(1R,2s)-2-(异丙基氨基)-1,2-二苯乙醇 | 222555-57-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: (1R,2s)-2-(异丙基氨基)-1,2-二苯乙醇
• 英文名称: (1R,2S)-2-(isopropylamino)-1,2-diphenylethanol
• 英文别名: (1R,2S)-1,2-diphenyl-2-(propan-2-ylamino)ethanol
• CAS: 222555-57-9
• 化学式: C₁₇H₂₁NO
• mdl: MFCD00798212
• 分子量: 255.36
• InChiKey: ILABSMRKFLZNPK-DLBZAZTESA-N

物化性质

• 沸点：
  378.1±9.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.294
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2s)-2-(异丙基氨基)-1,2-二苯乙醇 在 4-二甲氨基吡啶 作用下， 以 甲苯 为溶剂， 反应 32.5h， 生成 N-[(1S,2R)-2-diphenylphosphanyloxy-1,2-diphenylethyl]-N-methylpropan-2-amine
  参考文献：
  名称：

  Easily accessible chiral amino-phosphinite ligands for highly enantioselective palladium-mediated allylic alkylation

  摘要：

  Palladium-catalyzed asymmetric allylic alkylation of 1,3-diplienyl-2-propenyl acetate with the dimethyl malonate-BSA-LiOAc system has been successfully carried out in the presence of easily prepared new chiral amino-phosphinite ligands such as 3b and 3c to result in good yields and excellent enantioselectivities of up to 95%, e.e. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00204-5
• 作为产物：
  描述：

  (1R,2S)-2-氨基-1,2-二苯基乙醇 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 (1R,2s)-2-(异丙基氨基)-1,2-二苯乙醇
  参考文献：
  名称：

  Easily accessible chiral amino-phosphinite ligands for highly enantioselective palladium-mediated allylic alkylation

  摘要：

  Palladium-catalyzed asymmetric allylic alkylation of 1,3-diplienyl-2-propenyl acetate with the dimethyl malonate-BSA-LiOAc system has been successfully carried out in the presence of easily prepared new chiral amino-phosphinite ligands such as 3b and 3c to result in good yields and excellent enantioselectivities of up to 95%, e.e. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00204-5
• 作为试剂：
  描述：

  四氢-4-羟基-2H-吡喃-4-甲腈 在 吡啶 、 N,N-diethylaniline borane 、 三氟甲磺酸 、 二异丁基氢化铝 、 (1R,2s)-2-(异丙基氨基)-1,2-二苯乙醇 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 L-脯氨酸 、 三氯氧磷 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 甲醇 、 溶剂黄146 、 甲苯 为溶剂， 反应 7.0h， 生成 (S)-9-hydroxy-4-isopropyl-7,7-dimethyl-2',3',5',6,6',7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]-3-one 、 (R)-9-hydroxy-4-isopropyl-7,7-dimethyl-2',3',5',6,6',7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]-3-one
  参考文献：
  名称：

  高效进入多环胆固醇酯转移蛋白抑制剂的实用对映选择性合成方法。

  摘要：

  已经开发了手性多环胆固醇酯转移蛋白（CETP）抑制剂1的有效对映选择性合成。通过开发改良的Hantzsch型反应以制备位阻吡啶环，利用新型BIBOP-氨基吡啶衍生的Ru配合物对位酮6进行对映选择性氢化，有效的ICl促进内酯形成，以及通过合成IHC促进内酯的形成，使该合成大规模可行。BF 3介导的氢化过程，用于非对映选择性的乳糖醇还原。这种有效的途径已成功扩展规模，以产生具有挑战性的CETP候选药物1的多千克数量。

  DOI：

  10.1021/ol501833g

文献信息

• Indium-mediated Barbier-type allylation of aldehydes as a convenient method for the highly enantioselective synthesis of homoallylic alcohols
  作者：Lacie C. Hirayama、Soya Gamsey、Daniel Knueppel、Derek Steiner、Kelly DeLaTorre、Bakthan Singaram

  DOI：10.1016/j.tetlet.2005.01.169

  日期：2005.3

  enantioselective allylation of both aromatic and aliphatic aldehydes using commercially available (1S,2R)-(+)-2-amino-1,2-diphenylethanol as a chiral auxiliary. Using only two equivalents of allyl bromide, excellent yields and very good to excellent enantioselectivities are obtained. To our knowledge, the enantioselectivities reported herein are the highest obtained for indium-promoted allylations of carbonyl

  我们报告了使用市售（1 S，2 R）-（+）-2-氨基-1,2-二苯乙醇作为手性助剂的铟介导的芳香族和脂肪族醛的Barbier型对映选择性烯丙基化的一般方法。仅使用两个当量的烯丙基溴，可获得优异的产率和非常好的至优异的对映选择性。据我们所知，本文报道的对映选择性是由铟促进的羰基化合物的烯丙基化所获得的。
• New Methods and Reagents in Organic Synthesis 89. Studies on Reaction Conditions and New Entry to Chiral Ligands in the Chiral Lithium Amide-Mediated Enantioselective Aldol Reaction.
  作者：Akira ANDO、Toshiaki TATEMATSU、Takayuki SHIOIRI

  DOI：10.1248/cpb.39.1967

  日期：——

  Reaction conditions for the enantioselective aldol reaction of 2, 2-dimethyl-3-pentanone (3) and benzaldehyde using the chiral lithium amide 1b as a chiral auxiliary were thoroughly investigated. All three procedures, that is, (1) the combined use of lithium diisopropylamide and the chiral lithium amide 1b, (2) the use of an excess of the chiral lithium amide 1b, and (3) the regeneration of the chiral lithium amide 1b, afforded the aldol 4 in about 90% yield and 70% enantiomeric excess (ee). Investigation of the effects of solvent by utilizing 1-naphthaldehyde revealed that in tetrahydrofuran, (S, S)-aldol 5 of 77% ee was obtained as the major product, while in ether (R, R)-5 became the major isomer (38% ee). Furthermore, addition of hexamethylphosphoric triamide caused a dramatic change of stereoselectivity, and (S, S)-5 of 70% ee was obtained in ether with 20 eq of hexamethylphosphoric triamid. The aldol 4 of 74% ee was obtained when the new chiral lithium amide 6b was used.

  对使用手性锂胺1b作为手性辅助剂的2,2-二甲基-3-戊酮（3）和苯甲醛的立体选择性醛醇反应的反应条件进行了彻底的研究。所有三种程序，即（1）使用二异丙基锂胺和手性锂胺1b的组合，（2）过量使用手性锂胺1b，和（3）再生手性锂胺1b，都能以约90%的产率和70%的旋光纯度（ee）得到醛醇产物4。通过利用1-萘甲醛研究溶剂影响，发现在四氢呋喃中，主要产物是旋光纯度为77%的（S, S）-醛醇5，而在乙醚中，主要异构体变为旋光纯度为38%的（R, R）-5。此外，加入六甲基磷酸三胺会导致立体选择性的显著变化，在乙醚中加入20 eq的六甲基磷酸三胺，得到了旋光纯度为70%的（S, S）-5。当使用新手性锂胺6b时，得到了旋光纯度为74%的醛醇4。
• New 1-amino-1,2-diphenylethanols as ligands for the enantioselective addition of alkyllithiums to benzaldehyde
  作者：Michael Schön、Reto Naef

  DOI：10.1016/s0957-4166(98)00473-x

  日期：1999.1

  In the presence of equimolar amounts of lithium alkoxides derived from N-substituted 2-amino-1,2-diphenylethanols, alkyllithium reagents add to benzaldehyde to furnish optically active secondary alcohols with enantiomeric excesses of up to 86%. The best results were obtained using the N-isopropyl-N-methyl substituted amin-oalcohol. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Easily accessible chiral amino-phosphinite ligands for highly enantioselective palladium-mediated allylic alkylation
  作者：Guoshu Chen、Xin Li、Haile Zhang、Liuzhu Gong、Aiqiao Mi、Xin Cui、Yaozhong Jiang、Michael C.K. Choi、Albert S.C. Chan

  DOI：10.1016/s0957-4166(02)00204-5

  日期：2002.5

  Palladium-catalyzed asymmetric allylic alkylation of 1,3-diplienyl-2-propenyl acetate with the dimethyl malonate-BSA-LiOAc system has been successfully carried out in the presence of easily prepared new chiral amino-phosphinite ligands such as 3b and 3c to result in good yields and excellent enantioselectivities of up to 95%, e.e. (C) 2002 Published by Elsevier Science Ltd.