(1S,2R)-<1-2H>-1-phenylpropan-2-ol | 135637-09-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2R)-<1-2H>-1-phenylpropan-2-ol
• 英文别名: (1S,2R)-1-phenyl(1-2H1)propan-2-ol；(1S,2R)-[1-2H]-1-phenylpropan-2-ol；(1S,2R)-1-deuterio-1-phenylpropan-2-ol
• CAS: 135637-09-1
• 化学式: C₉H₁₂O
• 分子量: 137.186
• InChiKey: WYTRYIUQUDTGSX-ITUCVEAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,2R)-<1-2H>-1-phenylpropan-2-ol 在 吡啶 、 sodium hydroxide 、 Dimethylglyoxime 、 氢气 、 cobalt(II) chloride 作用下， 反应 9.5h， 生成
  参考文献：
  名称：

  Deniau, Jean; Van Duong, Kiem Nguyen; Merienne, Claude, Bulletin de la Societe Chimique de France, 1983, vol. 2, # 5-6, p. 180 - 184

  摘要：

  DOI：
• 作为产物：
  描述：

  (1R,2S)-1-苯基-1,2-丙二醇 在 吡啶 、 lithium aluminium deuteride 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 (1S,2R)-<1-2H>-1-phenylpropan-2-ol
  参考文献：
  名称：

  The mode of bakers' yeast transformation of 3-chloropropiophenone and related ketones. Synthesis of (2S)-[2-2H]propiophenone, (R)-fluoxetine, and (R)- and (S)-fenfluramine

  摘要：

  Yeast treatment of 3-chloropropiophenone (2) affords the expected (1S)-3-chloro-1-phenylpropan-1-ol (3) as well as ca. 30% of propiophenone (5). The conversion of 2 into 5 is accompanied by formal elimination of hydrochloric acid, followed by yeast saturation of the double bond of the intermediate phenyl vinyl ketone (4). Monodeuteriopropiophenone formed via yeast treatment from alpha,alpha-dideuterio-3-chloropropiophenone (8) was shown to possess the 2S configuration 10 by conversion into [2-H-2]-(1R,2S)-1-phenylpropan-1-ol (13), whose stereochemistry was assigned by comparison of its NMR properties with those of the [2-H-2]-(1S,2S) diastereoisomer 19 synthesized from yeast-generated (1R,2S)-1-phenylpropane-1,2-diol (15). Whereas product 3 is converted into (R)-fluoxetine (31), 2S alcohol 24, obtained in the yeast reduction of the ketone 22 is transformed into (R)-fenfluramine (29) and into its enantiomer (26).

  DOI：

  10.1021/jo00021a011

文献信息

• Conformational analysis of amphetamine in solution based on unambiguous assignment of the diastereotopic benzylic protons in the 1H NMR spectra
  作者：Alexandros Makriyannis、James Knittel

  DOI：10.1016/s0040-4039(01)82999-3

  日期：1981.1

  The erythro- and threo-amphetamine-β-d diastereomers were synthesized and used for the unambiguous assignment of the diastereotopic benzylic protons and the measurement of vicinal 1H-1H coupling constants which were used to determine the distribution of rotamers around the central cα-cβ bond in the side chain.

  所述赤-和苏-amphetamine-β-d非对映体合成的，并用于非对映异构苄型质子的明确分配和邻位的测定1个H- 1个，其被用于确定旋转异构体的围绕中心C中的分布ħ偶合常数侧链中的α - cβ键。
• Efficient Control of the Stereoselectivity in Reactions of 2-Oxy-Substituted Benzylic Radicals
  作者：Nadira Moufid、Philippe Renaud、Carla Hassler、Bernd Giese

  DOI：10.1002/hlca.19950780422

  日期：1995.6.28

  The stereoselectivity in reactions of 2-oxy-substituted radicals of type B was investigated. As expected, minimization of allylic 1,3-strain was the major controlling factor. Under standard conditions, only a modest level of stereoselectivity was observed. E.g., deuteration of the benzylated radical (R1 = benzyl) gave diastereoisomer ratios ≤ 2:1. Use of a bulky protective group on the O-atom (R1 =

  研究了B型2-氧取代基在反应中的立体选择性。如预期的那样，最小化烯丙基1，3-菌株是主要的控制因素。在标准条件下，仅观察到适度的立体选择性。例如，苄基化的基团的氘代（R 1＝苄基）给出的非对映异构体比率≤2∶1。在O原子上使用庞大的保护基（R 1 =（t -Bu）Ph 2Si）略微提高了选择性（比率4.1：1）。但是，当用庞大的甲基铝双（酚盐）衍生物（甲基铝双[2,6-二（叔丁基-丁基] -4-甲基苯氧基]（MAD）和甲基铝双（2,6-二苯基苯氧基）（MAPH））。
• Lee, Yunmi; Hoveyda, Amir H., Journal of the American Chemical Society, 2009, vol. 131, p. 3160 - 3161
  作者：Lee, Yunmi、Hoveyda, Amir H.

  DOI：——

  日期：——
• MACHKOVA Z.; ZAVADA J., COLLECT. CZECH. CHEM. COMMUN., 1981, 46, NO 4, 833-849
  作者：MACHKOVA Z.、 ZAVADA J.

  DOI：——

  日期：——