1-[(E)-cinnamoylamino]-pyrrolidine-2-carboxylic acid methyl ester | 159582-06-6

• 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: 1-[(E)-cinnamoylamino]-pyrrolidine-2-carboxylic acid methyl ester
• 英文别名: methyl 1-cinnamoylpyrrolidine-2-carboxylate；N-cinnamoyl L-proline methyl ester；methyl N-cinnamoyl-(L)-prolinate；N-cinnamoyl-L-proline methyl ester；methyl (2S)-1-[(E)-3-phenylprop-2-enoyl]pyrrolidine-2-carboxylate
• CAS: 159582-06-6
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: DPIZRDMBBNDGAO-LXKVQUBZSA-N

物化性质

• 沸点：
  436.1±44.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(E)-cinnamoylamino]-pyrrolidine-2-carboxylic acid methyl ester 在 polyaniline supported cobalt(II) acetate 氧气 、 异丁醛 作用下， 以 乙腈 为溶剂， 反应 35.0h， 以38%的产率得到(S)-1-(3-Phenyl-oxiranecarbonyl)-pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  聚苯胺负载的钴（II）催化剂：烯烃与分子氧的氧化

  摘要：

  聚苯胺负载的乙酸钴（II）在2-甲基丙醛的存在下，在环境温度下的氧气气氛下，催化不同烯烃的氧化。该催化剂可以进行环氧化反应而不会降低其催化效率。

  DOI：

  10.1016/s0040-4039(97)00045-2
• 作为产物：
  描述：

  L-脯氨酸甲酯盐酸盐 、 (E)-cinnamic (isobutyl carbonic) anhydride 在 三乙胺 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 1-[(E)-cinnamoylamino]-pyrrolidine-2-carboxylic acid methyl 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

文献信息

• 4H-3,1-benzoxazin-4-one derivative
  申请人：Japan Tobacco, Inc.

  公开号：US05204462A1

  公开（公告）日：1993-04-20

  4H-3,1-benzoxazin-4-one derivatives represented by formula (I) below: ##STR1## wherein R.sup.1 represents a lower alkyl group, R.sup.2 represents a lower alkyl group, a lower alkylthioalkyl group, or a lower alkanesulfinylalkyl group, R.sup.3 represents a hydrogen atom a hydroxyl group, a lower alkoxy group, or a lower acyloxy group, X represents an amino acid residue selected from the group consisting of alanine, valine, and phenylalanine, n represents an integer of 0, 1, or 2, and Y means a substituent selected from the group consisting of an alkanoyl group having 2 to 6 carbon atoms which may be substituted by a phenyl group, a benzyloxycarbonyl group, a lower alkoxycarbonyl group, a cinnamoyl group, and a methoxysuccinyl group. These derivatives exhibit a strong serine protease inhibiting effect, and are useful as effective components of agents for preventing and curing diseases caused by the excessive effect of serine proteases, e.g., pneumonia, pulmonary emphysema, fibroid lung, bronchitis, arthritis, pancreatitis, nephritis, shock, sepsis, and arteriosclerosis.

  以下是公式（I）所代表的4H-3,1-苯并噁嗪-4-酮衍生物的中文翻译：其中R.sup.1代表较低的烷基，R.sup.2代表较低的烷基，较低的烷硫烷基，或较低的烷基磺酰基，R.sup.3代表氢原子，羟基，较低的烷氧基，或较低的酰氧基，X代表从丙氨酸，缬氨酸和苯丙氨酸组成的氨基酸残基，n代表0、1或2的整数，Y表示从具有2至6个碳原子的烷酰基中选择的取代基，该基可能被苯基取代，苄氧羰基，较低的烷氧羰基，肉桂酰基和甲氧基琥珀酰基。这些衍生物表现出强烈的丝氨酸蛋白酶抑制作用，并可用作预防和治疗由丝氨酸蛋白酶过度作用引起的疾病的有效成分，例如肺炎，肺气肿，纤维肺，支气管炎，关节炎，胰腺炎，肾炎，休克，败血症和动脉硬化。
• Oxidative Amidation and Azidation of Aldehydes by NHC Catalysis
  作者：Suman De Sarkar、Armido Studer

  DOI：10.1021/ol1004643

  日期：2010.5.7

  N-Heterocyclic carbene catalyzed oxidative amidations of various aldehydes to the corresponding hexafluoroisopropylesters by using the readily available organic oxidant A are described. The hexafluoroisopropylesters prepared in situ are shown to be highly useful active esters for amide bond formation. In addition, oxidative azidation of aldehydes is presented. These mild organocatalytic processes do not use any

  描述了通过使用容易获得的有机氧化剂A的N-杂环卡宾催化的各种醛向相应的六氟异丙基酯的氧化酰胺化。已显示原位制备的六氟异丙基酯是用于酰胺键形成的高度有用的活性酯。另外，提出了醛的氧化叠氮化。这些温和的有机催化过程不使用任何过渡金属。
• Control of regioselectivity in nitrile oxide cycloadditions to cinnamic acid derivatives
  作者：Michele A. Weidner-Wells、Stephanie A. Fraga、James P. Demers

  DOI：10.1016/s0040-4039(00)78249-9

  日期：1994.8

  4-phenyl regioisomers 2b and 3b in a 25–30:75–70 ratio. This result is opposite to that obtained utilizing methyl cinnamate 1a as the dipolarophile. A synthetically useful method for the preparation of the acid 3c, derived from what is usually the minor regioisomer, has been developed by taking advantage of this reversal of regiochemistry.

  肉桂酸叔胺与苄腈氧化物进行环加成反应，生成比例为25-30：75-70的5-苯基和4-苯基区域异构体2b和3b。该结果与利用肉桂酸甲酯1a作为亲双性体获得的结果相反。通过利用区域化学的这种逆转，已经开发了用于制备酸3c的合成上有用的方法，所述酸3c通常由次要的区域异构体衍生而来。
• Enantiopure epoxidation of electrophilic alkenes
  作者：Otto Meth-Cohn、Yi Chen、David J. Williams

  DOI：10.1039/b000520g

  日期：——

  Cinnamamides derived from prolinols (e.g. –CH2OH and –CPh2OH) and from proline amides (e.g. prolineanilide) are epoxidised with total retention of the alkene configuration, to give either epoxides or bicyclic derivatives thereof, essentially enantiopure, using tert-butyl hydroperoxide and butyllithium.

  由脯氨醇（如-CH2OH和-CPh2OH）和脯氨酸酰胺（如脯氨酸苯胺）衍生的肉桂酰胺，在使用叔丁基过氧化氢和丁基锂进行环氧化时，可完全保留烯构型，得到环氧化物或其双环衍生物，基本上是不纯的。
• Stereoselective addition of CCl4 to 2S-methoxycarbonylN-(trans-cinnamoyl)pyrrolidine in the presence of Fe(CO)5 or Fe2(CO)9
  作者：R. G. Gasanov、S. O. Videnskaya、L. V. Il'inskaya

  DOI：10.1007/bf00700916

  日期：1995.7

  Addition of CCl4 to 2S-methoxycarbonyl-N-(trans-cinnamoyl)pyrrolidine in the presence of Fe(CO)5 or Fe2(CO)9 results in predominant formation of one of four possible optical isomers of the adduct PhCHClCH(CCl3)C(O)R (R=2S-methoxycarbonylpyrrolidyl).

  在 Fe(CO)5 或 Fe2(CO)9 存在下，CCl4 与 2S-甲氧基羰基-N-（反式肉桂酰基）吡咯烷的加成导致主要形成加合物 PhCHClCH(CCl3)C 的四种可能光学异构体之一(O)R (R=2S-甲氧羰基吡咯烷基)。