CAS 93379-48-7|[(4R,5R)-5-(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]diphenylmethanol|TADDOL|(4R,5R)-2,2-Dimethyl-alpha,alpha,alpha',alpha'-tetraphenyldioxolane-4,5-dimethanol|(-)-2,3-O-...

General Information

Structure

Molecular Formula

C₃₁H₃₀O₄

Molecular Mass

466.5675

Exact Mass

466.21440944

Charge

InChI

InChI=1S/C31H30O4/c1-29(2)34-27(30(32,23-15-7-3-8-16-23)24-17-9-4-10-18-24)28(35-29)31(33,25-19-11-5-12-20-25)26-21-13-6-14-22-26/h3-22,27-28,32-33H,1-2H3/t27-,28-/m1/s1

InChIKey

OWVIRVJQDVCGQX-VSGBNLITSA-N

Canonic Smiles

OC(c1ccccc1)(c1ccccc1)[C@@H]1OC(O[C@H]1C(c1ccccc1)(c1ccccc1)O)(C)C

Isomeric Smiles

O1[C@@H](C(c2ccccc2)(c2ccccc2)O)[C@@H](OC1(C)C)C(c1ccccc1)(c1ccccc1)O

Calculated Properties

JChem

Acid pKa

12.106078

H Acceptors

H Donor

LogD (pH = 5.5)

5.8206005

LogD (pH = 7.4)

5.820592

Log P

5.8206005

Molar Refractivity

136.6576

Polarizability

53.904915

Polar Surface Area

58.92

Rotatable Bonds

Lipinski's Rule of Five

false

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

IUPAC name

[(4R,5R)-5-(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]diphenylmethanol

Synonyms

TADDOL(4R,5R)-2,2-Dimethyl-alpha,alpha,alpha',alpha'-tetraphenyldioxolane-4,5-dimethanol(-)-2,3-O-Isopropylidene-1,1,4,4-tetrphenyl-L-threitol(4R,5R)-2,2-二甲基-α,α,α′,α′-四苯基-1,3-二氧戊环-4,5-二甲醇1,1,4,4-四苯基-2,3-O-异亚丙基-L-苏糖醇(4R,5R)-4,5-双(二苯基羟甲基)-2,2-二甲基二氧戊环1,1,4,4-Tetraphenyl-2,3-O-isopropylidene-L-threitol(-)-2,3-O-Isopropylidene-1,1,4,4-tetraphenyl-L-threitol(4R,5R)-4,5-Bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane(4R,5R)-2,2-Dimethyl-α,α,α′,α′-tetraphenyldioxolane-4,5-dimethanol(-)-反式-α,α′-(2,2-二甲基-1,3-二氧戊环-4,5-二基)双(二苯基甲醇)(-)-2,3-O-异亚丙基-1,1,4,4-四苯基-L-苏糖醇(-)-trans-α,α′-(2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol)

IUPAC Traditional name

[(4R,5R)-5-(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]diphenylmethanol

Names and Identifiers

Registration numbers

MDL Number

MFCD00064467

CAS Number

93379-48-7

PubChem SID

162078939248815692485604824893437

PubChem CID

2725026

Beilstein Number

3657855

Registration numbers

Properties

Safety Information

Storage Warning

Irritant

German water hazard class

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

MSDS Link

Download link

Product Information

97%

≥97.0% (sum of enantiomers, HPLC)

C31H30O4

purum

Physical Property

193-195 °C(lit.)

192-195 °C

[α]19/D -62.6°, c = 1 in chloroform

[α]20/D -67±2°, c = 1% in chloroform

Properties

Related Proteins

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Molecular Spectra

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Molecule Details

Sigma Aldrich

D1431

Application
用作不对称催化剂、1光学拆分试剂2以及核磁共振波谱法中的手性位移试剂。3

265004

Packaging
1 g in glass bottle
Application
Hydrogen-bonding organocatalyst examined in terms of acidity, deprotonation enthalpies and hydrogen bonding1Catalyst involved in synthesis of cyclopropylamines via addition reactions of Grignard reagents to amides2Reactant or reagent involved in:
• Enantioswitching of catalytic asymmetric hydroboration3
• Synthesis of derivative ligands for asymmetric hydroformylation of alkenes4
• Amide-directed catalytic asymmetric hydroboration of trisubstituted alkenes5
• Addition of deactivated alkyl Grignard reagents to aldehydes6

Molecule Details

References

PubChem Literature

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References

Bioactivity

PubChem BioAssay

Bioactivity