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(-)-Kaitocephalin | 198710-92-8

分子结构分类

有机化合物 - 苯类化合物 - 苯和取代衍生物

中文名称

——

中文别名

——

英文名称

(-)-Kaitocephalin

英文别名

kaitocephalin；KCP；(2R,5R)-2-[(1S,2R)-2-amino-2-carboxy-1-hydroxyethyl]-5-[(2S)-2-carboxy-2-[(3,5-dichloro-4-hydroxybenzoyl)amino]ethyl]pyrrolidine-2-carboxylic acid

CAS

198710-92-8

化学式

C₁₈H₂₁Cl₂N₃O₉

mdl

——

分子量

494.285

InChiKey

AJQRDRIPQOAJCM-BWOKQULHSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

791.0±60.0 °C(Predicted)
密度：

1.648±0.06 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

-4.8
重原子数：

32
可旋转键数：

9
环数：

2.0
sp3杂化的碳原子比例：

0.44
拓扑面积：

220
氢给体数：

8
氢受体数：

11

SDS

SDS：7c787c6e5971578b71c6245e7f4e6f2f

查看

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
——	dibenzyl (2R,5R)-5-[(2S)-2-[(3,5-dichloro-4-phenylmethoxybenzoyl)amino]-3-oxo-3-phenylmethoxypropyl]-2-[(1S,2S)-1,3-dihydroxy-2-(phenylmethoxycarbonylamino)propyl]pyrrolidine-1,2-dicarboxylate	420107-69-3	C₅₅H₅₃Cl₂N₃O₁₂	1018.94
——	methyl (1S,5R,7aR)-5-((S)-2-(4-(benzyloxy)-3,5-dichlorobenzamido)-3-methoxy-3-oxopropyl)-1-((R)-1-((tert-butoxycarbonyl)amino)-2-methoxy-2-oxoethyl)-3-oxodihydro-1H,3H-pyrrolo[1,2-c]oxazole-7a(5H)-carboxylate	1276614-49-3	C₃₄H₃₉Cl₂N₃O₁₂	752.603
——	benzyl (2S,5R)-2-[(1S,2S)-2-azido-1,3-dihydroxypropyl]-2-(benzoyloxymethyl)-5-[(2S)-2-[(3,5-dichloro-4-phenylmethoxybenzoyl)amino]-3-hydroxypropyl]pyrrolidine-1-carboxylate	1438408-34-4	C₄₀H₄₁Cl₂N₅O₉	806.7
——	benzyl (2S,5R)-2-[(1S,2S)-2-azido-1-[tert-butyl(dimethyl)silyl]oxy-3-hydroxypropyl]-5-[(2S)-2-[(3,5-dichloro-4-phenylmethoxybenzoyl)amino]-3-hydroxypropyl]-2-(hydroxymethyl)pyrrolidine-1-carboxylate	1438408-37-7	C₃₉H₅₁Cl₂N₅O₈Si	816.854
——	1-O-tert-butyl 2-O-methyl (2R,5R)-5-[(E)-2-[(3,5-dichloro-4-phenylmethoxybenzoyl)amino]-3-methoxy-3-oxoprop-1-enyl]-2-[(1S,2R)-1-hydroxy-3-methoxy-3-oxo-2-(phenylmethoxycarbonylamino)propyl]pyrrolidine-1,2-dicarboxylate	1191124-99-8	C₄₁H₄₅Cl₂N₃O₁₃	858.727
——	1-O-tert-butyl 2-O-methyl (2R,5R)-5-formyl-2-[(1S,2R)-1-hydroxy-3-methoxy-3-oxo-2-(phenylmethoxycarbonylamino)propyl]pyrrolidine-1,2-dicarboxylate	1191124-92-1	C₂₄H₃₂N₂O₁₀	508.525
——	benzyl (2R,5R)-2-[(1S,2S)-3-[tert-butyl(diphenyl)silyl]oxy-2-(phenylmethoxycarbonylamino)-1-trimethylsilyloxypropyl]-5-[(2S)-2-[(3,5-dichloro-4-phenylmethoxybenzoyl)amino]-3-oxo-3-phenylmethoxypropyl]-1-hydroxypyrrolidine-2-carboxylate	420107-68-2	C₆₆H₇₃Cl₂N₃O₁₁Si₂	1211.4
——	(2R)-methyl 2-((1S,2R)-2-(methoxycarbonyl)-2-azido-1-hydroxyethyl)-5-oxopyrrolidine-2-carboxylate	866331-56-8	C₁₀H₁₄N₄O₆	286.244
——	methyl (1S,7aR)-1-[(1R)-2-methoxy-2-oxo-1-(phenylmethoxycarbonylamino)ethyl]-3,3-dimethyl-5-oxo-6,7-dihydro-1H-pyrrolo[1,2-c][1,3]oxazole-7a-carboxylate	866331-58-0	C₂₁H₂₆N₂O₈	434.446
——	methyl (1S,5R,7aR)-1-[(1R)-2-methoxy-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxoethyl]-5-[(2R)-3-methoxy-2-methylsulfonyloxy-3-oxopropyl]-3-oxo-1,5,6,7-tetrahydropyrrolo[1,2-c][1,3]oxazole-7a-carboxylate	1276614-47-1	C₂₁H₃₂N₂O₁₃S	552.557
——	benzyl (4S)-4-[(S)-[(3R,7aR)-3-tert-butyl-1-oxo-3,5,6,7-tetrahydropyrrolo[1,2-c][1,3]oxazol-7a-yl]-hydroxymethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate	420107-71-7	C₂₄H₃₄N₂O₆	446.544
——	(4R,5S)-3-benzyl 4-methyl 5-((R)-1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-5-oxopyrrolidin-2-yl)-2,2-dimethyloxazolidine-3,4-dicarboxylate	866331-60-4	C₂₆H₃₄N₂O₁₀	534.563
——	methyl (1S,5R,7aR)-5-(2,3-dihydroxypropyl)-1-[(4S)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidin-4-yl]-3-oxo-1,5,6,7-tetrahydropyrrolo[1,2-c][1,3]oxazole-7a-carboxylate	1276614-65-3	C₂₁H₃₄N₂O₉	458.509
——	methyl (1S,5R,7aR)-1-[(4S)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidin-4-yl]-3-oxo-5-prop-2-enyl-1,5,6,7-tetrahydropyrrolo[1,2-c][1,3]oxazole-7a-carboxylate	1276614-42-6	C₂₁H₃₂N₂O₇	424.494
——	(R)-2-[(1S,2S)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-trimethylsilanyloxy-propyl]-pyrrolidine-2-carboxylic acid benzyl ester	420107-63-7	C₄₂H₅₄N₂O₆Si₂	739.072
——	methyl (1S,5R,7aR)-5-[(2R)-3-[tert-butyl(dimethyl)silyl]oxy-2-methylsulfonyloxypropyl]-1-[(4S)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidin-4-yl]-3-oxo-1,5,6,7-tetrahydropyrrolo[1,2-c][1,3]oxazole-7a-carboxylate	1276614-45-9	C₂₈H₅₀N₂O₁₁SSi	650.863
——	(2R)-1-tert-butyl 2-methyl 2-((1R,2S)-2-(methoxycarbonyl)-1,2-dihydroxyethyl)-5-oxopyrrolidine-1,2-dicarboxylate	866331-53-5	C₁₅H₂₃NO₉	361.349
——	benzyl (1S,3S,7aR)-3-tert-butyl-1-[(1S)-2-[tert-butyl(diphenyl)silyl]oxy-1-(phenylmethoxycarbonylamino)ethyl]-3,5,6,7-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazole-7a-carboxylate	420107-62-6	C₄₄H₅₄N₂O₆Si	735.008

反应信息

作为反应物：

描述：

(-)-Kaitocephalin 在 sodium carbonate 、三甲基硅烷化重氮甲烷作用下，以 1,4-二氧六环、水为溶剂，生成 (1S,2S,5R,7aR)-2-tert-Butoxycarbonylamino-5-[(S)-2-(3,5-dichloro-4-methoxy-benzoylamino)-2-methoxycarbonyl-ethyl]-1-hydroxy-3-oxo-tetrahydro-pyrrolizine-7a-carboxylic acid methyl ester

参考文献：

名称：

Synthesis of the proposed structure and revision of stereochemistry of kaitocephalin

摘要：

A stereoselective total synthesis of the proposed structure of kaitocephalin (1) was accomplished starting from L-proline and D- and L-serines. How ever, its H-1 NMR spectral data and retention time oil HPLC were not identical with those of authentic natural kaitocephalin. The revised stereochemistry of natural kaitocephalin. (2R)-isomer (16), was inferred from further experiments employing diastereomers and model compounds. (C) 2002 Elsevier Science Ltd. All rights reserved.

DOI：

10.1016/s0040-4039(01)02254-7
作为产物：

描述：

benzyl (2S,5R)-2-((1S,2S)-2-azido-3-(benzoyloxy)-1-hydroxypropyl)-5-((S)-3-(benzoyloxy)-2-(4-(benzyloxy)-3,5-dichlorobenzamido)propyl)-2-((benzoyloxy)methyl)pyrrolidine-1-carboxylate 在 2,6-二甲基吡啶、 2-氮杂金刚烷-N-氧自由基、碘苯二乙酸、 20 wt.% Pd(OH)2 on activated carbon 、氢气、 potassium carbonate 作用下，以甲醇、 aq. phosphate buffer 、二氯甲烷、氯仿、乙腈为溶剂，反应 20.0h，生成 (-)-Kaitocephalin

参考文献：

名称：

Total synthesis of (−)-kaitocephalin

摘要：

(â)-Kaitocephalin 已被合成。利用来自加纳醛的 C9 立体中心，通过对 Cbz 保护的丝氨醇进行非对称化，安装了 C4 季碳。其余的立体中心是通过巯基环化、环氧化和区域选择性环氧化物开放生成的，其中季碳很可能在立体诱导过程中发挥了关键作用。

DOI：

10.1039/c3cc42365d

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文献信息

Reinvestigation on total synthesis of kaitocephalin and its isomers

作者：Shouyun Yu、Shaolin Zhu、Xianhua Pan、Jiade Yang、Dawei Ma

DOI：10.1016/j.tet.2010.12.068

日期：2011.3

Aldol reaction of 2,5-disubstituted pyrrolidine 3b with (R)-Garner aldehyde followed by Sharpless asymmetric dihydroxylation and other four reactions afforded mesylate 8a, which was introduced by an amide group via three ordinary transformations to provide amide 9a. Careful deprotection with AlCl3/Me2S and subsequent HPLC purification furnished kaitocephalin.

2,5-二取代的吡咯烷3b与（R）-加纳醛的Aldol反应，然后进行Sharpless不对称二羟基化反应和其他四个反应，得到甲磺酸盐8a，该甲磺酸盐由酰胺基经三个常规转化引入以提供酰胺9a。用AlCl 3 / Me 2 S小心地脱保护并随后进行HPLC纯化，得到的是海头脑素。
Total Synthesis of (−)-Kaitocephalin

作者：Masanori Kawasaki、Tetsuro Shinada、Makoto Hamada、Yasufumi Ohfune

DOI：10.1021/ol0515154

日期：2005.9.1

[reaction: see text] Total synthesis of the potent AMPA/KA receptor antagonist (-)-kaitocephalin (1) and its three diastereomers has been accomplished. The synthesis features strictly substrate-controlled operations to alpha-formylglutamate 3 starting with alpha-hydroxymethylglutamate 4. The requisite 2R,3S,7R-stereocenters were efficiently constructed by manipulation of stereoselective reactions:

[反应：见正文]已经完成了有效的AMPA / KA受体拮抗剂（-）-解脑磷脂（1）及其三种非对映异构体的全合成。该合成具有严格的底物控制操作，可从α-羟甲基谷氨酸4开始对α-甲酰基谷氨酸3进行操作。通过立体选择性反应的操作，可以有效地构建必需的2R，3S，7R-立体中心：7的二羟基化，然后叠氮化物取代相应的硫代碳酸盐10并与铜介导的酰酰亚胺离子21的烯丙基化反应同时通过AlCl3 / Me2S去除26个中的所有保护基，得到1。
A concise [C+NC+CC] coupling-enabled synthesis of kaitocephalin

作者：Philip Garner、Laksiri Weerasinghe、Ian Van Houten、Jieyu Hu

DOI：10.1039/c4cc01692k

日期：——

An efficient synthesis of the iGluR antagonist kaitocephalin is reported, employing an asymmetric [C+NC+CC] reaction in the key step.

报道了一种高效的iGluR拮抗剂kaitocephalin的合成方法，其中关键步骤采用不对称的[C+NC+CC]反应。
The first synthesis of kaitocephalin based on the structure revision

作者：Hidenori Watanabe、Masayuki Okue、Hiroyuki Kobayashi、Takeshi Kitahara

DOI：10.1016/s0040-4039(01)02255-9

日期：2002.1

A total synthesis of kaitocephalin (2), a glutamate receptor antagonist, was accomplished employing a novel stereoselective CC bond forming reaction of a nitrone (8) and a halide (11) with zinc in aqueous solvent under sonication as a key step. The absolute configuration of kaitocephalin was confirmed to be 2R,3S,4R,7R,9S.

关键步骤是在水溶液中超声处理硝酮（8）和卤化物（11）与锌的新型立体选择性CC键形成反应，完成了谷氨酸受体拮抗剂海德脑素（2）的全合成。kaitocephalin的绝对构型，确认为2 - [R，3小号，4 - [R，7 - [R 9小号。
PREPARATION OF HORNER-WADSWORTH-EMMONS REAGENT: METHYL 2-BENZYLOXYCARBONYLAMINO-2- (DIMETHOXY- PHOSPHINYL)ACETATE

作者：Azuma, Hiroki、Okano, Kentaro、Fukuyama, Tohru、Tokuyama, Hidetoshi

DOI：10.15227/orgsyn.088.0152

日期：——