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Merck
CN

265004

Sigma-Aldrich

(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

97%

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别名:
(-)-2,3-O-异亚丙基-1,1,4,4-四苯基-L-苏糖醇, (-)-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), (4R,5R)-4,5-双(二苯基羟甲基)-2,2-二甲基二氧戊环, 1,1,4,4-四苯基-2,3-O-异亚丙基-L-苏糖醇, TADDOL
经验公式(希尔记法):
C31H30O4
CAS号:
分子量:
466.57
Beilstein:
3657855
MDL编号:
UNSPSC代码:
12352005
PubChem化学物质编号:
NACRES:
NA.22

质量水平

检测方案

97%

旋光性

[α]19/D −62.6°, c = 1 in chloroform

mp

193-195 °C (lit.)

SMILES字符串

CC1(C)O[C@H]([C@@H](O1)C(O)(c2ccccc2)c3ccccc3)C(O)(c4ccccc4)c5ccccc5

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

InChI key

OWVIRVJQDVCGQX-VSGBNLITSA-N

应用

Hydrogen-bonding organocatalyst examined in terms of acidity, deprotonation enthalpies and hydrogen bonding

Catalyst involved in synthesis of cyclopropylamines via addition reactions of Grignard reagents to amides

Reactant or reagent involved in:
  • Enantioswitching of catalytic asymmetric hydroboration
  • Synthesis of derivative ligands for asymmetric hydroformylation of alkenes
  • Amide-directed catalytic asymmetric hydroboration of trisubstituted alkenes
  • Addition of deactivated alkyl Grignard reagents to aldehydes

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

法规信息

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Jung-Shen B Tai et al.
Physical review. E, 101(4-1), 042702-042702 (2020-05-20)
Chiral condensed matter systems, such as liquid crystals and magnets, exhibit a host of spatially localized topological structures that emerge from the medium's tendency to twist and its competition with confinement and field coupling effects. We show that the strength

商品

由Seebach小组开发的手性助剂TADDOL(α,α,α,α-四芳基-1,3-二氧戊环-4,5-二甲醇)在不对称合成中具有多种应用,包括从用作化学计量手性试剂或用于路易斯酸介导的反应,到在催化加氢和立体规则复分解聚合中发挥作用。

TADDOL chiral auxiliaries find diverse applications in asymmetric synthesis, catalysis, and polymerization.

TADDOLs demonstrate versatility in metal-catalyzed asymmetric reactions and as Brønsted acid organocatalysts in hetero-Diels–Alder reactions.

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