(E)-2-<(5R)-5-ethynyl-4,5,6,7-tetrahydro-5-<(triethylsilyl)oxy>spiro<2,1-benzisoxazole-7,2'-<1,3>dioxolan>-4-ylidene>acetic acid, methyl ester | 139609-34-0

分子结构分类

有机化合物 - 有机氧化合物

中文名称

——

中文别名

——

英文名称

(E)-2-<(5R)-5-ethynyl-4,5,6,7-tetrahydro-5-<(triethylsilyl)oxy>spiro<2,1-benzisoxazole-7,2'-<1,3>dioxolan>-4-ylidene>acetic acid, methyl ester

英文别名

(E)-2-[(5R)-5-Ethynyl-4,5,6,7-tetrahydro-5-[(triethylsilyl)oxy] spiro[2,1-benzisoxazole-7,2'-[1,3]dioxolan]-4-ylidene]acetic acid, methyl ester；methyl (2E)-2-[(5'R)-5'-ethynyl-5'-triethylsilyloxyspiro[1,3-dioxolane-2,7'-6H-2,1-benzoxazole]-4'-ylidene]acetate

(E)-2-<(5R)-5-ethynyl-4,5,6,7-tetrahydro-5-<(triethylsilyl)oxy>spiro<2,1-benzisoxazole-7,2'-<1,3>dioxolan>-4-ylidene>acetic acid, methyl ester化学式

CAS

139609-34-0

化学式

C₂₀H₂₇NO₆Si

mdl

——

分子量

405.523

InChiKey

XIUBEZFQNWQBGP-BAILOTOSSA-N

BEILSTEIN

——

EINECS

——

计算性质

辛醇/水分配系数(LogP)：

3.23
重原子数：

28
可旋转键数：

8
环数：

3.0
sp3杂化的碳原子比例：

0.6
拓扑面积：

80
氢给体数：

0
氢受体数：

7

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
——	(E)-2-<(5R)-5-ethynyl-4,5,6,7-tetrahydro-5-hydroxyspiro<2,1-benzisoxazole-7,2'-<1,3>dioxolan>-4-ylidene>acetic acid, methyl ester	139609-33-9	C₁₄H₁₃NO₆	291.26
——	(E)-2-<(5R)-5-acetoxy-4,5,6,7-tetrahydro-5-<2-(trimethylsilyl)ethynyl>spiro<2,1-benzisoxazole-7,2'-<1,3>dioxolan>-4-ylidene>acetic acid, methyl ester	139609-32-8	C₁₉H₂₃NO₇Si	405.48
——	(5R)-5-acetoxy-4,5,6,7-tetrahydro-5-<2-(trimethylsilyl)ethynyl>spiro<2,1-benzisoxazole-7,2'-<1,3>dioxolan>-4-one	139609-31-7	C₁₆H₁₉NO₆Si	349.415

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	(E)-2-<(5R)-4,5,6,7-tetrahydro-5-<(triethylsilyl)oxy>-5-<(3Z)-6-(trimethylsilyl)-3-hexene-1,5-diynyl>spiro<2,1-benzisoxazole-7,2'-<1,3>dioxolan>-4-ylidene>acetic acid, methyl ester	139609-35-1	C₂₇H₃₇NO₆Si₂	527.765
——	methyl (E)-2-((1R,8R,Z)-10-(1,3-dioxoisoindolin-2-yl)-8-((methylsulfonyl)oxy)-1-((triethylsilyl)oxy)spiro[bicyclo[7.3.1]tridecane-11,2'-[1,3]dioxolane]-4,9-dien-2,6-diyn-13-ylidene)acetate	139630-86-7	C₃₃H₃₅NO₁₀SSi	665.793
——	2-{(1'S,5'R,11'Z)-3'-oxo-5'-[(triethylsilyl)oxy]-5',6'-dihydro-1'H,3'H-spiro[1,3-dioxolane-2,7'-[1,5]hex[3]ene[1,5]diynoisochromen]-8'-yl}-1H-isoindole-1,3(2H)-dione	139609-41-9	C₃₁H₂₉NO₇Si	555.659
——	methyl (2E)-{(1R,4Z,8R)-10-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-8-hydroxy-1-[(triethylsilyl)oxy]-13H-spiro[bicyclo[7.3.1]trideca-4,9-diene-2,6-diyne-11,2'-[1,3]dioxolan]-13-ylidene}ethanoate	139609-40-8	C₃₂H₃₃NO₈Si	587.701
——	(E)-2-<(9R)-7-formyl-9-<(3Z)-3-hexene-1,5-diynyl>-6-phthalimido-9-<(triethylsilyl)oxy>-1,4-dioxaspiro<4,5>dec-6-en-8-ylidene>acetic acid, methyl ester	139609-39-5	C₃₂H₃₃NO₈Si	587.701
——	methyl (E)-2-((R,4aE,13Z)-2-((Z)-hexa-3-en-1,5-diyn-1-yl)-6,11-dioxo-2-((triethylsilyl)oxy)-2,3,6,11-tetrahydro-1H-spiro[dibenzo[c,g][1,5]oxazonine-4,2'-[1,3]dioxolan]-1-ylidene)acetate	139609-38-4	C₃₂H₃₃NO₈Si	587.701
——	methyl<(1'S,5'R)-5',6'-dihydro-3'-oxo-5'-<(triethylsilyl)oxy>spiro<1,3-dioxolane-2,7'(3'H)-<1,5><3>hexene<1,5>diyno<1H-2>benzopyran>-8'-yl>carbamate	225519-80-2	C₂₅H₂₉NO₇Si	483.593
——	N-{(R)-7-Formyl-9-((Z)-hex-3-ene-1,5-diynyl)-8-[1-methoxycarbonyl-meth-(E)-ylidene]-9-triethylsilanyloxy-1,4-dioxa-spiro[4.5]dec-6-en-6-yl}-phthalamic acid	150053-12-6	C₃₂H₃₅NO₉Si	605.717
——	methyl N-[(5'S,8'Z,12'R)-3'-oxo-12'-triethylsilyloxyspiro[1,3-dioxolane-2,14'-4-oxatricyclo[10.4.0.05,16]hexadeca-1,8,15-trien-6,10-diyne]-15'-yl]carbamate	139630-87-8	C₂₅H₂₉NO₇Si	483.593
——	methyl <1S-(1'R,3'RS,5'S,11'Z)>-<5'-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5',6'-dihydro-3'-hydroxyspiro<1,3-dioxolane-2',7'(3'H)-<1,5><3>hexene<1,5>diyno<1H-2>benzopyran>-8'-yl>carbamate	225368-22-9	C₂₅H₃₁NO₇Si	485.609
——	S-[(2E)-2-[(2'S,5'Z,9'R)-12'-(methoxycarbonylamino)-2',9'-bis(triethylsilyloxy)spiro[1,3-dioxolane-2,11'-bicyclo[7.3.1]trideca-1(12),5-dien-3,7-diyne]-13'-ylidene]ethyl] ethanethioate	139609-46-4	C₃₃H₄₉NO₇SSi₂	659.992
——	methyl N-[(1'R,4'Z,8'S,13'E)-13'-[2-(methyltrisulfanyl)ethylidene]-1',8'-bis(triethylsilyloxy)spiro[1,3-dioxolane-2,11'-bicyclo[7.3.1]trideca-4,9-dien-2,6-diyne]-10'-yl]carbamate	148111-43-7	C₃₂H₄₉NO₆S₃Si₂	696.113
——	[(2E)-2-[(2'S,5'Z,9'R)-12'-(methoxycarbonylamino)-2',9'-bis(triethylsilyloxy)spiro[1,3-dioxolane-2,11'-bicyclo[7.3.1]trideca-1(12),5-dien-3,7-diyne]-13'-ylidene]ethyl] 2,2-dimethylpropanoate	139609-44-2	C₃₆H₅₅NO₈Si₂	686.006
——	methyl ((1R,4Z,8S,13E)-13-(2-mercaptoethylidene)-1,8-bis((triethylsilyl)oxy)spiro[bicyclo[7.3.1]tridecane-11,2'-[1,3]dioxolane]-4,9-dien-2,6-diyn-10-yl)carbamate	148111-42-6	C₃₁H₄₇NO₆SSi₂	617.954
——	methyl ((1R,4Z,8S,13E)-8-hydroxy-13-(2-oxoethylidene)-1-((triethylsilyl)oxy)spiro[bicyclo[7.3.1]tridecane-11,2'-[1,3]dioxolane]-4,9-dien-2,6-diyn-10-yl)carbamate	1058156-33-4	C₂₅H₃₁NO₇Si	485.609
——	methyl N-[(1'R,4'Z,8'S,13'E)-13'-(2-hydroxyethylidene)-1',8'-bis(triethylsilyloxy)spiro[1,3-dioxolane-2,11'-bicyclo[7.3.1]trideca-4,9-dien-2,6-diyne]-10'-yl]carbamate	139609-45-3	C₃₁H₄₇NO₇Si₂	601.888
——	methyl {(1R,4Z,8S,13E)-8-hydroxy-13-(2-hydroxyethylidene)-1-[(triethylsilyl)oxy]spiro[bicyclo[7.3.1]trideca-4,9-diene-2,6-diyne-11,2'-[1,3]dioxolan]-10-yl}carbamate	139609-43-1	C₂₅H₃₃NO₇Si	487.625
——	free amine	139609-42-0	C₂₃H₂₇NO₅Si	425.557
——	(E)-2-<(9R)-6-amino-7-formyl-9-<(triethylsilyl)oxy>-9-<(3Z)-6-(trimethylsilyl)-3-hexene-1,5-diynyl>-1,4-dioxaspiro<4,5>dec-6-en-8-ylidene>acetic acid, methyl ester	139609-36-2	C₂₇H₃₉NO₆Si₂	529.781
——	(E)-2-<(9R)-6-amino-7-formyl-9-<(3Z)-3-hexene-1,5-diynyl>-9-<(triethylsilyl)oxy>-1,4-dioxaspiro<4,5>dec-6-en-8-ylidene>acetic acid, methyl ester	139609-37-3	C₂₄H₃₁NO₆Si	457.599

反应信息

作为反应物：

描述：

(E)-2-<(5R)-5-ethynyl-4,5,6,7-tetrahydro-5-<(triethylsilyl)oxy>spiro<2,1-benzisoxazole-7,2'-<1,3>dioxolan>-4-ylidene>acetic acid, methyl ester 在吡啶、甲醇、 4-二甲氨基吡啶、 copper(l) iodide 、四(三苯基膦)钯、 hexacarbonyl molybdenum 、水、 sodium methylate 、乙酸酐、 silica gel 、双(三甲基硅烷基)氨基钾、正丁胺、甲基肼作用下，以硝基甲烷、二氯甲烷、甲苯、乙腈、苯为溶剂，反应 27.75h，生成 methyl N-[(5'S,8'Z,12'R)-3'-oxo-12'-triethylsilyloxyspiro[1,3-dioxolane-2,14'-4-oxatricyclo[10.4.0.05,16]hexadeca-1,8,15-trien-6,10-diyne]-15'-yl]carbamate

参考文献：

名称：

Enantioselective total synthesis of (-)-calicheamicinone

摘要：

DOI：

10.1021/ja00034a068
作为产物：

描述：

在甲醇、草酰氯、 2,6-toluidine 、 sodium methylate 、二甲基亚砜作用下，以二氯甲烷、甲苯为溶剂，反应 28.5h，生成 (E)-2-<(5R)-5-ethynyl-4,5,6,7-tetrahydro-5-<(triethylsilyl)oxy>spiro<2,1-benzisoxazole-7,2'-<1,3>dioxolan>-4-ylidene>acetic acid, methyl ester

参考文献：

名称：

Enantioselective total synthesis of (-)-calicheamicinone

摘要：

DOI：

10.1021/ja00034a068

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文献信息

Analogs of calicheamicin gamma1I, method of making and using the same

申请人：The Scripps Research Institute

公开号：US05264586A1

公开（公告）日：1993-11-23

Chimeric analogs of calicheamicin that include an analog of calicheamicinone linked to an ester or glycoside, (-)-calicheamicinone and its analogs are disclosed.

揭示了卡利基阿霉素的嵌合类似物，其中包括与酯或糖苷相连的卡利基阿霉素酮的类似物，(-)-卡利基阿霉素酮及其类似物。
Smith; Pitsinos; Hwang, Journal of the American Chemical Society, 1993, vol. 115, # 17, p. 7612 - 7624

作者：Smith、Pitsinos、Hwang、Mizuno、Saimoto、Scarlato、Suzuki、Nicolaou

DOI：——

日期：——

(E)-2-<(5R)-5-ethynyl-4,5,6,7-tetrahydro-5-<(triethylsilyl)oxy>spiro<2,1-benzisoxazole-7,2'-<1,3>dioxolan>-4-ylidene>acetic acid, methyl ester | 139609-34-0

分子结构分类

计算性质

上下游信息

反应信息

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