(2S,3S)-3-(3-氟苯基)-2-(羟甲基)环氧乙烷 | 693220-51-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (2S,3S)-3-(3-氟苯基)-2-(羟甲基)环氧乙烷
• 英文名称: ((2S,3S)-3-(3-fluorophenyl)oxiran-2-yl)methanol
• 英文别名: (2S,3S)-3-(3-fluorophenyl)-2-(hydroxymethyl)oxirane；[(2S,3S)-3-(3-fluorophenyl)oxiran-2-yl]methanol
• CAS: 693220-51-8
• 化学式: C₉H₉FO₂
• 分子量: 168.168
• InChiKey: KDMCNZBHIWYKLQ-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-fluorocinnamaldehyde 在 sodium tetrahydroborate 、 (5R,6R)-6-((tert-butyldiphenylsilyl)oxy)-1-azaspiro[4.4]nonane 作用下， 以 甲醇 、 水 为溶剂， 反应 48.67h， 生成 (2S,3S)-3-(3-氟苯基)-2-(羟甲基)环氧乙烷
  参考文献：
  名称：

  Asymmetric epoxidation of α,β-unsaturated aldehydes catalyzed by a spiro-pyrrolidine-derived organocatalyst

  摘要：

  The asymmetric epoxidation of alpha,beta-unsaturated aldehydes, catalyzed by a spiro-pyrrolidine (SPD)-derived organocatalyst, has been accomplished with good diastereoselectivities (up to dr >20:1) and with high to excellent enantioselectivities (up to 99% ee). (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.02.009

文献信息

• Large-Scale Synthesis of a Selective Inhibitor of the Norepinephrine Transporter: Mechanistic Aspects of Conversion of Indolinone Diol to Indolinone Aminoalcohol and Process Implications
  作者：Asaf Alimardanov、Alexander Gontcharov、Antonia Nikitenko、Anita W. Chan、Zhixian Ding、Mousumi Ghosh、Mahmut Levent、Panolil Raveendranath、Jianxin Ren、Maotang Zhou、Paige E. Mahaney、Casey C. McComas、Joseph Ashcroft、John R. Potoski

  DOI：10.1021/op900141r

  日期：2009.9.18

  Development of a scalable synthesis of WAY-315193 is described. Use of LiHMDS as a base and Ti(O-i-Pr)(4) as a Lewis acid was optimal for efficient and reproducible addition of indolinone anion to epoxyalcohol. Conversion of indolinone diol to indolinone aminoalcohol was achieved via monotosylation-methylamination. The possibility of selective formation of the amidine side product, as well as its utilization for alternative selective preparation of the target aminoalcohol, was demonstrated.
• 3-Aryloxy/thio-2,3-substituted propanamines and their use in inhibiting serotonin and norepinephrine reuptake
  申请人：Boulet Louis Serge

  公开号：US20060173035A1

  公开（公告）日：2006-08-03

  There is provided a compound of formula (I) wherein A is selected from —O— and —S—; X is selected from phenyl optionally substituted with up to 5 substituents each independently selected from halo, C 1 -C 4 alkyl and C 1 -C 4 alkoxy, thienyl optionally substituted with up to 3 substituents each independently selected from halo and C 1 -C 4 alkyl, and C 2 -C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 8 cycloalkyl and C 4 -C 8 cycloalkylalkyl, each of which may be optionally substituted with up to 3 substituents each independently selected from halo, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl-S(O) n — where n is 0, 1 or 2, —CF 3 , —CN and —CONH 2 ; Y is selected from phenyl, naphthyl, dihydrobenzothienyl, benzothiazolyl, benzoisothiazolyl, quinolyl, isoquinolyl, naphthyridyl, thienopyridyl, indanyl, 1,3-benzodioxolyl, benzothienyl, indolyl and benzofuranyl, each of which may be optionally substituted with up to 4 or, where possible, up to 5 substituents each independently selected from halo, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl-S(O) n — where n is 0, 1 or 2, nitro, acetyl, —CF 3 , —SCF 3 and cyano; and when Y is indolyl it may be substituted or further substituted by an N-substituent selected from C 1 -C 4 alkyl; Z is selected from OR 3 or F, wherein R 3 is selected from H, C 1 -C 6 alkyl and phenyl C 1 -C 6 alkyl; R 1 and R 2 are each independently H or C 1 -C 4 alkyl; and pharmaceutically acceptable salts thereofwith the proviso that when Y is optionally substituted phenyl or optionally substituted 1,3-benzodioxolyl and Z is OR 3 and X is optionally substituted phenyl then A is —S—.
• US7410996B2
  申请人：——

  公开号：US7410996B2

  公开（公告）日：2008-08-12
• Asymmetric epoxidation of α,β-unsaturated aldehydes catalyzed by a spiro-pyrrolidine-derived organocatalyst
  作者：Ming-Hui Xu、Yong-Qiang Tu、Jin-Miao Tian、Fu-Min Zhang、Shao-Hua Wang、Shi-Heng Zhang、Xiao-Ming Zhang

  DOI：10.1016/j.tetasy.2016.02.009

  日期：2016.4

  The asymmetric epoxidation of alpha,beta-unsaturated aldehydes, catalyzed by a spiro-pyrrolidine (SPD)-derived organocatalyst, has been accomplished with good diastereoselectivities (up to dr >20:1) and with high to excellent enantioselectivities (up to 99% ee). (C) 2016 Elsevier Ltd. All rights reserved.