ethyl cis-(±)-2-hydroxycyclopentane-1-carboxylate | 1883-91-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: ethyl cis-(±)-2-hydroxycyclopentane-1-carboxylate
• 英文别名: ethyl cis-2-hydroxy-1-cyclopentane carboxylate；ethyl cis-2-hydroxy-1-cyclopentane-carboxylate；cis-ethyl 2-hydroxycyclopentane-1-carboxylate；ethyl cis-2-hydroxycyclopentanecarboxylate；ethyl 2-hydroxycyclopentanecarboxylate；cis-2-ethoxycarbonylcyclopentanol；cis-2-Hydroxy-cyclopentanecarboxylic acid ethyl ester；ethyl (1S,2R)-2-hydroxycyclopentane-1-carboxylate
• CAS: 1883-91-6；2315-21-1；54972-10-0；61586-79-6；63599-14-4；63599-15-5；110611-67-1；110611-68-2；122331-03-7
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: IIFIGGNBUOZGAB-NKWVEPMBSA-N

物化性质

• 沸点：
  230.8±33.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  常温常压下性质稳定，应避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38

反应信息

• 作为反应物：
  描述：

  ethyl cis-(±)-2-hydroxycyclopentane-1-carboxylate 在 palladium on activated charcoal lithium hydroxide 、 迭氮酸 、 氢气 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 23.0h， 生成 (1S,2s)-boc-2-氨基环戊烷羧酸
  参考文献：
  名称：

  Analogs of Ac-CCK-7 incorporating dipeptide mimics in place of Met28-Gly29

  摘要：

  A series of analogs of Ac-CCK-7 [Ac-Tyr(SO3H)-Met28-Gly29-Trp-Met-Asp-Phe-NH2, (1)] Were prepared in which the Met28-Gly29 dipeptide was replaced by omega-aminoalkanoic acids. Compounds were assessed in binding assays using homogenated rat pancreatic membranes and bovine striatum as the source of CCK-A and CCK-B receptors, respectively, and for anorectic activity after intraperitoneal administration to rats. The analog incorporating 4-aminobutanoic acid (5) was only 8 times less potent than 1 in the pancreatic binding assay, was more potent in the striatal binding assay, and was more potent than 1 in reducing food intake in rats. Using a bioactive cyclic analog of Ac-CCK-7 as a template, several rigid spacers were designed and tested as substitutes for the Met28-Gly29 dipeptide. The analogs incorporating 3-aminobenzoic acid (20) and (1S)-trans-2-aminocyclopentanecarboxylic acid (26) proved highly effective in the binding assays and as anorectic agents. We hypothesize that for stimulation of CCK-A receptors, the main function of the N-terminal tripeptide of Ac-CCK-7 is to orient the tyrosine sulfate with respect to Trp30 and that the bioactive arrangement of these elements lies among those which are readily available to both 20 and 26. NOESY and distance-constrained molecular dynamics experiments carried out on 20 and 26 identified conformations in which the relative orientation of the tyrosine hydroxide and the alpha-carbon atom of tryptophan were similar, providing the basis for further drug design efforts.

  DOI：

  10.1021/jm00099a005
• 作为产物：
  描述：

  ethyl 6-triethylsilyloxyhexanoate 在 RhCl(PPh₃)3 三甲基氯硅烷 、 4 Angstroem MS 、 diethylzinc 、 sodium acetate 、 对甲苯磺酸 、 pyridinium chlorochromate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 5.08h， 生成 ethyl cis-(±)-2-hydroxycyclopentane-1-carboxylate
  参考文献：
  名称：

  Rhodium-Catalyzed Reformatsky-Type Reaction

  摘要：

  [GRAPHICS]A novel Reformatsky type reaction was developed using RhCl(PPh3)(3) and diethylzinc. Inter- and intramolecular Reformatsky-type reactions were achieved efficiently under mild reaction conditions to give beta-hydroxy esters.

  DOI：

  10.1021/ol006268c

文献信息

• 14-Membered cyclodepsipeptides with alternating β-hydroxy and α-amino acids by cyclodimerization
  作者：Boyan Iliev、Anthony Linden、Roland Kunz、Heinz Heimgartner

  DOI：10.1016/j.tet.2005.11.002

  日期：2006.2

  cyclodimer 10. In all cases, when starting with racemic material, only the trans-substituted cyclodepsipeptides were isolated. Simple molecular modeling revealed that the formation of the cyclodimer is thermodynamically slightly more favorable than that of the cyclomonomer. The proposal that cyclodimer formation is preferred because of the presence of intramolecular H-bonds could not be confirmed by X-ray

  描述了在“直接酰胺环化”（DAC）条件下1型β-羟基酰胺的环二聚（孪生）。尽管其他偶联方法也可得出中等结果，但通过DAC可获得最佳收率，环二聚体10可达88％。在所有情况下，当从外消旋物质开始时，仅分离出反式取代的环二肽。简单的分子模型表明，环二聚体的形成在热力学上比环聚单体的形成稍微更有利。由于分子内氢键的存在，优选形成环二聚体的提议不能通过X射线晶体学证实。还研究了取代基在氨基酸和羟基酸部分中的影响。结果表明，仅当羟基酸部分被α，α-二取代时，环二聚作用才成功。
• A Stereoselective Synthesis of Phosphinic Acid Phosphapeptides Corresponding to Glutamyl-γ-glutamate and Incorporation into Potent Inhibitors of Folylpoly-γ-glutamyl Synthetase
  作者：David M. Bartley、James K. Coward

  DOI：10.1021/jo0507439

  日期：2005.8.1

  Radical addition of H3PO2 to N-/C-protected vinyl glycine led to the corresponding H-phosphinic acid in excellent yield. The non-nucleophilic H-phosphinic acid was converted to a nucleophilic PIII species, RP(OTMS)2, which was used in two approaches to the target phosphinic acid containing pseudopeptide. New methodology was developed that led to excellent yields in the reaction of RP(OTMS)2 with unactivated

  将H 3 PO 2自由基加到N- / C-保护的乙烯基甘氨酸中可得到相应的H-次膦酸，产率极高。将非亲核性H-次膦酸转化为亲核性的P III物种RP（OTMS）2，该物质以两种方法用于含有伪肽的目标次膦酸。开发了一种新的方法，可导致RP（OTMS）2与未活化的亲电试剂（包括无环均烯丙基溴）的反应获得优异的收率。然而，途中目标假肽，RP（OTMS）的阿尔布蜀夫反应2与环状高烯丙基溴，（ř）-3-（溴甲基）-环戊-1-烯导致重排的烯丙基次膦酸而不是所需的均烯丙基衍生物，即假定的谷氨酸替代物。将RP（OTMS）2共轭添加到含有手性助剂的α-亚甲基戊二酸酯中只会导致适度的非对映选择性。通过快速色谱纯化提供假肽的两种非对映异构体的保护衍生物。整体脱保护后，（S）-H-Glu-γ-[Ψ（P（O）（OH）（CH 2））]-（S）-Glu-OH与（S）-H-Glu-γ偶联-[Ψ（P（O）（OH）（CH 2
• Saturated heterocycless—35
  作者：Géza Stájer、Enikö A. Szabó、Ferenc Fülöp、Gábor Bernáth、Alajos Kálmán、Gyula Argay、Pál Sohár

  DOI：10.1016/s0040-4020(01)88695-6

  日期：1983.1

  5,6-Trimethylene-3,4,5,6-tetrahydro-1,3-oxazin-2-ones ane 2 thiones (11–20) were synthesized from cis and trans-2-aminomethylcyclopentanols (6–10) by reaction with urea ethyl chloroformate, carbon disulphide or thiophosgene. The cyclization reactions were also successful with the trans-amino-alcohols, at variance with earlier literature data relating to 1,2-disubstituted 1,3-bifunctional trans-cyclopentane

  顺式-和反式-5,6-三亚甲基-3,4,5,6-四氢-1,3-恶嗪-2-酮ANE 2个硫酮（11 - 20）从合成顺式和反式-2- aminomethylcyclopentanols（6 - 10）通过与尿素氯甲酸乙酯，二硫化碳或硫光气反应。反式-氨基醇的环化反应也成功，与早期文献数据有关，涉及1,2-二取代的1,3-双官能反式-环戊烷衍生物的X-射线衍射分析反式-5,6-三亚甲基- 3,4,5 6-四氢-1,3恶嗪-2-硫酮（17）表明，环外CXXXS sp 2键参与在S（10）O（1），N（3）和C（2）原子上形成的共平面离域pπ-pπ键系统，因此C（ 2）-N（3）[1.304（7）å]和C（2）-O（1）[1.337（7）å]键具有某些多重键特征。与相关杂环相比，C（2）和N（3）处的环内键角显着打开。在六元杂环的键中，C（5）-C（6）显着缩短[1.448（9）å]反式环戊烷衍生
• Synthesis and Pharmacological Evaluation of Identified and Putative Metabolites of the A₁ Adenosine Receptor Antagonist 8-Cyclopentyl-3-(3-fluoropropyl)-1-propylxanthine (CPFPX)
  作者：Marcus H. Holschbach、Dirk Bier、Wiebke Sihver、Annette Schulze、Bernd Neumaier

  DOI：10.1002/cmdc.201600592

  日期：2017.5.22

  The A1 adenosine receptor (A1 AR) antagonist [18 F]8-cyclopentyl-3-(3-fluoropropyl)-1-propylxanthine ([18 F]CPFPX), used in imaging human brain A1 ARs by positron emission tomography (PET), is stable in the brain, but rapidly undergoes transformation into one major (3-(3-fluoropropyl)-8-(3-oxocyclopenten-1-yl)-1-propylxanthine, M1) and several minor metabolites in blood. This report describes the synthesis

  A1腺苷受体（A1 AR）拮抗剂[18 F] 8-环戊基-3-（3-氟丙基）-1-丙基黄嘌呤（[18 F] CPFPX），用于通过正电子发射断层扫描（PET）对人脑A1 AR成像，在大脑中是稳定的，但迅速转变为血液中的一种主要的（3-（3-氟丙基）-8-（3-氧代环戊烯-1-基）-1-丙基黄嘌呤，M1）和几种次要的代谢物。该报告描述了CPFPX假定代谢产物的合成，作为鉴定这些代谢产物的标准。（放射）HPLC分析显示，未添加载体的（nca）[18 F] CPFPX孵育的人肝微粒体提取物含有主要代谢物M1，以及与在环戊基部分官能化的衍生物相对应的放射性代谢物，但没有因N3-氟丙基链功能化而产生的N1-去丙基物质或代谢产物。发现推定的代谢物在1.9和380 nm之间的Ki值处取代了[3 H] CPFPX与猪脑皮质中A1 AR的结合，并在Ki值处取代了猪纹状体中[3 H] ZM241385与A2A
• Immobilized baker's yeast reduction of ketones in an ionic liquid, [bmim]PF6 and water mix
  作者：Joshua Howarth、Paraic James、Jifeng Dai

  DOI：10.1016/s0040-4039(01)01601-x

  日期：2001.10

  The bioreduction with immobilized baker's yeast of several ketones was carried out in a 10:1 [bmim]PF6 ionic liquid/water mix. The reductions produced alcohols with comparable enantioselectivities to baker's yeast reductions in alternative media.

  在10：1 [bmim] PF 6离子液体/水混合物中，用固定化的贝克酵母对几种酮进行生物还原。还原产生的醇具有与面包酵母在替代培养基中的还原相当的对映选择性。