(5R,6R)-5,6-dihydroxy-6-phenyl-3-en-2-hexanone | 862307-56-0

• 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: (5R,6R)-5,6-dihydroxy-6-phenyl-3-en-2-hexanone
• 英文别名: (E,5R,6R)-5,6-dihydroxy-6-phenylhex-3-en-2-one
• CAS: 862307-56-0
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: BPJFMEAQYDWUBM-IDDPWSFUSA-N

物化性质

• 沸点：
  410.8±45.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.23
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (5R,6R)-5,6-dihydroxy-6-phenyl-3-en-2-hexanone 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以59.6%的产率得到(5R,6R)-5,6-diacetoxy-6-phenyl-3-en-2-hexanone
  参考文献：
  名称：

  Remote steric effect on the regioselectivity of Sharpless asymmetric dihydroxylation

  摘要：

  Studies on the regioselectivities for the Sharpless asymmetric dillydroxylation (AD) of conjugated dienoates, trienoates, dienones and dienamides are described. Excellent regioselectivities were obtained in straight chain dienoates, all trienoates, ketones damicles. The remote branched iso-propyl and tert-butyl groups of dienoates greatly lowered the normally excellent regiocontrol. This observation is rationalized in terms of substrate conformational changes, and the steric interaction between the branched methyl group of iso-propyl ortertbutyl groups and the ethyl group Oil the (DHQD)(2)PHAL ligand. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.119
• 作为产物：
  描述：

  (5R,6R)-5,6-diacetoxy-6-phenyl-3-en-2-hexanone 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以87%的产率得到(5R,6R)-5,6-dihydroxy-6-phenyl-3-en-2-hexanone
  参考文献：
  名称：

  Remote steric effect on the regioselectivity of Sharpless asymmetric dihydroxylation

  摘要：

  Studies on the regioselectivities for the Sharpless asymmetric dillydroxylation (AD) of conjugated dienoates, trienoates, dienones and dienamides are described. Excellent regioselectivities were obtained in straight chain dienoates, all trienoates, ketones damicles. The remote branched iso-propyl and tert-butyl groups of dienoates greatly lowered the normally excellent regiocontrol. This observation is rationalized in terms of substrate conformational changes, and the steric interaction between the branched methyl group of iso-propyl ortertbutyl groups and the ethyl group Oil the (DHQD)(2)PHAL ligand. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.119