(S)-2-acetylpyrrolidine trifluoroacetate | 120966-83-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-2-acetylpyrrolidine trifluoroacetate
• 英文别名: (S)-pyrrolidin-2-yl-methylketone trifluoroacetic acid salt；1-[(2S)-pyrrolidin-2-yl]ethanone;2,2,2-trifluoroacetic acid
• CAS: 120966-83-8
• 化学式: C₂HF₃O₂*C₆H₁₁NO
• 分子量: 227.183
• InChiKey: HQZHGHSSNKMMPO-RGMNGODLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  73.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-acetylpyrrolidine trifluoroacetate 在 正丁基锂 、 mercury(II) perchlorate 作用下， 以 氯仿 为溶剂， 生成 (2S)-2-<(R)-1-(dimethoxymethyl)-1-hydroxyethyl>pyrrolidine
  参考文献：
  名称：

  Highly stereocontrolled total synthesis of (+)-allopumiliotoxin 339A

  摘要：

  DOI：

  10.1021/ja00052a081
• 作为产物：
  描述：

  (S)-N-Boc-吡咯烷-2-甲醛 N-(叔丁氧羰基)-L-脯氨醛 在 pyridine-SO3 complex 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 (S)-2-acetylpyrrolidine trifluoroacetate
  参考文献：
  名称：

  4-Phenylbutanoyl-2( S )-acylpyrrolidines and 4-phenylbutanoyl- l -prolyl-2( S )-acylpyrrolidines as prolyl oligopeptidase inhibitors

  摘要：

  New 4-phenylbutanoyl-2(S)-acylpyrrolidines and 4-phenylbutanoyl-L-prolyl-2(S)-acylpyrrolidines were synthesized. Their inhibitory activity against prolyl oligopeptidase from pig brain was tested in vitro. In the series of 4-phenylbutanoyl-2(S)-acylpyrrolidines, the cyclopentanecarbonyl and benzoyl derivatives were the best inhibitors having IC50 values of 30 and 23 nM, respectively. This series of compounds shows that that P1 pyrrolidine ring, which is common in most POP inhibitors, can be replaced by either a cyclopentyl ring or a phenyl ring, causing only a slight decrease in the inhibitory activity. In the series of 4-phenylbutanoyl-L-prolyl-2(S)- acyl-pyrrolidines, the cyclopentanecarbonyl and benzoyl derivatives were not as active as in the series of 4-phenylbutanoyl-2(S)-acylpyrrolidines, The hydroxyacetyl derivative did however show high inhibitors activity. This compound is structurally similar to JTP-4819, which is one of the most potent prolyl oligopeptidase inhibitors. The acyl group in the two series of new compounds seems to bind to different sites of the enzyme, since the second series of ne compounds did not show the same cyclopentanecarbonyl or benzoyl specificity as the first series. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00061-5

文献信息

• Isolation of Jahanene and Jahanane, and Total Synthesis of the Jahanyne Family
  作者：Arihiro Iwasaki、Haruka Fujimura、Shinichiro Okamoto、Takafumi Kudo、Shizuka Hoshina、Shimpei Sumimoto、Toshiaki Teruya、Kiyotake Suenaga

  DOI：10.1021/acs.joc.8b00310

  日期：2018.9.7

  and jahanane, highly N-methylated lipopeptides, were isolated from a marine cyanobacterium Okeania sp., and their structures were determined by NMR and MS. In addition, we achieved total syntheses of the jahanyne family and assessed their activities. The resulting growth-inhibitory activity of jahanyne was nearly one-tenth of the previously reported activity. Furthermore, we found that the degree of

  从海洋蓝藻Okeania sp。中分离出两个新的jahanyne类似物jahanene和jahanane，它们是高度N-甲基化的脂肽，其结构通过NMR和MS确定。此外，我们实现了贾哈妮家族的全部合成，并评估了他们的活动。所产生的jahanyne抑制生长的活性几乎是先前报道的活性的十分之一。此外，我们发现脂肪酸部分末端的不饱和度影响了对人类癌细胞的生长抑制活性。
• New and Convenient Syntheses of the Important Roasty, Popcorn-like Smelling Food Aroma Compounds 2-Acetyl-1-pyrroline and 2-Acetyltetrahydropyridine from Their Corresponding Cyclic α-Amino Acids
  作者：Thomas Hofmann、Peter Schieberle

  DOI：10.1021/jf9706437

  日期：1998.2.1

  Novel straightforward syntheses have been developed supplying the important food odorants 2-acetyl-1-pyrroline (AP) and 2-acetyltetrahydropyridine (ATHP) in high yields. The four-step reaction sequence starts from the N-shielded cyclic alpha-amino acids L-proline and pipecolinic acid, respectively, which, in the first step, are converted into the N-shielded 2-acetyl derivatives. Removing the shielding

  已经开发出新颖的简单合成方法，以高收率提供重要的食品增香剂2-乙酰基-1-吡咯啉（AP）和2-乙酰基四氢吡啶（ATHP）。四个步骤的反应序列分别从N-保护的环状α-氨基酸L-脯氨酸和胡椒碱酸开始，第一步将其转化为N-保护的2-乙酰基衍生物。用三氟乙酸除去保护基团，分别得到2-乙酰基吡咯烷和2-乙酰基哌啶三氟乙酸盐，将其水溶液的pH值提高到7.0后，它们以高收率自发地氧化成AP（基于L-脯氨酸的比例为43％）或ATHP（以胡椒碱酸计为35％），分别通过空气氧气。在食品中两种增香剂的形成途径仍不清楚的最后一步，这是重要的提示。
• Convergent Approach to Pumiliotoxin Alkaloids. Asymmetric Total Synthesis of (+)-Pumiliotoxins A, B, and 225F
  作者：Sakae Aoyagi、Shintaro Hirashima、Kosuke Saito、Chihiro Kibayashi

  DOI：10.1021/jo0200466

  日期：2002.8.1

  (Z)-iodoalkylidene indolizidine 34, which served as a common key intermediate, was synthesized through highly stereoselective addition of the chiral silylallene 19 to (S)-acetylpyrrolidine followed by a palladium-catalyzed intramolecular carbonylation[bond]cyclization sequence. This synthetic process allowed the first total synthesis of (+)-pumiliotoxin 225F. The intermediate (Z)-iodoalkylidene indolizidine 34 obtained

  利用Pd（0）催化的均烯酸有机锌和乙烯基碘化物之间的交叉偶联反应，已经开发了一种通用的会聚方法来制备pumiliotoxin生物碱。通过将手性甲硅烷基亚烷基19高度立体选择性地加成到（S）-乙酰基吡咯烷中，然后钯催化的分子内羰基化键合环化序列，合成了用作常见关键中间体的（Z）-碘亚烷基吲哚并吡啶34。该合成过程允许（+）-pumiliotoxin 225F的第一个全合成。将获得的中间体（Z）-碘亚烷基吲哚并吡啶34转化为均烯丙基氯化锌衍生物，并使用Pd（PPh（3））（4）催化剂与（E）-乙烯基碘42进行均烯丙基-乙烯基交叉偶联，得到带有1，5-二烯侧链的交叉偶联产物47。
• A convergent total synthesis of pumiliotoxins A and B via palladium-catalyzed cross-coupling reaction of homoallylic organozinc compounds with vinyl iodides
  作者：Chihiro Kibayashi、Sakae Aoyagi

  DOI：10.1016/s0022-328x(02)01160-9

  日期：2002.7

  pumiliotoxin alkaloids has been developed employing a Pd(0)-catalyzed cross-coupling reaction between homoallylic organozincs and vinyl iodides, which led to the asymmetric total synthesis of (+)-pumiliotoxins A (1) and B (2). The (Z)-alkylideneindolizidine, which is a common organic part of the organozinc reagents in this approach, was synthesized with a high degree of stereocontrol upon using HfCl4-mediated

  已经开发出一种通用的聚合方法来制备pumiliotoxin生物碱，该方法利用Pd（0）催化的均聚物有机锌与乙烯基碘之间的交叉偶联反应，导致（+）-pumiliotoxins A（1）和B的不对称全合成。（2）。在这种方法中，作为有机锌试剂的常见有机部分的（Z）-亚烷基亚吲哚并咪唑是通过使用HfCl 4介导的将烯丙基硅烷加到（S）-2-乙酰基吡咯烷中而以高度立体控制合成的。（Z）-碘亚烷基亚吲哚并核苷（31如此获得的作为高级通用中间体）被转化为高烯丙基氯化锌衍生物32，使用Pd（PPh 3）4催化剂与（E）-乙烯基碘化物（13）进行高烯丙基-乙烯基交叉偶联，得到1,5 -二烯产物33。随后的脱保护作用提供了（+）-pumiliotoxinA。另一方面，将31转化为均烯丙基叔丁基锌中间体39，该中间体与（E）-乙烯基碘化物（36）交联。 Pd（0）催化剂。所得的1，5-二烯产物40 进行后续的
• [EN] COMPOUNDS HAVING PROLYL OLIGOPEPTIDASE INHIBITORY ACTIVITY, METHODS FOR THEIR PREPARATION AND THEIR USE<br/>[FR] COMPOSES INHIBITEURS DE LA PROLYL OLIGOPEPTIDASE, PROCEDES DE PREPARATION ET UTILISATION
  申请人：ORION CORP

  公开号：WO2003004468A1

  公开（公告）日：2003-01-16

  Compounds of the formula (I), wherein the symbol aa means a residue of an α-amino acid. The invention is also directed to a method for the preparation of the compounds of formula (I), as well as their use as prolyl oligopeptide inhibitors, for example for the treatment of Alzheimer's disease.

  公式（I）的化合物，其中符号aa表示α-氨基酸的残基。本发明还涉及一种制备公式（I）化合物的方法，以及它们作为脯氨酰寡肽抑制剂的用途，例如用于治疗阿尔茨海默病。