1-{(2R,5R)-5-[(1R,2E)-1-hydroxy-5-methyl-2,4-hexadienyl]-tetrahydrofuran-2-yl}-propan-2-one | 537007-15-1

• 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: 1-{(2R,5R)-5-[(1R,2E)-1-hydroxy-5-methyl-2,4-hexadienyl]-tetrahydrofuran-2-yl}-propan-2-one
• 英文别名: 1-[(2R,5R)-5-[(1R,2E)-1-hydroxy-5-methylhexa-2,4-dienyl]oxolan-2-yl]propan-2-one
• CAS: 537007-15-1
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: AICGGLFQIVQPFS-HMYILGODSA-N

物化性质

• 沸点：
  373.9±12.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 1-{(2R,5R)-5-[(1R,2E)-1-hydroxy-5-methyl-2,4-hexadienyl]-tetrahydrofuran-2-yl}-propan-2-one 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以93%的产率得到
  参考文献：
  名称：

  Absolute stereochemistry of amphidinolide C: synthesis of C-1–C-10 and C-17–C-29 segments

  摘要：

  Two of each diastereomers of the C-1-C-10 and C-17-C-29 segments of amphidinolide C (1) were synthesized. Comparing the H-1 NMR chemical shifts of its MTPA esters with those of linear methyl ester of 1, the absolute configurations at C-7, C-8, C-20, C-23, and C-24 in amphidinolide C (1) were confirmed to be all R. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00142-x
• 作为产物：
  描述：

  Benzoic acid 2-benzenesulfonyl-4-methyl-1-{(S)-triethylsilanyloxy-[(2R,5R)-5-(2-triethylsilanyloxy-ethyl)-tetrahydro-furan-2-yl]-methyl}-pent-3-enyl ester 在 disodium hydrogenphosphate 、 sodium amalgam 、 pyridine-SO3 complex 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 8.0h， 生成 1-{(2R,5R)-5-[(1R,2E)-1-hydroxy-5-methyl-2,4-hexadienyl]-tetrahydrofuran-2-yl}-propan-2-one
  参考文献：
  名称：

  Absolute stereochemistry of amphidinolide C: synthesis of C-1–C-10 and C-17–C-29 segments

  摘要：

  Two of each diastereomers of the C-1-C-10 and C-17-C-29 segments of amphidinolide C (1) were synthesized. Comparing the H-1 NMR chemical shifts of its MTPA esters with those of linear methyl ester of 1, the absolute configurations at C-7, C-8, C-20, C-23, and C-24 in amphidinolide C (1) were confirmed to be all R. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00142-x

文献信息

• Absolute stereochemistry of amphidinolide C: synthesis of C-1–C-10 and C-17–C-29 segments
  作者：Takaaki Kubota、Masashi Tsuda、Jun'ichi Kobayashi

  DOI：10.1016/s0040-4020(03)00142-x

  日期：2003.3

  Two of each diastereomers of the C-1-C-10 and C-17-C-29 segments of amphidinolide C (1) were synthesized. Comparing the H-1 NMR chemical shifts of its MTPA esters with those of linear methyl ester of 1, the absolute configurations at C-7, C-8, C-20, C-23, and C-24 in amphidinolide C (1) were confirmed to be all R. (C) 2003 Elsevier Science Ltd. All rights reserved.