(1S,4R)-4-N-acetylaminocyclopent-2-ene-1-ol | 205675-76-9

• 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: (1S,4R)-4-N-acetylaminocyclopent-2-ene-1-ol
• 英文别名: N-[(1R,4S)-4-hydroxycyclopent-2-en-1-yl]acetamide
• CAS: 205675-76-9
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: GOGHVYWKHJNKSK-NKWVEPMBSA-N

物化性质

• 沸点：
  361.3±42.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,4R)-4-N-acetylaminocyclopent-2-ene-1-ol 在 甲基磺酰氯 、 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of 1,2- and 1,4-amino alcohols from 1,3-dienes via oxazines. Rearrangements of 1,4-amino alcohol derivatives to oxazolines

  摘要：

  Conjugated dienes were converted to 1,2-oxazines by reaction with an acyl nitroso dienophile. The oxazines were reduced to 1,4-N-acetylamino alcohols, which were rearranged to the corresponding oxazolines upon treatment with methanesulfonyl chloride or anhydride. The oxazolines yielded 1,2-N-acetylamino alcohols upon hydrolysis. Thus either 1,4- or 1,2-N-acetylamino alcohols are available from 1,3-dienes via this methodology. Experimental and spectral data are provided for all new compounds. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.059
• 作为产物：
  描述：

  3-acetyl-2-oxa-3-azabicyclo[2.2.1]hept-5-ene 在 sodium tetrahydroborate 、 hexacarbonyl molybdenum 作用下， 生成 (1S,4R)-4-N-acetylaminocyclopent-2-ene-1-ol
  参考文献：
  名称：

  Enzymatic Resolution of Aminocyclopentenols as Precursors to d- and l-Carbocyclic Nucleosides

  摘要：

  Racemic cis-4-aminocyclopent-2-en-1-ols were synthesized in three steps utilizing hetero Diels-Alder chemistry. Starting from suitably protected hydroxylamines, oxidization with sodium periodate and trapping with cyclopentadiene afforded cycloadducts (+/-)-5a-d. The N-O bond of the cycloadducts was reduced with Mo(CO)(6) to afford (+/-)-cis-4-aminocyclopent-2-en-1-ols (+/-)-6a-d. These compounds, or their corresponding acetates, were kinetically resolved by enzymatic acetylation or hydrolysis, respectively. Enzymatic acetylation of cis-N-(benzylcarbamoyl)-4-aminocyclopent-2-enol [(+/-)-6a] with Candida antarctica B lipase and Pseudomonas species lipase gave the corresponding acetate (-)-7a in 90% and 92% ee, respectively, after 40% conversion. Enzymatic hydrolysis of cis-N-acetyl-4-aminocyclopent-2-enol 1-O-acetate (+/-)-7d with electric eel acetylcholine esterase was successful in providing both cis-N-acetyl-4-aminocyclopent-2-enols (+)ed and (+)-7d in 92% ee (99% ee after a single recrystallization) after 40% conversion. Further synthetic transformations of these resolved synthetic building blocks and derivatives are also reported.

  DOI：

  10.1021/jo972265a

文献信息

• Enantioselective Synthesis of 4-Acetylaminocyclopent-2-en-1-ols from Tricyclo[5.2.1.0^2,6]decenyl Enaminones. Precursors for 5‘-Norcarbocyclic Nucleosides and Related Antiviral Compounds
  作者：Namakkal G. Ramesh、Antonius J. H. Klunder、Binne Zwanenburg

  DOI：10.1021/jo982498h

  日期：1999.5.1

  6)]deca-4,8-dien-3-ones 14 and 15. N-Acetylation of both 15 and 14 followed by single electron-transfer reduction using lithium in liquid ammonia afforded diastereomeric mixtures of beta-amino ketones 26 and 27 and of ent-26 and ent-27 in high yields and with high diastereoselectivity. In this reduction process, the enaminone double bond is reduced with the concomitant removal of the alpha-methylbenzyl

  从对映体纯净的5-（1'-苯基乙基氨基）-内-三环[]开始有效地合成（1S，4R）和（1R，4S）-4-N-乙酰氨基-1-苯甲酰基环戊-2-烯33。 5.2.1.0（2,6）] deca-4,8-​​dien-3-one 14和15。15和14的N-乙酰化，然后在液氨中使用锂进行单电子转移还原，得到β-非对映异构体混合物氨基酮26和27以及ent-26和ent-27的收率高且非对映选择性高。在该还原过程中，烯胺酮双键被还原，同时伴随有作为手性助剂的α-甲基苄基的去除。在气相（FVT）中或在溶液中热解26和27的各自的非对映混合物，以高光学和化学收率得到4-N-乙酰氨基环戊-2-烯-1-酮30。（+）-30的酸性水解得到（R）-（+）-4-氨基环戊烯酮31为盐酸盐。使用硼氢化钠和七水合氯化铈进行立体选择性还原30，得到酰胺醇32，其经分离并表征为其苯甲酰基衍生物33。
• Enantioselective synthesis of (1 S ,4 R )- N -(benzylcarbamoyl)-4-aminocyclopent-2-en-1-ol by Candida antarctica lipase B
  作者：Hui-Jiao Wen、Qing Chen、Guo-Jun Zheng

  DOI：10.1016/j.cclet.2015.07.005

  日期：2015.11

  An efficient biocatalytic process has been developed to obtain optically pure (15,4R)-N-(benzylcarbamoy1)-4-aminocyclopent-2-en-1-ol which can be used as the key intermediate of ticagrelor. In this research, several N-(benzylcarbamoy1)-4-aminocyclopent-2-en-1-ol derivatives have been investigated in which Candida antarctica lipase B (CALB) was used to catalyze the asymmetric hydrolysis reaction. As expected, some of these substrates successfully gave (1S,4R)-N-(benzylcarbamoy1)-4-aminocyclopent2-en-1-ol in >98% enantiomeric excess (ee) with conversion yields up to 45%. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.