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tert-Butyl-(3-ethyl-4-methyl-pyrrolyl-2)-methanoat | 75488-16-3

分子结构分类

有机化合物 - 有机杂环化合物 - 吡咯

中文名称

——

中文别名

——

英文名称

tert-Butyl-(3-ethyl-4-methyl-pyrrolyl-2)-methanoat

英文别名

t-butyl 3-ethyl-4-methyl-1H-pyrrole-2-carboxylate；tert-butyl 3-ethyl-4-methylpyrrole-2-carboxylate；t-butyl 3-ethyl-4-methyl-pyrrole-2-carboxylate；t-butyl 3-ethyl-4-methylpyrrole-2-carboxylate；tert-butyl 3-ethyl-4-methyl-1H-pyrrole-2-carboxylate

tert-Butyl-(3-ethyl-4-methyl-pyrrolyl-2)-methanoat化学式

CAS

75488-16-3

化学式

C₁₂H₁₉NO₂

mdl

——

分子量

209.288

InChiKey

BAIMXIFDWGMGJW-UHFFFAOYSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

322.7±30.0 °C(Predicted)
密度：

1.024±0.06 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

3
重原子数：

15
可旋转键数：

4
环数：

1.0
sp3杂化的碳原子比例：

0.58
拓扑面积：

42.1
氢给体数：

1
氢受体数：

2

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
2-(苄氧基羰基)-4-乙基-3-甲基吡咯-5-羧酸	5-Benzyloxycarbonyl-3-ethyl-4-methylpyrrole-2-carboxylic Acid	967-38-4	C₁₆H₁₇NO₄	287.315
——	benzyl 4-ethyl-3,5-dimethylpyrrole-2-carboxylate	1925-61-7	C₁₆H₁₉NO₂	257.332

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	tert-butyl 3-ethyl-4-formyl-1H-pyrrole-2-carboxylate	1224956-42-6	C₁₂H₁₇NO₃	223.272
——	2-O-tert-butyl 4-O-(3-hydroxypropyl) 3-ethyl-1H-pyrrole-2,4-dicarboxylate	1449604-10-7	C₁₅H₂₃NO₅	297.351
——	2-O-tert-butyl 4-O-(3-hydroxy-2,2-dimethylpropyl) 3-ethyl-1H-pyrrole-2,4-dicarboxylate	1449604-11-8	C₁₇H₂₇NO₅	325.405
——	tert-butyl 3-ethyl-5-[(5-formyl-4-methyl-1H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrole-2-carboxylate	620165-31-3	C₁₉H₂₆N₂O₃	330.427
——	tert-butyl 3-ethyl-5-[(5-formyl-3,4-dimethyl-1H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrole-2-carboxylate	620165-30-2	C₂₀H₂₈N₂O₃	344.454
——	5-[[4-ethyl-3-methyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-1H-pyrrol-2-yl]methyl]-3,4-dimethyl-1H-pyrrole-2-carboxylic acid	620165-28-8	C₂₀H₂₈N₂O₄	360.453
——	5'-t-butoxycarbonyl-3,4'-diethyl-5-formyl-3',4-dimethyldipyrrylmethane	83818-92-2	C₂₁H₃₀N₂O₃	358.481
——	5'-(tert-Butoxycarbonyl)-3,4'-diethyl-3',4-dimethylpyrromethane-5-carboxylic Acid	31862-33-6	C₂₁H₃₀N₂O₄	374.48
——	5'-(t-butoxycarbonyl)-3-(2-chloroethyl)-4'-ethyl-3',4-dimethyldipyrrylmethane-5-carboxylic acid	75488-05-0	C₂₁H₂₉ClN₂O₄	408.925
——	t-butyl-3,4'-dimethyl-4-ethyl-3'-(2-ethoxycarbonylethyl)-5'-formyldipyrrylmethane-5-carboxylate	128773-37-5	C₂₄H₃₄N₂O₅	430.544
——	benzyl 5'-(t-butyloxycarbonyl)-3-(2-chloroethyl)-4'-ethyl-3',4-dimethyldipyrrylmethane-5-carboxylate	75488-04-9	C₂₈H₃₅ClN₂O₄	499.05
——	t-butyl-3,4'-dimethyl-4-ethyl-3'-(2-ethoxycarbonylethyl)-5'-carboxydipyrrylmethane-5-carboxylate	128773-34-2	C₂₄H₃₄N₂O₆	446.544
——	benzyl-5-t-butoxycarbonyl-3,4'-dimethyl-4-ethyl-3'-(2-ethoxycarbonylethyl)-dipyrrylmethane-5'-carboxylate	128773-32-0	C₃₁H₄₀N₂O₆	536.668
——	tert-butyl 5-[[4-[4-[4-[bis[4-ethyl-3-methyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-1H-pyrrol-2-yl]methyl]phenyl]buta-1,3-diynyl]phenyl]-[4-ethyl-3-methyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-1H-pyrrol-2-yl]methyl]-3-ethyl-4-methyl-1H-pyrrole-2-carboxylate	127810-87-1	C₆₆H₈₂N₄O₈	1059.4
——	tert-butyl 5-[[4-[6-[4-[bis[4-ethyl-3-methyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-1H-pyrrol-2-yl]methyl]phenyl]hexa-1,3,5-triynyl]phenyl]-[4-ethyl-3-methyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-1H-pyrrol-2-yl]methyl]-3-ethyl-4-methyl-1H-pyrrole-2-carboxylate	127810-88-2	C₆₈H₈₂N₄O₈	1083.42
——	tert-butyl 5-[[4-[8-[4-[bis[4-ethyl-3-methyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-1H-pyrrol-2-yl]methyl]phenyl]octa-1,3,5,7-tetraynyl]phenyl]-[4-ethyl-3-methyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-1H-pyrrol-2-yl]methyl]-3-ethyl-4-methyl-1H-pyrrole-2-carboxylate	127810-89-3	C₇₀H₈₂N₄O₈	1107.44
——	tert-butyl 5-[[3-[4-[3-[bis[4-ethyl-3-methyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-1H-pyrrol-2-yl]methyl]phenyl]buta-1,3-diynyl]phenyl]-[4-ethyl-3-methyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-1H-pyrrol-2-yl]methyl]-3-ethyl-4-methyl-1H-pyrrole-2-carboxylate	127810-85-9	C₆₆H₈₂N₄O₈	1059.4
——	tert-butyl 5-[[3-[6-[3-[bis[4-ethyl-3-methyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-1H-pyrrol-2-yl]methyl]phenyl]hexa-1,3,5-triynyl]phenyl]-[4-ethyl-3-methyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-1H-pyrrol-2-yl]methyl]-3-ethyl-4-methyl-1H-pyrrole-2-carboxylate	127810-86-0	C₆₈H₈₂N₄O₈	1083.42
——	tert-butyl 5-[[3-[8-[3-[bis[4-ethyl-3-methyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-1H-pyrrol-2-yl]methyl]phenyl]octa-1,3,5,7-tetraynyl]phenyl]-[4-ethyl-3-methyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-1H-pyrrol-2-yl]methyl]-3-ethyl-4-methyl-1H-pyrrole-2-carboxylate	127824-59-3	C₇₀H₈₂N₄O₈	1107.44
——	tert-butyl 5-[[2-[4-[2-[bis[4-ethyl-3-methyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-1H-pyrrol-2-yl]methyl]phenyl]buta-1,3-diynyl]phenyl]-[4-ethyl-3-methyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-1H-pyrrol-2-yl]methyl]-3-ethyl-4-methyl-1H-pyrrole-2-carboxylate	127810-82-6	C₆₆H₈₂N₄O₈	1059.4
——	tert-butyl 5-[[2-[6-[2-[bis[4-ethyl-3-methyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-1H-pyrrol-2-yl]methyl]phenyl]hexa-1,3,5-triynyl]phenyl]-[4-ethyl-3-methyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-1H-pyrrol-2-yl]methyl]-3-ethyl-4-methyl-1H-pyrrole-2-carboxylate	127810-83-7	C₆₈H₈₂N₄O₈	1083.42

反应信息

作为反应物：

描述：

tert-Butyl-(3-ethyl-4-methyl-pyrrolyl-2)-methanoat 在 palladium on activated charcoal 氢溴酸、氢气、溴、苯甲酰氯、对甲苯磺酸、三乙胺作用下，以四氢呋喃、甲醇、二氯甲烷、三氟乙酸为溶剂， 40.0 ℃ 、344.73 kPa 条件下，反应 25.5h，生成 mesobiliverdin IXa dimethyl ester

参考文献：

名称：

The total synthesis of biliverdins of biological interest

摘要：

DOI：

10.1016/s0040-4020(01)87636-5
作为产物：

描述：

tert-butyl 3-ethyl-5-iodo-4-methylpyrrole-2-carboxylate 在 platinum(IV) oxide 氢气、 sodium acetate 作用下，以甲醇为溶剂，以94%的产率得到tert-Butyl-(3-ethyl-4-methyl-pyrrolyl-2)-methanoat

参考文献：

名称：

Clewlow, Paul J.; Jackson, Anthony H., Journal of the Chemical Society. Perkin transactions I, 1990, # 7, p. 1925 - 1936

摘要：

DOI：

点击查看最新优质反应信息

文献信息

Bile pigment studies-VII New syntheses of biliverdin-IXα dimethyl ester and two related mono-vinyl-mono-ethyl isomers

作者：Kevin M. Smith、Ravindra K. Pandey

DOI：10.1016/s0040-4020(01)91126-3

日期：1984.1

Using the recently developed route through di-t-butyl b-bilene-1,19-dicarboxylates, new syntheses of biliverdin-IXα dimethyl ester (1) and two related mono-vinyl-mono-ethyl isomers (2) and (3), are described. The two dihydro-derivatives of (1) are important in connection with biosynthetic studies of the origin of algal biliproteins.

使用最近开发的通过b-bilene-1,19-二羧酸二叔丁酯的路线，合成了biliverdin-IXα二甲基酯（1）和两个相关的单乙烯基-单乙基异构体（2）和（3）进行说明。（1）的两种二氢衍生物在藻类胆蛋白起源的生物合成研究中很重要。
Regioselective Oxidation of Pyrrole Derivatives with DDQ and Its Synthetic Application

作者：Ryoji Iwamoto、Yutaka Ukaji、Katsuhiko Inomata

DOI：10.1246/cl.2010.176

日期：2010.3.5

t-Butyl 4-alkyl-1H-pyrrole-2-carboxylates were oxidized with DDQ in the presence of MeOH at the α-position of the alkyl substituent at the C-4 position regioselectively to afford 4-acylpyrrole derivatives. On the other hand, treatment of the pyrroles with DDQ in the presence of AcOH furnished the corresponding 4-(1-acetoxyalkyl)pyrroles. The resulting 4-(acetoxymethyl)pyrrole reacted with various nucleophiles to afford the functionalized pyrrole derivatives in good yields.

t-丁基4-烷基-1H-吡咯-2-羧酸酯在甲醇存在下与DDQ氧化，选择性地在C-4位的烷基取代基的α位生成4-酰基吡咯衍生物。另一方面，将吡咯与DDQ和醋酸一起处理，得到相应的4-(1-乙酰氧基烷基)吡咯。所得的4-(乙酰氧基甲基)吡咯与各种亲核试剂反应，产生功能化的吡咯衍生物，产率良好。
Total synthesis of the porphyrin mineral abelsonite and related petroporphyrins with five-membered exocyclic rings

作者：Bo Zhang、Timothy D. Lash

DOI：10.1016/j.tetlet.2003.08.007

日期：2003.9

A reliable synthesis of porphyrins with five-membered exocyclic rings from b-bilenes has been developed. This methodology has been applied to the first total synthesis of the porphyrin mineral abelsonite, as well as the widespread petroporphyrin deoxophylloerythroetioporphyrin (DPEP) and its 3-desethyl analogue.

已开发了由b-比林可靠合成具有五元环外环的卟啉的方法。该方法已应用于卟啉矿物亚硒酸钠的首次全合成，以及广泛的石油卟啉脱氧叶绿体铁卟啉（DPEP）及其3-去乙基类似物。
Oxidation of Pyrrole-2-carboxylates with o-Chloranil and Its Synthetic Application

作者：Katsuhiko Inomata、Yutaka Ukaji、Ryoji Iwamoto、Shuhei Fujinami、Ryo Sakata

DOI：10.3987/com-10-s(e)110

日期：——

modified Barton reaction starting from aldehydes, 1-nitroalkanes, and isonitrile compounds. The produced tosyland ester-substituted pyrroles were converted into Aor D-ring and Bor C-ring, respectively. It would be ideal for the synthesis of the locked bilin chromophores if the various types of pyrroles and the related pyrrolinones could be available from a common pyrrole by a simple manipulation. Recently

3,4-二烷基-1H-吡咯-2-羧酸叔丁酯在甲醇存在下用邻氯苯胺氧化，得到相应的5-甲氧基吡咯啉-2-酮衍生物。得到的 5-methoxypyrrolin-2-one 在酸性条件下与各种亲核试剂反应，以良好的收率得到官能化的吡咯啉酮衍生物。为了阐明光敏色素中线性四吡咯 (bilin) 生色团的结构和功能，我们成功合成了植物色素 (PΦB)、藻蓝胆素 (PCB)、改性 PCB、胆绿素 (BV) 及其类似物，包括游离酸中的空间锁定衍生物通过开发制备每个吡咯环的有效方法以及它们之间的新偶联反应形成。为了合成不同类型的锁定发色团，有必要制备具有多种官能团的各种吡咯和吡咯啉酮衍生物。在我们之前的合成中，具有吸电子基团的吡咯环是通过从醛、1-硝基烷烃和异腈化合物开始的改进的巴顿反应构建的。生成的甲苯磺酸酯取代的吡咯分别转化为 Aor D 环和 Bor C 环。如果可以通过简单的操作从普通吡咯中获得各种
Concerning the mechanism of formation of biliverdins from b-bilenes

作者：Josefina Awruch

DOI：10.1016/s0040-4020(01)86682-5

日期：1990.1

The oxidation of 1,19-di-t-butoxycarbonyl-b-bilenes with bromine affords not only a major biliverdin, but also minor biliverdins. Elucidation of their structure revealed that cleavage of the b-bilene chain takes place during the oxidation, followed by dimerization of one dipyrrylmethene half. The synthesis of mesobiliverdins IX β , XI β, IV β , IX δ and coprobiliverdin II β are described.

1,19-二-叔丁氧基羰基-b-比林斯被溴氧化不仅提供了主要的胆绿素，还提供了次要的胆绿素。对它们的结构的阐明揭示了在氧化过程中发生了b-比林烯链的裂解，随后是一个二吡啶基亚甲基一半的二聚化。mesobiliverdins IX的合成β，XI β，IV β，IX δ和coprobiliverdin II β进行说明。