(S)-(-)-3-amino-2-phenylpropan-1-ol | 127298-25-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-(-)-3-amino-2-phenylpropan-1-ol
• 英文别名: (S)-(-)-2-amino-3-phenylpropanol；(S)-3-amino-2-phenylpropan-1-ol；(2S)-3-amino-2-phenylpropan-1-ol
• CAS: 127298-25-3
• 化学式: C₉H₁₃NO
• 分子量: 151.208
• InChiKey: DIVZNCUPEGZSEI-VIFPVBQESA-N

物化性质

• 沸点：
  292.4±20.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(-)-3-amino-2-phenylpropan-1-ol 在 sodium hydroxide 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 水 为溶剂， 反应 13.0h， 生成 (S)-(-)-3-N-methylamino-2-phenylpropan-1-ol
  参考文献：
  名称：

  化学酶促合成1,2-和1,3-氨基醇及其在用硼烷对映选择性还原苯乙酮和抗苯乙酮肟甲基醚中的用途。

  摘要：

  以生物转化为关键步骤，对映选择性地合成了新的手性氨基醇。它们用作苯乙酮和相应的抗肟甲基醚的对映选择性硼烷还原中的配体。

  DOI：

  10.1016/s0040-4020(01)80959-5
• 作为产物：
  描述：

  2-苯基-1,3-丙二醇 在 lithium aluminium tetrahydride 、 sodium azide 、 甲基三辛基氯化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成 (S)-(-)-3-amino-2-phenylpropan-1-ol
  参考文献：
  名称：

  化学酶促合成1,2-和1,3-氨基醇及其在用硼烷对映选择性还原苯乙酮和抗苯乙酮肟甲基醚中的用途。

  摘要：

  以生物转化为关键步骤，对映选择性地合成了新的手性氨基醇。它们用作苯乙酮和相应的抗肟甲基醚的对映选择性硼烷还原中的配体。

  DOI：

  10.1016/s0040-4020(01)80959-5

文献信息

• Syntheses of Pyrrolo- and Indoloisoquinolinones by Intramolecular Cyclizations of 1-(2-Arylethyl)-5-benzotriazolylpyrrolidin-2-ones and 3-Benzotriazolyl-2-(2-arylethyl)-1-isoindolinones
  作者：Alan R. Katritzky、Shamal Mehta、Hai-Ying He

  DOI：10.1021/jo001273f

  日期：2001.1.1

  1-alpha]isoquinolin-3(2H)-ones 17a,b, 17d,e, and 5,12b-dihydroisoindolo[1,2-alpha]isoquinolin-8(6H)-ones 22a-e were prepared by intramolecular cyclizations of 1-(2-arylethyl)-5-benzotriazolyl-pyrrolidin-2-ones 15a,b, 15d,e, and 3-benzotriazolyl-2-(2-arylethyl)-1-isoindolinones 20a-e, respectively, in the presence of titanium chloride. Products from chiral amines were obtained with stereoselectivities of > or

  1,5,6,10b-四氢吡咯并[2,1-α]异喹啉-3（2H）-一个17a，b，17d，e和5,12b-二氢异吲哚并[1,2-α异喹啉-8（6H） ）-酮22a-e是通过1-（2-芳基乙基）-5-苯并三唑基-吡咯烷-2-酮15a，b，15d，e和3-苯并三唑基-2-（2-芳基乙基）-的分子内环化制备的1-异吲哚啉酮20a-e分别在氯化钛存在下。获得手性胺的产物，其立体选择性≥94％。
• Synthesis of (S)-N-Boc-3-Amino-2-Arylpropanol from Optically Active β-Amino Esters
  作者：Monique Calmès、Françoise Escale、Jean Martinez

  DOI：10.1055/s-2001-15237

  日期：——

  The reduction of various (αS,3"R)-pantolactonyl-2-aryl-3-phthalimidopropanoates 3 followed by an acidic treatment and direct N-Boc protection afforded the corresponding (S)-N-Boc-3-amino-2-arylpropanols 4 in good yield and without loss of the optical purity.

  各种 (αS,3"R)-泛内酯基-2-芳基-3-邻苯二甲酰亚胺丙酸酯 3 的还原，然后进行酸性处理和直接 N-Boc 保护，得到相应的 (S)-N-Boc-3-amino- 2-芳基丙醇4的收率良好且不损失光学纯度。
• Synthesis and in vitro evaluation of novel 2,6,9-trisubstituted purines acting as cyclin-dependent kinase inhibitors
  作者：Michel Legraverend、Odile Ludwig、Emile Bisagni、Sophie Leclerc、Laurent Meijer、Nicole Giocanti、Ramin Sadri、Vincent Favaudon

  DOI：10.1016/s0968-0896(99)00064-4

  日期：1999.7

  Novel C-2, C-6, N-9 trisubstituted purines derived from the olomoucine/roscovitine lead structure were synthesized and evaluated for their ability to inhibit starfish oocyte CDK1/cyclin B, neuronal CDK5/p35 and erk1 kinases in purified extracts. Structure-activity relationship studies showed that increased steric bulk at N-9 reduces the inhibitory potential whereas substitution of the aminoethanol C-2 side chain by various groups of different size (methyl, propyl, butyl, phenyl, benzyl) only slightly decreases the activity when compared to (R)-roscovitine. Optimal inhibitory activity against CDK5, CDK1 and CDK2, with IC50 values of 0.16, 0.45 and 0.65 mu M, respectively, was obtained with compound 21 containing a (2R)-pyrrolidin-2-yl-methanol substituent at the C-2 and a 3-iodobenzylamino group at the C-6 of the purine. Compound 21 proved cytotoxic against human tumor HeLa cells (LD50 = 6.7 mu M versus 42.7 mu M for olomoucine, 24-h contact). Furthermore, unlike olomoucine, compound 21 was effective upon short exposure (LD50 = 25.3 mu M, 2-h contact). The available data suggest that the affinity for CDKs and the cytotoxic potential of the drugs are inter-related. However, no straightforward cell cycle phase specificity of the cytotoxic response to 21 was observed in synchronized HeLa cells. With the noticeable exception of pronounced lengthening of the S-phase transit by 21 applied during early-S in synchronized HeLa cells, and in striking contrast with earlier reports on studies using plant or echinoderm cells, olomoucine and compound 21 were unable to reversibly arrest cell cycle progression in asynchronous growing HeLa cells. Some irreversible block in G1 and G2 phase occurred at high olomoucine concentration, correlated with induced cell death. Moreover, chronic exposure to lethal doses of compound 21 resulted in massive nuclear fragmentation, evocative of mitotic catastrophe with minor amounts of apoptosis only. It was also found that olomoucine and compound 21 reversibly block the intracellular uptake of nucleosides with high efficiency. (C) 1999 Elsevier Science Ltd. All rights reserved.
• US5045567A
  申请人：——

  公开号：US5045567A

  公开（公告）日：1991-09-03
• Chemo-enzymatic synthesis of 1,2- and 1,3- amino-alcohols and their use in the enantioselective reduction of acetophenone and anti-acetophenone oxime methyl ether with borane.
  作者：Eric Didier、Bernard Loubinoux、Gerardo H. Ramos Tombo、Grety Rihs

  DOI：10.1016/s0040-4020(01)80959-5

  日期：1991.1

  New chiral amino-alcohols were enantioselectively synthesized using biotransformations as the key steps. They were used as ligand in the enantioselective borane reduction of acetophenone and of the corresponding anti oxime methyl ether.

  以生物转化为关键步骤，对映选择性地合成了新的手性氨基醇。它们用作苯乙酮和相应的抗肟甲基醚的对映选择性硼烷还原中的配体。