N-cinnamoyl-(L)-proline | 107173-65-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-cinnamoyl-(L)-proline
• 英文别名: N-(trans-cinnamoyl)-l-proline；(2S)-1-[(E)-3-phenylprop-2-enoyl]pyrrolidine-2-carboxylic acid
• CAS: 107173-65-9
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: WSBOYOYQOJYXMU-BCPZQOPPSA-N

物化性质

• 熔点：
  178.5-180 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
• 沸点：
  504.2±49.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-cinnamoyl-(L)-proline 在 polyaniline supported cobalt(II) salen lithium hydroxide 、 水 、 氧气 、 sodium acetate 、 三乙胺 、 异丁醛 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 、 乙腈 为溶剂， 反应 21.01h， 生成 ((S)-4-Methyl-2-{[(S)-1-((2R,3S)-3-phenyl-oxiranecarbonyl)-pyrrolidine-2-carbonyl]-amino}-pentanoylamino)-acetic acid allyl ester
  参考文献：
  名称：

  Reverse Turn Induced π-Facial Selectivity during Polyaniline-Supported Cobalt(II) Salen Catalyzed Aerobic Epoxidation of N-Cinnamoyl l-Proline Derived Peptides

  摘要：

  A novel chemo- and diastereoselective aerobic epoxidation of the N-cinnamoyl peptides catalyzed by polyaniline-supported cobalt(II) salen (PASCOS) is described. The N-cinnamoyl proline derived peptides 1 show a high pi-facial selectivity during these epoxidations. The origin of this diastereo-selectivity in 1 has been attributed to (i) the propensity of the N-cinnamoyl proline amide to exist predominantly as trans rotamer in CDCl3, DMSO-d(6), and CH3CN medium and (ii) existence of these peptides as organized structures (gamma- and beta-turns) due to the presence of intramolecular hydrogen bonds. An extensive solution NMR and MD simulation study on 1d and 1f indicates that the origin of the high pi-facial selectivity is due to the well-defined gamma- and beta-turns which result in the hindrance of one face of the cinnamoyl double bond in the transition state of the epoxidation reaction.

  DOI：

  10.1021/jo020352j
• 作为产物：
  描述：

  3-苯基-2-丙烯酰氯 、 L-脯氨酸 在 potassium phosphate 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 以78%的产率得到N-cinnamoyl-(L)-proline
  参考文献：
  名称：

  一种新型有机 NLO 晶体的合成、物理化学和量子化学研究：肉桂酰脯氨酸

  摘要：

  摘要 采用缓慢蒸发法合成肉桂酰脯氨酸并从溶液中生长晶体。该晶体属于非中心对称空间群P31的三角晶系。比较了从单晶 X 射线数据计算出的几何形状和实验几何形状。使用 Hirshfeld 表面分析研究分子间相互作用，使用分子中的原子 (AIM) 计算其真实空间函数，使用非共价相互作用分析可视化其等值面。通过紫外-可见光分析法分析晶体的光学透明度，发现该晶体在可见光范围内具有良好的光学透明度，下截止波长为 326 nm。在光致发光光谱中，观察到 369 nm 处的宽发射峰。使用 FTIR 技术分析官能团，并比较实验值和理论值的振动频率。从 TG-DTA 研究推断，该晶体在高达 375 °C 时是热稳定的。Kurtz-Perry 粉末 SHG 分析也以 KDP 作为参考进行。结果表明，该晶体的效率是 KDP 的 1.08 倍。理论计算了分子的第一超极化张量，获得了理论二阶磁化率，并与实验磁化率进行了比较。结果表明，该晶体的效率是

  DOI：

  10.1016/j.molstruc.2018.12.071

文献信息

• Synthetic studies on duocarmycin. 2. Synthesis and cytotoxicity of natural (+)-duocarmycin A and its three possible stereoisomers.
  作者：Yasumichi Fukuda、Kazuhiko Nakatani、Shiro Terashima

  DOI：10.1016/s0040-4020(01)86994-5

  日期：1994.2

  types of the tricyclic intermediates and the synthetic scheme established in the synthesis of racemic compounds. In vitro cytotoxicity assay against P388 murine leukemia obviously showed that the absolute configuration of cyclopropane moiety in (+)-1 is closely related to its cytotoxicity.

  通过特征在于两种类型的三环中间体的光学拆分和在外消旋化合物的合成中建立的合成方案来实现标题合成。针对P388鼠白血病的体外细胞毒性试验显然表明（+）- 1中环丙烷部分的绝对构型与其细胞毒性密切相关。
• Novel asymmetric phenylselenium-induced lactamizations of olefinic amides: stereoselective routes to α- and β-amino acids
  作者：Sung-Kee Chung、Tae-Heum Jeong、Dong-Ho Kang

  DOI：10.1039/a705390h

  日期：——

  Organoselenium-induced cyclofunctionalization of the (S)-N-(α,β-unsaturated) acylprolinamides 1, 7 and 14 has been found to produce the 7-membered bislactam products 2 and 15, or the 6-membered phenylselenolactam products 8 and 9 depending on the substitution pattern of the enone moiety of the starting material. The structural identities and stereochemistry of the cyclized products have been determined by X-ray diffraction, and the diastereoselectivity in the formation of the 7-membered ring bislactam product was found to be 91.6% de. The mechanism of the cyclolactamization is discussed.

  有机硒诱导的(S)-N-(δ±,δ²-不饱和)酰基脯氨酰胺 1、7 和 14 的环功能化被发现可生成 7 元环双内酰胺产物 2 和 15，或 6 元环苯基硒内酰胺产物 8 和 9，这取决于起始原料的烯酮分子的取代模式。通过 X 射线衍射测定了环化产物的结构特征和立体化学性质，发现生成 7 元环双内酰胺产物的非对映选择性为 91.6%de。对环内酰胺化的机理进行了讨论。
• NOVEL 4H-3,1-BENZOXAZIN-4-ONE DERIVATIVE
  申请人：Japan Tobacco Inc.

  公开号：EP0480044A1

  公开（公告）日：1992-04-15

  A 4H-3,1-benzoxazin-4-one derivative of general formula (I), which has a potent serine protease inhibitory action and is useful as the active ingredient of drugs for preventing and treating pneumonia, pulmonary emphysema, pulmonary fibrosis, bronchitis, arthritis, pancreatitis, nephritis, shock, sepsis, arteriosclerosis, etc.; wherein R¹ represents lower alkyl; R² represents lower alkyl, lower alkylthioalkyl or lower alkanesulfinylalkyl; R³ represents hydrogen, hydroxyl, lower alkoxy or lower acyloxy; X represents a residue of an amino acid selected from the group consisting of alanine, valine and phenyl-alanine; n is an integer of 0, 1 or 2; and Y represents a substituent selected from the group consisting of C₂ to C₆ alkanoyl optionally substituted with phenyl, benzyloxycarbonyl, lower alkoxycarbonyl, cinnamoyl and methoxysuccinoyl.

  一种通式(I)的4H-3,1-苯并恶嗪-4-酮衍生物，它具有强效的丝氨酸蛋白酶抑制作用，可作为预防和治疗肺炎、肺气肿、肺纤维化、支气管炎、关节炎、胰腺炎、肾炎、休克、败血症、动脉硬化等药物的活性成分。其中 R¹ 代表低级烷基；R² 代表低级烷基、低级烷硫基烷基或低级烷磺基烷基；R³ 代表氢、羟基、低级烷氧基或低级酰氧基；X 代表选自丙氨酸、缬氨酸和苯丙氨酸的氨基酸残基；n 是 0、1 或 2 的整数；以及 Y 代表选自由苯基、苄氧羰基、低级烷氧羰基、肉桂酰基和甲氧基琥珀酰基取代的 C₂ 至 C₆ 烷酰基组成的取代基。
• Stereoselective Synthesis of β-Substituted Phenylalanine-β-phenylisoserine-Derived Tripeptides Using <i>N</i>-Cinnamoyl-<scp>l</scp>-proline as Template:  Synthesis of Structural Analogues of HIV Protease Inhibitors
  作者：Biswajit Saha、Jyoti Prokash Nandy、Shalini Shukla、Iffat Siddiqui、Javed Iqbal

  DOI：10.1021/jo0109826

  日期：2002.11.1

  N-Cinnamoyl-L-proline can be used as a template on which P-substituted phenylalanine and beta-phenylisoserine residues can be synthesized leading to tripeptide derivatives as structural analogues of HIV protease inhibitors.
• Characterization of the binding properties of SIRT2 inhibitors with a N-(3-phenylpropenoyl)-glycine tryptamide backbone
  作者：Päivi H. Kiviranta、Heikki S. Salo、Jukka Leppänen、Valtteri M. Rinne、Sergiy Kyrylenko、Erkki Kuusisto、Tiina Suuronen、Antero Salminen、Antti Poso、Maija Lahtela-Kakkonen、Erik A.A. Wallén

  DOI：10.1016/j.bmc.2008.07.059

  日期：2008.9

  SIRT2 inhibitors with a N-(3-phenylpropenoyl)-glycine tryptamide backbone were studied. This backbone has been developed in our group, and it is derived from a compound originally found by virtual screening. In addition, compounds with a smaller 3-phenylpropenoic acid tryptamide backbone were also included in the study. Binding modes for the new compounds and the previously reported compounds were analyzed with molecular modelling methods. The approach, which included a combination of molecular dynamics, molecular docking and cluster analysis, showed that certain docking poses were favourable despite the conformational variation in the target protein. The N-(3-phenylpropenoyl)-glycine tryptamide backbone is also a good backbone for SIRT2 inhibitors, and the series of compounds includes several potent SIRT2 inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.