(+/-)-6-benzyloxy-3-hydroxyhexanoic acid ethyl ester | 158094-56-5

• 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: (+/-)-6-benzyloxy-3-hydroxyhexanoic acid ethyl ester
• 英文别名: Ethyl 3-hydroxy-6-phenylmethoxyhexanoate
• CAS: 158094-56-5
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: IHQNLZTWALGZEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-6-benzyloxy-3-hydroxyhexanoic acid ethyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (+)-6-benzyloxy-3-hydroxyhexanoic acid
  参考文献：
  名称：

  Total synthesis of the piperidinol alkaloid (−)-(2R,3R,6S)-cassine

  摘要：

  A highly efficient, flexible and diastereoselective route to all-cis-2,6-disubstituted 3-piperidinols has been accomplished. The key component of the synthesis is a chiral beta-hydroxyester, which was obtained by lipase catalyzed kinetic resolution. Based on this starting material, diastereoselective alkylation of its dianion, Curtius rearrangement to a 2-oxazolidinone, Grignard reaction to introduce the side-chain and conversion of the aliphatic 2-oxazolidinone into a 3-piperidinol by imine cyclization lead to the exemplary total synthesis of naturally occurring (-)-(2R,3R,6S)-cassine. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(96)00537-x
• 作为产物：
  描述：

  4-苯基甲氧基-丁醛 、 溴乙酸乙酯 在 铜 、 锌 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 以89%的产率得到(+/-)-6-benzyloxy-3-hydroxyhexanoic acid ethyl ester
  参考文献：
  名称：

  Total synthesis of the piperidinol alkaloid (−)-(2R,3R,6S)-cassine

  摘要：

  A highly efficient, flexible and diastereoselective route to all-cis-2,6-disubstituted 3-piperidinols has been accomplished. The key component of the synthesis is a chiral beta-hydroxyester, which was obtained by lipase catalyzed kinetic resolution. Based on this starting material, diastereoselective alkylation of its dianion, Curtius rearrangement to a 2-oxazolidinone, Grignard reaction to introduce the side-chain and conversion of the aliphatic 2-oxazolidinone into a 3-piperidinol by imine cyclization lead to the exemplary total synthesis of naturally occurring (-)-(2R,3R,6S)-cassine. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(96)00537-x

文献信息

• Total synthesis of the piperidinol alkaloid (−)-(2R,3R,6S)-cassine
  作者：Jörg Oetting、Jens Holzkamp、Hartmut H. Meyer、Axel Pahl

  DOI：10.1016/s0957-4166(96)00537-x

  日期：1997.2

  A highly efficient, flexible and diastereoselective route to all-cis-2,6-disubstituted 3-piperidinols has been accomplished. The key component of the synthesis is a chiral beta-hydroxyester, which was obtained by lipase catalyzed kinetic resolution. Based on this starting material, diastereoselective alkylation of its dianion, Curtius rearrangement to a 2-oxazolidinone, Grignard reaction to introduce the side-chain and conversion of the aliphatic 2-oxazolidinone into a 3-piperidinol by imine cyclization lead to the exemplary total synthesis of naturally occurring (-)-(2R,3R,6S)-cassine. (C) 1997 Elsevier Science Ltd. All rights reserved.