1-benzyloxy-1-[(2S)-oxiran-2-yl]-(1S)-heptane | 900783-34-8

• 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: 1-benzyloxy-1-[(2S)-oxiran-2-yl]-(1S)-heptane
• 英文别名: (S)-2-((S)-1-(benzyloxy)heptyl)oxirane；(2S)-2-[(1S)-1-phenylmethoxyheptyl]oxirane
• CAS: 900783-34-8
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: QGQNMJBOTBFIBV-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyloxy-1-[(2S)-oxiran-2-yl]-(1S)-heptane 在 Grubbs catalyst first generation 4-二甲氨基吡啶 、 四氯化钛 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 64.0h， 生成 (5R,6R,7E,10S)-5,6-dihydroxy-10-[(1'S)-1'-hydroxyheptyl]-3,4,5,6,9,10-hexahydro-2H-oxecin-2-one
  参考文献：
  名称：

  Stereoselective total synthesis of microcarpalide

  摘要：

  A stereoselective total synthesis of microcarpalide using ring-closing metathesis (RCM) as a key step is reported. L-Ascorbic acid was used as a chiral pool material for the construction of the olefinic alcohol and an asymmetric aldol reaction provided the chiral precursor for the synthesis of olefinic acid. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.03.024
• 作为产物：
  描述：

  3-benzyloxy-2-(4-methylphenylsulfonyloxy)-(2S,3S)-nonyl-4-methyl-1-benzenesulfonate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以91%的产率得到1-benzyloxy-1-[(2S)-oxiran-2-yl]-(1S)-heptane
  参考文献：
  名称：

  Enantiodivergent total synthesis of microcarpalide from l-tartaric acid

  摘要：

  Stereoselective approach for the synthesis of both enantiomers of bio-active decanolactone microcarpalide is described from L-tartaric acid. The synthesis of the key intermediates en route to the natural product is achieved from L-tartaric acid involving the elaboration of gamma-hydroxy amide derived from tartaric acid and ring opening of an epoxide derived from tartaric acid. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.102

文献信息

• Stereoselective total synthesis of microcarpalide
  作者：G.V.M. Sharma、Govardhan R. Cherukupalli

  DOI：10.1016/j.tetasy.2006.03.024

  日期：2006.4

  A stereoselective total synthesis of microcarpalide using ring-closing metathesis (RCM) as a key step is reported. L-Ascorbic acid was used as a chiral pool material for the construction of the olefinic alcohol and an asymmetric aldol reaction provided the chiral precursor for the synthesis of olefinic acid. (c) 2006 Elsevier Ltd. All rights reserved.
• Enantiodivergent total synthesis of microcarpalide from l-tartaric acid
  作者：Kavirayani R. Prasad、Kamala Penchalaiah

  DOI：10.1016/j.tet.2011.03.102

  日期：2011.6

  Stereoselective approach for the synthesis of both enantiomers of bio-active decanolactone microcarpalide is described from L-tartaric acid. The synthesis of the key intermediates en route to the natural product is achieved from L-tartaric acid involving the elaboration of gamma-hydroxy amide derived from tartaric acid and ring opening of an epoxide derived from tartaric acid. (C) 2011 Elsevier Ltd. All rights reserved.