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2-(epoxyethyl)-3,4-(isopropylidenedioxy)tetrahydrofuran | 226709-47-3

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

2-(epoxyethyl)-3,4-(isopropylidenedioxy)tetrahydrofuran

英文别名

1,2:3,6-dianhydro-4,5-O-isopropylidene-D-mannitol；O⁴,O⁵-isopropylidene-1,2;3,6-dianhydro-D-mannitol；O⁴,O⁵-Isopropyliden-1,2;3,6-dianhydro-D-mannit；(3aR,4R,6aR)-2,2-dimethyl-4-[(2R)-oxiran-2-yl]-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole

2-(epoxyethyl)-3,4-(isopropylidenedioxy)tetrahydrofuran化学式

CAS

226709-47-3

化学式

C₉H₁₄O₄

mdl

——

分子量

186.208

InChiKey

TZCGMHLATFFNHL-WCTZXXKLSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

27-28 °C
沸点：

75-85 °C(Press: 0.01 Torr)
密度：

1.221±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

辛醇/水分配系数(LogP)：

-0.1
重原子数：

13
可旋转键数：

1
环数：

3.0
sp3杂化的碳原子比例：

1.0
拓扑面积：

40.2
氢给体数：

0
氢受体数：

4

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
——	O²,O³-isopropyliden-1,4-anhydro-D-mannitol	71485-96-6	C₉H₁₆O₅	204.223
——	2-(1-hydroxy-2-iodoethyl)-3,4-(isopropylidenedioxy)tetrahydrofuran	188778-71-4	C₉H₁₅IO₄	314.12
——	1,4:3,6-dianhydro-D-mannitol	641-74-7	C₆H₁₀O₄	146.143

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	O²,O³-isopropyliden-1,4-anhydro-D-mannitol	71485-96-6	C₉H₁₆O₅	204.223
——	2-(1-hydroxyethyl)-3,4-(isopropylidenedioxy)tetrahydrofuran	226709-48-4	C₉H₁₆O₄	188.224
——	(3aR,4R,6aR)-4-[(1R)-1-decoxyethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole	226709-49-5	C₁₉H₃₆O₄	328.492
——	(3aR,4R,6aR)-4-[(1R)-1-dodecoxyethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole	226709-62-2	C₂₁H₄₀O₄	356.546
——	(3aR,4R,6aR)-2,2-dimethyl-4-[(1R)-1-tetradecoxyethyl]-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole	226709-63-3	C₂₃H₄₄O₄	384.6
——	(3aR,4R,6aR)-2,2-dimethyl-4-[(1R)-1-octadecoxyethyl]-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole	226709-64-4	C₂₇H₅₂O₄	440.707
——	(3aR,4R,6aR)-4-[(1R)-1-[12-[(1R)-1-[(3aR,4R,6aR)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]ethoxy]dodecoxy]ethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole	226709-53-1	C₃₀H₅₄O₈	542.754
——	2-(1-hydroxy-2-iodoethyl)-3,4-(isopropylidenedioxy)tetrahydrofuran	188778-71-4	C₉H₁₅IO₄	314.12
——	(R)-1-((3aR,4R,6aR)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-(isopropylamino)ethan-1-ol	1258071-29-2	C₁₂H₂₃NO₄	245.319
——	(R)-2-(tert-butylamino)-1-((3aR,4R,6aR)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)ethan-1-ol	1258071-30-5	C₁₃H₂₅NO₄	259.346
——	(R)-2-(cyclohexylamino)-1-((3aR,4R,6aR)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)ethan-1-ol	1258071-28-1	C₁₅H₂₇NO₄	285.384
——	(1R)-1-[(3aR,4R,6aR)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-(benzylamino)ethanol	1258071-24-7	C₁₆H₂₃NO₄	293.363
——	N-(tert-butyl)-1'H-spiro[cycloheptane-1,2'-quinoxalin]-3'-amine	1258071-27-0	C₁₇H₂₅NO₄	307.39
——	1,2:3,6-dianhydro-4,5-O-isopropylidene-1-thio-1-deoxy-D-glucitol	1333479-53-0	C₉H₁₄O₃S	202.274
——	(R)-1-((3aR,4R,6aR)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-(((R)-1-phenylethyl)amino)ethan-1-ol	1258071-25-8	C₁₇H₂₅NO₄	307.39
——	(R)-1-((3aR,4R,6aR)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-(((S)-1-phenylethyl)amino)ethan-1-ol	1258071-26-9	C₁₇H₂₅NO₄	307.39

反应信息

作为反应物：

描述：

2-(epoxyethyl)-3,4-(isopropylidenedioxy)tetrahydrofuran 在水作用下，生成 O²,O³-isopropyliden-1,4-anhydro-D-mannitol

参考文献：

名称：

247. 4：5-异亚丙基1：2-3：6-双脱水甘露醇

摘要：

DOI：

10.1039/jr9510001132
作为产物：

描述：

O²,O³-isopropyliden-1,4-anhydro-D-mannitol 在吡啶、甲醇、氯仿、 sodium methylate 作用下，生成 2-(epoxyethyl)-3,4-(isopropylidenedioxy)tetrahydrofuran

参考文献：

名称：

247. 4：5-异亚丙基1：2-3：6-双脱水甘露醇

摘要：

DOI：

10.1039/jr9510001132

点击查看最新优质反应信息

文献信息

Synthesis and assembly properties of a series of chiral amphiphilic dihydroxytetrahydrofuran derivatives

作者：S. Ejjiyar、C. Saluzzo、M. Massoui、R. Amouroux、N. Terry、A. W. Coleman

DOI：10.1002/1099-1395(200101)14:1<1::aid-poc325>3.0.co;2-c

日期：2001.1

The synthesis of a series of amphiphilic dihydroxytetrahydrofuran derivatives, prepared from isomannide and isosorbide, possessing hydrophobic ether chains lengths varying from C10 to C18 attached α to the tetrahydrofuran ring and with R and S chirality at the 0 linkage carbon atom is described. The interfacial properties of these compounds were studied using a Langmuir film balance; the results showed

描述了一系列由异甘露醇和异山梨醇制备的两亲性二羟基四氢呋喃衍生物的合成，这些衍生物具有从 C10 到 C18 不等的疏水醚链长度，α 连接到四氢呋喃环，并且在 0 键碳原子处具有 R 和 S 手性。使用朗缪尔薄膜天平研究了这些化合物的界面性质；结果表明，随着链长的增加，薄膜稳定性的预期增加以及与连接手性相关的相行为和薄膜稳定性的差异。动态光散射和非接触模式原子力显微镜研究了这些化合物的胶体分散体的形成。版权所有 © 2000 John Wiley & Sons, Ltd.
Synthesis and biological evaluation of sugar-derived chiral nitroimidazoles as potential antimycobacterial agents

作者：G. Mugunthan、Dharmarajan Sriram、Perumal Yogeeswari、K.P. Ravindranathan Kartha

DOI：10.1016/j.carres.2011.05.034

日期：2011.9

Chiral nitroimidazoles were synthesized using sugars as the chiral source. The synthesized compounds showed promising antimycobacterial property with MIC value in the range 6.25-12.5 mu g/mL against Mycobacterium tuberculosis H(37)Rv. (C) 2011 Elsevier Ltd. All rights reserved.
New class of β-aminoalcohol ligands derived from isosorbide and isomannide: application in hydrogen transfer reduction of prochiral ketones

作者：Tin Thanh Le、Stéphane Guillarme、Christine Saluzzo

DOI：10.1016/j.tet.2010.09.060

日期：2010.11

Starting from isosorbide and isomannide, two by-products from the starch industry, a family of chiral functionalized beta-aminoalcohols presenting a THF ring has been synthesized as potential ligands for hydrogen transfer reduction of prochiral ketones. Under optimal conditions, more than 70% ee with an excellent conversion were obtained for the HTR of the acetophenone. (C) 2010 Elsevier Ltd. All rights reserved.
O4,O5-ISOPROPYLIDENE-1,2:3,6-DIANHYDRO-D-GLUCITOL FROM ISOSORBIDE

作者：Ejjiyar、Saluzzo、Amouroux、Koga, Yuji、Uchiyama, Katsuya、Narasaka, Koichi

DOI：10.15227/orgsyn.077.0091

日期：——
763. Mechanism of the reaction of terminal vicinal ditoluene-p-sulphonyl hexitol derivatives with sodium iodide in acetone

作者：A. B. Foster、W. G. Overend

DOI：10.1039/jr9510003452

日期：——