(2S)-8-phenylmethoxyoct-4-yn-2-ol | 912365-53-8

• 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: (2S)-8-phenylmethoxyoct-4-yn-2-ol
• CAS: 912365-53-8
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: GHCBIYYQBZGPLW-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-8-phenylmethoxyoct-4-yn-2-ol 在 palladium on activated charcoal 咪唑 、 锂硼氢 、 三氟甲磺酸二丁硼 、 camphor-10-sulfonic acid 、 氢气 、 N,N-二异丙基乙胺 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 甲苯 为溶剂， 反应 48.5h， 生成 methyl (E)-3-[(4S,5R)-5-[(6S)-6-[tert-butyl(diphenyl)silyl]oxyheptyl]-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate
  参考文献：
  名称：

  First synthesis and determination of the absolute stereochemistry of iso-cladospolide-B and cladospolides-B and C

  摘要：

  The syntheses of iso-cladospolide-B, cladospolide-B and cladospolide-C are reported with 4S,5S,11S-configuration. Of the three stereogenic centres, the C-4/C-5 vic-diol was created by Evans aldol condensation, while the C-11 stereocentre was created by Jacobsen's method. The synthesis of cladospolides 1-3 defined the absolute stereochemistry of these natural products. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.044
• 作为产物：
  描述：

  5-benzyloxy-1-pentyne 在 R,R-Jacobsen's catalyst copper(l) iodide 、 lithium aluminium tetrahydride 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 39.0h， 生成 (2S)-8-phenylmethoxyoct-4-yn-2-ol
  参考文献：
  名称：

  First synthesis and determination of the absolute stereochemistry of iso-cladospolide-B and cladospolides-B and C

  摘要：

  The syntheses of iso-cladospolide-B, cladospolide-B and cladospolide-C are reported with 4S,5S,11S-configuration. Of the three stereogenic centres, the C-4/C-5 vic-diol was created by Evans aldol condensation, while the C-11 stereocentre was created by Jacobsen's method. The synthesis of cladospolides 1-3 defined the absolute stereochemistry of these natural products. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.044

文献信息

• First synthesis and determination of the absolute stereochemistry of iso-cladospolide-B and cladospolides-B and C
  作者：G.V.M. Sharma、K. Laxmi Reddy、J. Janardhan Reddy

  DOI：10.1016/j.tetlet.2006.07.044

  日期：2006.9

  The syntheses of iso-cladospolide-B, cladospolide-B and cladospolide-C are reported with 4S,5S,11S-configuration. Of the three stereogenic centres, the C-4/C-5 vic-diol was created by Evans aldol condensation, while the C-11 stereocentre was created by Jacobsen's method. The synthesis of cladospolides 1-3 defined the absolute stereochemistry of these natural products. (c) 2006 Elsevier Ltd. All rights reserved.