(+)-(4S,6R)-8-phenyloct-1-ene-4,6-diol | 135943-81-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+)-(4S,6R)-8-phenyloct-1-ene-4,6-diol
• 英文别名: (4S,6R)-8-phenyl-1-octene-4,6-diol；(3R,5S)-1-phenyloct-7-ene-3,5-diol
• CAS: 135943-81-6
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: LLHGYFRPJXDSHI-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(4S,6R)-8-phenyloct-1-ene-4,6-diol 在 ruthenium trichloride 、 sodium periodate 、 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 、 丙酮 为溶剂， 反应 3.0h， 生成 (4R,6R)-(+)-4-hydroxy-6-(2-phenylethyl)-tetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  Bouzbouz, Samir; Cossy, Janine, Tetrahedron Letters, 2000, vol. 41, # 18, p. 3362 - 3366

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-戊二酮,1,5-二氯 在 Ru2Cl4{2,2'-bis(diphenylphosphino)-1,1'-binaphthyl}2*N(C2H5)3 氢氧化钾 、 三氟化硼乙醚 、 氢气 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， -78.0~102.0 ℃ 、8.62 MPa 条件下， 反应 10.92h， 生成 (+)-(4S,6R)-8-phenyloct-1-ene-4,6-diol
  参考文献：
  名称：

  Optically pure 1,3-diols from (2R,4R)- and (2S,4S)-1,2:4,5-diepoxypentane

  摘要：

  Optically pure (> 97% ee) (2R,4R)-1,2:4,5-diepoxypentane (1) and its enantiomer can be prepared in three steps from 2,4-pentanedione without the need for chromatographic purification. Diepoxide 1 is an efficient precursor to a wide variety of optically pure syn and anti 1,3-diols. Reaction with excess nucleophile gives symmetric[GRAPHICS]anti 1,3-diols in good yield. Reaction with a slight excess of alkyllithium under Ganem's conditions gives the monoepoxides 5 in good yield. Addition of a second nucleophile to monoepoxide 5 gives asymmetric anti 1,3-diols. Mitsunobu inversion of monoepoxide 5 followed by addition of a second nucleophile gives syn 1,3-diols. Optically pure syn and anti 1,3-diols are available from diepoxide 1 in one to three steps and good overall yield.

  DOI：

  10.1021/jo00017a032

文献信息

• Enantioselective Synthesis of <i>syn</i>- and <i>anti-</i>1,3-Diols via Allyltitanation of Unprotected β-Hydroxyaldehydes
  作者：Samir BouzBouz、Janine Cossy

  DOI：10.1021/ol991349y

  日期：2000.2.1

  [GRAPHICS]syn or anti-1,3-diols units were synthesized with excellent diastereomeric excess from unprotected chiral beta-hydroxyaldehydes by using an enantioselective allyltitanation.
• US7534905B2
  申请人：——

  公开号：US7534905B2

  公开（公告）日：2009-05-19
• Optically pure 1,3-diols from (2R,4R)- and (2S,4S)-1,2:4,5-diepoxypentane
  作者：Scott D. Rychnovsky、George Griesgraber、Sam Zeller、Donald J. Skalitzky

  DOI：10.1021/jo00017a032

  日期：1991.8

  Optically pure (> 97% ee) (2R,4R)-1,2:4,5-diepoxypentane (1) and its enantiomer can be prepared in three steps from 2,4-pentanedione without the need for chromatographic purification. Diepoxide 1 is an efficient precursor to a wide variety of optically pure syn and anti 1,3-diols. Reaction with excess nucleophile gives symmetric[GRAPHICS]anti 1,3-diols in good yield. Reaction with a slight excess of alkyllithium under Ganem's conditions gives the monoepoxides 5 in good yield. Addition of a second nucleophile to monoepoxide 5 gives asymmetric anti 1,3-diols. Mitsunobu inversion of monoepoxide 5 followed by addition of a second nucleophile gives syn 1,3-diols. Optically pure syn and anti 1,3-diols are available from diepoxide 1 in one to three steps and good overall yield.
• Bouzbouz, Samir; Cossy, Janine, Tetrahedron Letters, 2000, vol. 41, # 18, p. 3362 - 3366
  作者：Bouzbouz, Samir、Cossy, Janine

  DOI：——

  日期：——