(+)-(S)-2-(benzyloxy)(1-2H)ethanol | 107653-66-7

• 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: (+)-(S)-2-(benzyloxy)(1-2H)ethanol
• 英文别名: (1S)-1-deuterio-2-phenylmethoxyethanol
• CAS: 107653-66-7
• 化学式: C₉H₁₂O₂
• 分子量: 153.185
• InChiKey: CUZKCNWZBXLAJX-UDMJAYEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(S)-2-(benzyloxy)(1-2H)ethanol 生成 (S)-2-hydroxy(1-2H)ethyl benzoate
  参考文献：
  名称：

  Hammerschmidt, Friedrich, Phosphorus and Sulfur and the Related Elements, 1987, vol. 30, p. 575 - 578

  摘要：

  DOI：
• 作为产物：
  描述：

  [1,1-²H₂]-2-benzyloxy-1-ethanol 在 乙醇 、 草酸氯化物 、 二甲基亚砜 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 45.83h， 生成 (+)-(S)-2-(benzyloxy)(1-2H)ethanol
  参考文献：
  名称：

  Hammerschmidt, Friedrich, Liebigs Annalen der Chemie, 1988, p. 955 - 960

  摘要：

  DOI：

文献信息

• Stereochemistry of the Conversion of 2-Phenoxyethanol into Phenol and Acetaldehyde byAcetobacterium sp.
  作者：Giovanna Speranza、Britta Mueller、Maximilian Orlandi、Carlo F. Morelli、Paolo Manitto、Bernhard Schink

  DOI：10.1002/hlca.200390212

  日期：2003.7

  The conversion of 2-phenoxyethanol to phenol and acetate by the anaerobic bacterium Acetobacterium sp. strain LuPhet1 proceeds through acetaldehyde with concomitant migration of a H-atom from C(1) to C(2) of the glycolic moiety. Separate feeding experiments with (R)- and (S)-2-phenoxy(1-2H)ethanol, prepared via chemoenzymatic syntheses, indicate that the H-atom involved in the 1,2-shift is the pro-S

  厌氧细菌醋杆菌将2-苯氧基乙醇转化为苯酚和乙酸盐。LuPhet1菌株通过乙醛行进，同时H原子从乙醇部分的C（1）迁移到C（2）。通过化学合成方法制备的（R）-和（S）-2-苯氧基（1-2 H）乙醇的单独进料实验表明，参与1,2移位的H原子是pro-S之一酒精功能的对映体对。
• Biosynthesis of natural products with a phosphorus-carbon bond. 7. Synthesis of [1,1-2H2]-, [2,2-2H2]-, (R)- and (S)-[1-2H1](2-hydroxyethyl)phosphonic acid and (R,S)-[1-2H1](1,2-dihydroxyethyl)phosphonic acid and incorporation studies into fosfomycin in Streptomyces fradiae
  作者：Friedrich Hammerschmidt、Hanspeter Kaehlig

  DOI：10.1021/jo00007a022

  日期：1991.3

  Nondeuteriated and deuteriated 2-(benzyloxy)ethanols (8a-c) were transformed into (2-hydroxyethyl)phosphonic acids (12a-c). 8c was prepared from dimethyl 2,3-O-isopropylidene-L-tartrate. 12b,c were fed to Streptomyces fradiae and were incorporated into fosfomycin (2), which was converted to amino phosphonic acid (-)-13. (-)-13 derived from 12b,c contained 42% and 34% deuterium, respectively. (1,2-Dihydroxyethyl)phosphonic acid ((+/-)-29) was not incorporated into fosfomycin. (S)- and (R)-(2-hydroxy[1-H-2-1]ethyl)phosphonic acids ((S)- and (R)-34) were prepared from (S)-2-(benzyloxy)[1-H-2-1]ethanol ((S)-30) and fed to S. fradiae. The deuterium of (R)-34 was lost, and the deuterium of (S)-34 was retained on incorporation into fosfomycin. The optical purity of (S)- and (R)-34 (84% and 86%, respectively) was determined by transformation to dimethyl ester and esterification with (+)-MTPA-Cl to afford 39b,c. 41 obtained from (S)-32 was identical with an authentic sample prepared from (S)-(2-amino[1-H-2-1]ethyl)phosphonic acid.
• Hammerschmidt, Friedrich, Liebigs Annalen der Chemie, 1992, # 6, p. 553 - 558
  作者：Hammerschmidt, Friedrich

  DOI：——

  日期：——
• Convenient Preparation of Chiral Primary Alcohols <i>via</i> Catalytic Asymmetric Reduction of Aldehydes Using Bu₃SnD
  作者：Gary E. Keck、Dhileepkumar Krishnamurthy

  DOI：10.1021/jo961593s

  日期：1996.1.1
• Hammerschmidt, Friedrich, Liebigs Annalen der Chemie, 1988, p. 961 - 964
  作者：Hammerschmidt, Friedrich

  DOI：——

  日期：——