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254606

Sigma-Aldrich

(S)-(-)-2,2-二甲基-1,3-二氧戊环-4-羧酸甲酯

96%

同義詞:

α,β-异亚丙基-L-甘油酸甲酯, 2,3-O-异亚丙基-L-甘油酸甲酯, 甲基α,β-异亚丙基-L-甘油酸酯

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About This Item

經驗公式(希爾表示法):
C7H12O4
CAS號碼:
分子量::
160.17
Beilstein:
4292352
MDL號碼:
分類程式碼代碼:
12352005
PubChem物質ID:
NACRES:
NA.22

品質等級

化驗

96%

形狀

liquid

光學活性

[α]20/D −8.5°, c = 1.5 in acetone

光學純度

ee: ≥96.0% (GLC)

折射率

n20/D 1.425 (lit.)

bp

84-86 °C/15 mmHg (lit.)

密度

1.106 g/mL at 25 °C (lit.)

SMILES 字串

COC(=O)[C@@H]1COC(C)(C)O1

InChI

1S/C7H12O4/c1-7(2)10-4-5(11-7)6(8)9-3/h5H,4H2,1-3H3/t5-/m0/s1

InChI 密鑰

DOWWCCDWPKGNGX-YFKPBYRVSA-N

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應用

(−)-Methyl (S)-2,2-dimethyl-1,3-dioxolane-4-carboxylate can be used:
  • As a chiral building block to make the key tetrahydrofuran subunit of (−)-gymnodimine, a marine algal toxin.
  • To prepare an enedione by reacting with dimethyl methylphosphonate, BuLi, and phenylglyoxal, which in turn is used to synthesize cyclopentenone derivatives.
  • As a starting material for the preparation of (S)-4,5-dihydroxy-2,3-pentanedione (DPD), a precursor for autoinducer (AI)-2 in bacteria.

儲存類別代碼

10 - Combustible liquids

水污染物質分類(WGK)

WGK 3

閃點(°F)

172.4 °F - closed cup

閃點(°C)

78 °C - closed cup

個人防護裝備

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


分析證明 (COA)

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Annulation of 2-Oxoalkylidenetriphenylphosphoranes with enediones: A one-step synthesis of substituted cyclopentenones
Kitano H, et al.
Synthesis, 2002(06), 0739-0744 (2002)
James D White et al.
The Journal of organic chemistry, 72(5), 1717-1728 (2007-02-01)
Two principal subunits of the marine algal toxin (-)-gymnodimine were synthesized. A trisubstituted tetrahydrofuran representing C10-C18 of the toxin was prepared via a highly stereoselective iodine-mediated cyclization of an acyclic alkene bearing a bis-2,6-dichlorobenzyl (DCB) ether. The formation of a

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