5-hydroxyimino-5-phenylpentanoic acid methyl ester | 934520-52-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-hydroxyimino-5-phenylpentanoic acid methyl ester
• 英文别名: methyl 5-hydroxyimino-5-phenylpentanoate；Methyl 5-hydroxyimino-5-phenylpentanoate
• CAS: 934520-52-2
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: JMCQUGNTGWUYMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-hydroxyimino-5-phenylpentanoic acid methyl ester 在 乙酸酐 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 0.28h， 以61%的产率得到甲基5-苯基-3,4-二氢-2H-吡咯-2-甲酸基酯
  参考文献：
  名称：

  Novel Intramolecular Reactivity of Oximes:  Synthesis of Cyclic and Spiro-Fused Imines

  摘要：

  Under conventional heat (135-145 degrees C) or microwave irradiation and 1 equiv of acetic anhydride, ortho-substituted aryl-oximes undergo a novel sp(3) C-H activated cyclization to produce the corresponding isoindoles, and aliphatic oximes afford the corresponding dihydropyrroles. The cyclization occurs with various substrates in good yield (46-82%) leading to unique spiro-fused and cyclic imines. An initial mechanistic investigation suggests the reaction occurs via a nitrenium or vinyl nitrene intermediate.

  DOI：

  10.1021/ol0630043
• 作为产物：
  描述：

  4-苯甲酰基丁酸甲酯 在 盐酸羟胺 、 sodium acetate 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 以81%的产率得到5-hydroxyimino-5-phenylpentanoic acid methyl ester
  参考文献：
  名称：

  通过 5-乙酰氨基戊-4-烯酸衍生物的不对称氢化制备 δ-氨基酸的立体控制方法

  摘要：

  5-乙酰氨基-5-苯基戊-4-烯酸甲酯或N,N-二甲基酰胺中C=C键的不对称氢化由铑配合物与手性双膦配体催化（催化剂的1 mol%，20 atm. H2, MeOH, 50 °C) 得到相应的饱和衍生物，对映选择性高达 40%??。

  DOI：

  10.1007/s11172-010-0263-4

文献信息

• Stereocontrolled approach to δ-amino acids by asymmetric hydrogenation of 5-acetylaminopent-4-enoic acid derivatives
  作者：E. V. Starodubtseva、O. V. Turova、O. M. Antipova、M. G. Vinogradov、Zh. R. Sagirova、O. R. Malyshev、M. I. Struchkova

  DOI：10.1007/s11172-010-0263-4

  日期：2010.7

  Asymmetric hydrogenation of the C=C bond in 5-acetylamino-5-phenylpent-4-enoic acid methyl ester or N,N-dimethylamide catalyzed by rhodium complexes with chiral bisphosphine ligands (1 mol.% of the catalyst, 20 atm. of H2, MeOH, 50 °C) gives the corresponding saturated derivatives with enantioselectivity up to 40% ??.

  5-乙酰氨基-5-苯基戊-4-烯酸甲酯或N,N-二甲基酰胺中C=C键的不对称氢化由铑配合物与手性双膦配体催化（催化剂的1 mol%，20 atm. H2, MeOH, 50 °C) 得到相应的饱和衍生物，对映选择性高达 40%??。
• The design and synthesis of a novel quinolizidine template for potent opioid and opioid receptor-like (ORL1, NOP) receptor ligands
  作者：Ling Jong、Nurulain Zaveri、Lawrence Toll

  DOI：10.1016/j.bmcl.2003.09.068

  日期：2004.1

  A new class of high affinity opioid and opioid receptor-like receptor (ORL1 receptor, NOP receptor) ligands has been designed by conformational restriction of piperidine-based NOP receptor ligands, resulting in a novel quinolizidine scaffold. Different modifications of the pendant functional groups on the scaffold provide differential activities at the opioid and NOP receptors. While the conformational rigidity will provide an improved understanding of the NOP and opioid receptor binding pockets, these compounds also provide a new template for the design of novel opiate and NOP ligands. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of Air- and Moisture-Stable, Storable Chiral Oxorhenium Complexes and Their Application as Catalysts for the Enantioselective Imine Reduction
  作者：Braja Gopal Das、Rajender Nallagonda、Dhananjay Dey、Prasanta Ghorai

  DOI：10.1002/chem.201501914

  日期：2015.9.1

  salicyloxazoline based oxorhenium(V) complexes have been synthesized and their catalytic application for the asymmetric reduction of ketimines using hydrosilane as hydride source is disclosed. A broad substrate scope, high yields, and excellent enantioselectivities (up to 99 %) are attained. Furthermore, the syntheses of enantiopure α‐amino esters, γ‐ and δ‐lactams, and isoindolinones have also been carried

  合成了空气/水分稳定，晶体和可储存的手性水杨基恶唑啉基氧化（V）配合物，并公开了其在氢化硅烷作为氢化物源的情况下催化不对称还原酮亚胺的催化应用。获得了广泛的底物范围，高收率和出色的对映选择性（最高99％）。此外，对映体纯α-氨基酯，γ-和δ-内酰胺以及异吲哚啉酮的合成也已使用该方法进行。最后，该方法已应用于具有药物相关性的合成靶标，例如R -（+）-沙丁胺碱和R -（+）-crispine A.
• Novel Intramolecular Reactivity of Oximes:  Synthesis of Cyclic and Spiro-Fused Imines
  作者：Cécile G. Savarin、Christiane Grisé,、Jerry A. Murry、Robert A. Reamer、David L. Hughes

  DOI：10.1021/ol0630043

  日期：2007.3.1

  Under conventional heat (135-145 degrees C) or microwave irradiation and 1 equiv of acetic anhydride, ortho-substituted aryl-oximes undergo a novel sp(3) C-H activated cyclization to produce the corresponding isoindoles, and aliphatic oximes afford the corresponding dihydropyrroles. The cyclization occurs with various substrates in good yield (46-82%) leading to unique spiro-fused and cyclic imines. An initial mechanistic investigation suggests the reaction occurs via a nitrenium or vinyl nitrene intermediate.