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diphenylmethyl 6,6-dibromopenicillanate | 75527-84-3

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

diphenylmethyl 6,6-dibromopenicillanate

英文别名

O-diphenylmethyl 6,6-dibromopenicillanic acid；6,6-dibromopenicillin diphenylmethyl ester；benzhydryl 6,6-dibromopenicillanate；benzhydryl 6,6-dibrompenicillinate；6,6-dibromopenicillanate；(2S,5R,6S)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester；benzhydryl (2S,5R)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

diphenylmethyl 6,6-dibromopenicillanate化学式

CAS

75527-84-3

化学式

C₂₁H₁₉Br₂NO₃S

mdl

——

分子量

525.261

InChiKey

SSLOATPLZXISQE-QFBILLFUSA-N

BEILSTEIN

——

EINECS

——

物化性质

溶解度：

溶于二氯甲烷

计算性质

辛醇/水分配系数(LogP)：

5.4
重原子数：

28
可旋转键数：

5
环数：

4.0
sp3杂化的碳原子比例：

0.33
拓扑面积：

71.9
氢给体数：

0
氢受体数：

4

SDS

SDS：70faf49b280849a767ca6d308412d040

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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
6,6-二溴青霉烷酸	6,6-Dibromopenicillanic acid	24158-88-1	C₈H₉Br₂NO₃S	359.038
——	(2S,5R)-6,6-dibromo-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	——	C₈H₉Br₂NO₄S	375.038
——	6-aminopenicillanic acid	——	C₈H₁₂N₂O₃S	216.261
6-氨基青霉烷酸	6-Aminopenicillanic Acid	551-16-6	C₈H₁₂N₂O₃S	216.261

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	benzhydryl 6β-bromopenicillanate	75527-85-4	C₂₁H₂₀BrNO₃S	446.365
舒巴坦杂质18	benzhydryl 6α-bromopenicillanate	74189-25-6	C₂₁H₂₀BrNO₃S	446.365
——	diphenylmethyl 6β-bromo-6α-(hydroxymethyl)penicillanate	81324-31-4	C₂₂H₂₂BrNO₄S	476.391
——	benzhydryl 6,6-dihydropenicillate	73968-83-9	C₂₁H₂₁NO₃S	367.469
——	(2S,5R)-6,6-dibromo-3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester	81324-43-8	C₂₁H₁₉Br₂NO₅S	557.26
——	6α-bromo-6β-(1-hydroxyethyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester	91618-40-5	C₂₃H₂₄BrNO₄S	490.418
——	diphenylmethyl (1'S,3S,5R,6R)-6-bromo-6-(1'-hydroxyethyl)penicillanate	1058218-57-7	C₂₃H₂₄BrNO₄S	490.418
——	diphenylmethyl 6α-bromo-6β-(1-hydroxy-1-methylethyl)penicillanate	1160463-30-8	C₂₄H₂₆BrNO₄S	504.445
——	diphenylmethyl 6β-(hydroxymethyl)penicillanate	76517-80-1	C₂₂H₂₃NO₄S	397.495
——	diphenylmethyl 6α-(hydroxymethyl)penicillanate	81324-18-7	C₂₂H₂₃NO₄S	397.495
——	benzhydryl 6α-(2'-acetoxyethyl)penicillanate	108834-84-0	C₂₅H₂₇NO₅S	453.559
——	benzhydryl 6α-allylpenicillanate	108834-94-2	C₂₄H₂₅NO₃S	407.533
——	benzhydryl 6α-(2'-cyanoethyl)penicillanate	108834-82-8	C₂₄H₂₄N₂O₃S	420.532
——	benzhydryl 6α-(2'-carbomethoxyethyl)pencillanate	108834-83-9	C₂₅H₂₇NO₅S	453.559
——	benzhydryl 6,6-diallylpenicillanate	108834-95-3	C₂₇H₂₉NO₃S	447.598
——	benzhydryl (2S,5R,6R)-6-(hydroxymethyl)-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	81324-22-3	C₂₂H₂₃NO₆S	429.494
——	2'-carboethoxyspiro(benzhydryl penicillanate-6-1'-cyclopropane)	88065-50-3	C₂₆H₂₇NO₅S	465.57
——	(2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-oxo-ethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester	305796-42-3	C₂₃H₂₃NO₆S	441.505
——	(2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-(2-propenyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester	176220-76-1	C₂₄H₂₅NO₅S	439.532
——	2-O-benzhydryl 1-O',1-O'-diethyl (2S,5R,6R)-3,3-dimethyl-7-oxospiro[4-thia-1-azabicyclo[3.2.0]heptane-6,2'-cyclopropane]-1',1',2-tricarboxylate	88065-52-5	C₂₉H₃₁NO₇S	537.634
——	2-O-benzhydryl 1-O',1-O'-diethyl (2S,5R,6S)-3,3-dimethyl-7-oxospiro[4-thia-1-azabicyclo[3.2.0]heptane-6,2'-cyclopropane]-1',1',2-tricarboxylate	88065-52-5	C₂₉H₃₁NO₇S	537.634
——	2-O-benzhydryl 1-O'-ethyl (1'R,2S,5R,6R)-3,3-dimethyl-4,4,7-trioxospiro[4lambda6-thia-1-azabicyclo[3.2.0]heptane-6,2'-cyclopropane]-1',2-dicarboxylate	88228-72-2	C₂₆H₂₇NO₇S	497.569
——	6β-hydroxymethylpenicillanic acid	76517-64-1	C₉H₁₃NO₄S	231.273
——	(2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-[[(2-phenylacetyl)amino]methyl]-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	1266323-90-3	C₁₇H₂₀N₂O₆S	380.422
——	6-beta-(Aminomethyl)-penicillanic Acid 1,1-Dioxide	87353-34-2	C₉H₁₄N₂O₅S	262.287
——	(2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-[(trifluoromethylsulfonylamino)methyl]-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	1266323-87-8	C₁₀H₁₃F₃N₂O₇S₂	394.35
——	(2S,5R,6R)-3,3-dimethyl-4,4,7-trioxo-6-[(prop-2-enoxycarbonylamino)methyl]-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	1266323-84-5	C₁₃H₁₈N₂O₇S	346.361
——	(2S,5R,6R)-6-(formamidomethyl)-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	1266323-85-6	C₁₀H₁₄N₂O₆S	290.297
——	(2S,5R,6R)-6-[(2,2-dimethylpropanoylamino)methyl]-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	1266323-86-7	C₁₄H₂₂N₂O₆S	346.404
——	(2S,5R,6R)-6-(2,2-dihydroxyethyl)-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	1266323-82-3	C₁₀H₁₅NO₇S	293.298
——	(2S,5R,6R)-6-(2-hydroxyethyl)-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	1266323-83-4	C₁₀H₁₅NO₆S	277.298
——	6β-hydroxymethylsulbactam	81324-33-6	C₉H₁₃NO₆S	263.271
——	(2S,5R,6R)-6-[2-(hydroxyamino)-2-oxoethyl]-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	1266323-88-9	C₁₀H₁₄N₂O₇S	306.296
——	(2S,5R,6R)-6-(3-hydroxypropyl)-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	1266323-81-2	C₁₁H₁₇NO₆S	291.325
——	(2S,2'R,3'R,5R)-2',3'-bis(ethoxycarbonyl)-3,3-dimethyl-7-oxospiro[4-thia-1-azabicyclo[3.2.0]heptane-6,1'-cyclopropane]-2-carboxylic acid	88065-58-1	C₁₆H₂₁NO₇S	371.411
——	(2S,5R,6R)-6-(carboxymethyl)-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	1266323-89-0	C₁₀H₁₃NO₇S	291.282
——	6β-allyl-penicillanic acid 1,1-dioxide	123361-44-4	C₁₁H₁₅NO₅S	273.31
——	(2S,5R,6S)-6-Mercaptomethyl-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid	——	C₉H₁₃NO₅S₂	279.338
——	(2S,2'R,5R,6R)-2'-ethoxycarbonyl-3,3-dimethyl-7-oxospiro[4-thia-1-azabicyclo[3.2.0]heptane-6,1'-cyclopropane]-2-carboxylic acid	88065-56-9	C₁₃H₁₇NO₅S	299.348
——	(6E)-benzylidenepenicillanic acid 1,1-dioxide	98153-45-8	C₁₅H₁₅NO₅S	321.354
——	(2S,5R,6R)-1',1'-bis(ethoxycarbonyl)-3,3-dimethyl-7-oxospiro[4-thia-1-azabicyclo[3.2.0]heptane-6,2'-cyclopropane]-2-carboxylic acid	88065-59-2	C₁₆H₂₁NO₇S	371.411
——	(2S,5R,6R)-6-(1-hydroxy-2-oxo-2-pyrrolidin-1-ylethyl)-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	1266323-80-1	C₁₄H₂₀N₂O₇S	360.388

反应信息

作为反应物：

描述：

diphenylmethyl 6,6-dibromopenicillanate 在甲基溴化镁、间氯过氧苯甲酸作用下，以四氢呋喃、二氯甲烷为溶剂，反应 3.5h，生成 benzhydryl (2S,5R)-6-bromo-6-(hydroxymethyl)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

参考文献：

名称：

青霉素砜 C6 取代基的修饰，旨在提高抑制剂识别和功效

摘要：

通过合成和评估一系列系统的 6β-取代青霉素砜，评估了氢键供给取代基对 β-内酰胺酶抑制活性的重要性。

DOI：

10.1016/j.bmcl.2010.10.134
作为产物：

描述：

6-aminopenicillanic acid 在 sodium nitrite 作用下，以二氯甲烷、水为溶剂，反应 4.33h，生成 diphenylmethyl 6,6-dibromopenicillanate

参考文献：

名称：

一种他唑巴坦中间体6-溴青霉烷酸二苯甲酯亚砜的制备方法

摘要：

本发明提供一种他唑巴坦中间体6‑溴青霉烷酸二苯甲酯亚砜的制备方法，包括以下步骤：该方法以6‑APA为原料，经过氢溴酸溶液，亚硝酸钠，双氧水溴化反应生成6‑APA二溴产物；再与二苯基重氮甲烷酯化；然后与焦亚硫酸钠反应变成青霉烷酸二苯甲酯单溴物，经过双氧水氧化生成他唑巴坦中间体6‑溴青霉烷酸二苯甲酯亚砜。整个合成路线的原料均廉价易得，操作简便，收率高，操作成本低，工艺绿色环保，十分适合于工业化生产，具有极强的工业应用价值。

公开号：

CN108822132A

点击查看最新优质反应信息

文献信息

Regiospecific Syntheses of 6α-(1<i>R</i>-Hydroxyoctyl)penicillanic Acid and 6β-(1<i>R</i>-Hydroxyoctyl)penicillanic Acid as Mechanistic Probes of Class D β-Lactamases

作者：Sebastian A. Testero、Peter I. O’Daniel、Qicun Shi、Mijoon Lee、Dusan Hesek、Akihiro Ishiwata、Bruce C. Noll、Shahriar Mobashery

DOI：10.1021/ol900668k

日期：2009.6.18

The unique hydrophobic surface patches in class D β-lactamases presented an opportunity for designing two compounds, 6α-(1R-hydroxyoctyl)penicillanic acid and 6β-(1R-hydroxyoctyl)penicillanic acid, as mechanistic probes of these enzymes. In a sequence of three synthetic steps from benzhydryl 6,6-dibromopenicillanate, the targeted compounds were prepared in a stereospecific manner.

在d类β内酰胺酶的独特的疏水性表面贴片提供了一个机会来设计两种化合物，6α-（1 - [R -羟基辛基）青霉烷酸和6β-（1 - [R -羟基辛基）青霉烷酸，因为这些酶的机械探针。在 6,6-二溴青霉酸二苯甲基酯的三个合成步骤序列中，目标化合物以立体特异性方式制备。
Stereoselective Reduction of α-Bromopenicillanates by Tributylphosphine

作者：Akihiro Ishiwata、Lakshmi P. Kotra、Kazuyuki Miyashita、Tsuyoshi Nagase、Shahriar Mobashery

DOI：10.1021/ol000185e

日期：2000.9.1

[reaction: see text] Diastereoselective reduction of 6-bromo-6-substituted penicillanate esters has been achieved by treatment with tributylphosphine to give 6-substituted penicillanate esters. This reaction would appear to proceed through a phosphonium beta-lactam enolate species, followed by a diastereoselective protonation. This method has the advantage of being simple to carry out and it is mild

[反应：见正文]通过用三丁基膦处理得到6-取代的青霉酸酯，已经实现了6-溴-6-取代的青霉酸酯的非对映选择性还原。该反应似乎通过through-β-内酰胺烯醇化species物种进行，随后是非对映选择性质子化。该方法的优点是易于实施，并且温和，非对映选择性高，并且应能耐受底物中的许多官能团。这些意见的含义进行了讨论。
C类β-内酰胺酶抑制剂及其制备方法和应用

申请人：香港理工大学深圳研究院

公开号：CN109422765B

公开（公告）日：2020-08-28

本发明提供了一种C类β‑内酰胺酶抑制剂，所述C类β‑内酰胺酶抑制剂为6α‑(1R‑羟基‑3(2‑噻吩‑基)丙基)青霉素酸，具有如下式1所示结构，
Penicillin-derived inhibitors that simultaneously target both metallo- and serine-β-lactamases

作者：John D. Buynak、Hansong Chen、Lakshminaryana Vogeti、Venkat Rao Gadhachanda、Christine A. Buchanan、Timothy Palzkill、Robert W. Shaw、James Spencer、Timothy R. Walsh

DOI：10.1016/j.bmcl.2003.12.037

日期：2004.3

The synthesis and beta-lactamase inhibitory activity of four 6-(mercaptomethyl)penicillinates and the four corresponding 6-(hydroxymethyl)penicillinates are described. These penicillins include both C6 stereoisomers as well as the sulfide and sulfone oxidation states of the penam thiazolidine sulfur. All compounds were evaluated as inhibitors of representative metallo- and serine-beta-lactamases enzymes

描述了四种6-（巯基甲基）青霉酸酯和四种相应的6-（羟甲基）青霉酸酯的合成和β-内酰胺酶抑制活性。这些青霉素包括C6立体异构体以及戊二噻唑烷硫的硫化物和砜的氧化态。评价所有化合物作为代表性金属-和丝氨酸-β-内酰胺酶的抑制剂。显示选择的（巯基甲基）青霉酸酯可灭活金属-和丝氨酸-β-内酰胺酶，并显示出与哌拉西林对产生β-内酰胺酶的菌株的协同作用。
.beta.-Bromopenicillanic acid sulfone

申请人：E. R. Squibb & Sons, Inc.

公开号：US04203992A1

公开（公告）日：1980-05-20

(2S,5R,6S)-6.beta.-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hepta ne-2-carboxylic acid, S,S-dioxide, physiologically acceptable salts thereof and readily hydrolyzable ester thereof inhibit the action of the .beta.-lactamase enzyme RTEM.

(2S,5R,6S)-6-β-溴-3,3-二甲基-7-氧代-4-硫代-1-氮杂双环[3.2.0]庚烷-2-羧酸，S,S-二氧化物，其生理可接受的盐和容易水解的酯类，能够抑制β-内酰胺酶酶RTEM的作用。