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392723

(DHQ)₂PHAL

Name: (DHQ)<SUB>2</SUB>PHAL
Brand: ALDRICH

≥95%

别名:

氢化奎宁 1,4-(2,3-二氮杂萘)二醚

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About This Item

经验公式（希尔记法）:

C₄₈H₅₄N₆O₄

CAS号:

140924-50-1

分子量:

778.98

Beilstein:

5475677

MDL號碼:

MFCD00191975

分類程式碼代碼:

12352005

PubChem物質ID:

24864480

NACRES:

NA.22

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Sigma-Aldrich

392731

(DHQD)₂PHAL

Sigma-Aldrich

392758

AD-mix-α

Sigma-Aldrich

209104

锇酸钾二水合物

Sigma-Aldrich

392766

AD-mix-β

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64275

甲烷磺酰胺

Sigma-Aldrich

456705

(DHQ)₂AQN

Sigma-Aldrich

418978

(DHQ)₂Pyr

Sigma-Aldrich

418951

(DHQD)₂Pyr

Sigma-Aldrich

359343

氢化奎尼定

Sigma-Aldrich

107700

4-(二甲氨基)吡啶

品質等級

200

化驗

≥95%

光學活性

[α]22/D +336°, c = 1.2 in methanol

mp

178 °C (dec.) (lit.)

SMILES 字串

CC[C@@H]1CN2CCC1CC2[C@H](Oc3nnc(O[C@@H](C4CC5CCN4C[C@@H]5CC)c6ccnc7ccc(OC)cc67)c8ccccc38)c9ccnc%10ccc(OC)cc9%10

InChI

1S/C48H54N6O4/c1-5-29-27-53-21-17-31(29)23-43(53)45(35-15-19-49-41-13-11-33(55-3)25-39(35)41)57-47-37-9-7-8-10-38(37)48(52-51-47)58-46(44-24-32-18-22-54(44)28-30(32)6-2)36-16-20-50-42-14-12-34(56-4)26-40(36)42/h7-16,19-20,25-26,29-32,43-46H,5-6,17-18,21-24,27-28H2,1-4H3/t29-,30+,31-,32+,43-,44-,45-,46-/m1/s1

InChI 密鑰

YUCBLVFHJWOYDN-PPIALRKJSA-N

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一般說明

DHQ)₂PHAL is a modified cinchona alkaloid.

應用

Sharpless 不对称双羟基化的配体，用于由 (E,E)- 或 (E,Z)-1,3-二烯酸甲酯不对称制备 syn-3,5-羟基羧酸酯。

(DHQ)₂PHAL may be used in the following processes:

As a catalyst Asymmetric and chemoselective N-allylic alkylation of indoles with Morita-Baylis-Hillman carbonates to form pyrrolo[1,2-a]indole and pyrrolo[3,2,1-ij]quinoline derivatives.
As a ligand for the osmium catalyzed-Sharpless asymmetric dihydroxylation step of (S)-a-benzoyloxy carboxylic acids multistep synthesis.
As a ligand for the carbamate based asymmetric aminohydroxylation of styrene derivatives to form N-carbamate protected R-arylglycinols.

外觀

具有三取代 C=C 键的不饱和酯的不对称双羟基化。

象形圖

GHS07

訊號詞

Warning

危險聲明

H317

防範說明

P280 - P302 + P352

危險分類

Skin Sens. 1

儲存類別代碼

11 - Combustible Solids

水污染物質分類（WGK）

WGK 3

閃點（°F）

Not applicable

閃點（°C）

Not applicable

個人防護裝備

Eyeshields, Faceshields, Gloves, type N95 (US)

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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Troger 碱

From styrenes to enantiopure a-arylglycines in two steps.

Reddy KL and Sharpless KB.

Journal of the American Chemical Society, 120(6), 1207-1217 (1990)

Kapferer, Tobias; Brueckner, Reinhard

European Journal of Organic Chemistry, 9, 2119-2133 (2006)

Regioselective Oxidative Cleavage of Benzylidene Acetals: Synthesis of a-and ?-Benzoyloxy Carboxylic Acids.

Kumar PS, et al.

Angewandte Chemie (International Edition in English), 49(4), 804-807 (2010)

Chemoselective Asymmetric N-Allylic Alkylation of Indoles with Morita-Baylis-Hillman Carbonates.

Cui H-L, et al.

Angewandte Chemie (International Edition in English), 48(31), 5737-5740 (2009)

De novo synthesis of 2-substituted syn-1,3-diols via an iterative asymmetric hydration strategy.

Md Moinuddin Ahmed et al.

The Journal of organic chemistry, 71(20), 7741-7746 (2006-09-26)

The enantioselective syntheses of several protected 4-substituted syn-3,5-dihydroxy carboxylic esters have been achieved from the corresponding achiral (E,E)- or (E,Z)-1,3-dienoates. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form gamma-substituted delta-hydroxy-1-enoates. The resulting

商品

金鸡纳生物碱

不对称相转移催化（PTC）已被公认为是许多均相合成有机转化的“绿色”替代方法，并且已被广泛应用。合成修饰的金鸡纳生物碱是用于不对称PTC的典型手性有机催化剂。

Cinchona Alkaloids

Asymmetric phase-transfer catalysis (PTC) has been recognized as a “green” alternative to many homogeneous synthetic organic transformations, and has found widespread application. Synthetically modified cinchona alkaloids are typical chiral organocatalysts used in asymmetric PTC.

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(DHQ)₂PHAL