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Merck
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重要文件

392723

Sigma-Aldrich

(DHQ)2PHAL

≥95%

同義詞:

氢化奎宁 1,4-(2,3-二氮杂萘)二醚

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About This Item

經驗公式(希爾表示法):
C48H54N6O4
CAS號碼:
分子量::
778.98
Beilstein:
5475677
MDL號碼:
分類程式碼代碼:
12352005
PubChem物質ID:
NACRES:
NA.22

品質等級

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

Exclamation mark

訊號詞

Warning

危險聲明

防範說明

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)


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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

文章

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。

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.

相關內容

The Sharpless Lab pursues useful new reactivity and general methods for selectively controlling chemical reactions.

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