorstatine), a component of the HIV protease inhibitor

  稀土-Li-BINOL络合物用于以高度非对映选择性的方式催化旋光性α-氨基醛与硝基甲烷的硝基羟醛反应。典型的加合物（2 S，3 S）-3-邻苯二甲酰基氨基-2-羟基-1-硝基-4-苯基丁烷可方便地转化为（2 S，3 S）-3-氨基-2-羟基-4-苯基丁酸酸（赤型-AHPA；苯基去甲他汀），是HIV蛋白酶抑制剂KNI-227和KNI-272的成分。
• Tetraallylstannane and Weinreb amides: a simple ‘green’ route to N-protected homoallylic alcohols and allyl ketones
  作者：Adam McCluskey、James Garner、David J Young、Shirley Caballero

  DOI：10.1016/s0040-4039(00)01408-8

  日期：2000.10

  We have explored the addition of tetraallylstannane (7) to a variety of N-protected Weinreb amides (N-phthalimido and N-benzyl). Reactions were conducted in methanol and the ionic liquid, butyl-methylimidazole tetrafluoroborate (bmim[BF4]), yields of the corresponding N-protected allylketones were moderate to good. Allylation of the corresponding aminoaldehydes gave excellent yields of homoallylic alcohols (68-94%) and moderate to good diastereoselectivities (50-86%). (C) 2000 Published by Elsevier Science Ltd.
• Indium-Induced Addition of Bromomethylacrylates to Phthaloyl-Protected Amino Aldehydes
  作者：Steffen Steurer、Joachim Podlech

  DOI：10.1055/s-2002-28503

  日期：——

  The indium-mediated reaction of phthaloyl-protected α-amino aldehydes 1-4 with methyl 2-(bromomethyl)acrylate in aqueous solvents was investigated. The homoallyl alcohols 5-8 were formed in 72-89% yields, the anti-isomers being the major diastereoisomers (dr 45:55-18:82). Acid-catalyzed esterification (H2SO4 in Et2O) led to α-methylene γ-butyrolactones 9,10 with yields ranging from 88 to 99%. Conjugate addition of cyanide and thiophenolate led to the addition products with improved selectivities compared with additions to carbamate-protected substrates. During the conjugate addition of a cuprate, a trapping of the intermediate enolate by a phthaloyl carbonyl group occurred, leading to tetracycle 11 in 57% yield. The configuration of all diastereo­isomers could be established by three X-ray crystallographic analyses and by NMR spectroscopy.

  研究了在水溶剂中，邻苯二甲酰保护的α-氨基酸醛1-4与甲基2-（溴甲基）丙烯酸酯的铟介导反应。得到了同烯丙醇5-8，产率为72-89%，反式异构体为主要立体异构体（dr 45:55-18:82）。酸催化酯化（H2SO4在Et2O中）生成α-亚甲基γ-丁内酯9,10，产率范围为88至99%。氰化物和噻酚的共轭加成产物与加成到氨基甲酸酯保护的底物相比，选择性有所提高。在共轭加成铜试剂时，邻苯二甲酰羰基对中间体烯醇的捕获作用发生，导致了四环化合物11的生成，产率为57%。所有立体异构体的构型可以通过三次X射线晶体学分析和核磁共振波谱确定。
• Optically Active Amino Aldehydes. II. Preparation of Cyclic Acetals of Quaternary Amino Aldehydes; Contribution to the Knowledge of the Stereospecificity of Muscarinic Activity¹
  作者：K. BALENOVIć、N. BREGANT、T. GALIJAN、Z. ŠTEFANAC、V. ŠKARIć

  DOI：10.1021/jo01107a026

  日期：1956.1