(3aR,5R,6R,6aR)-6-methyl-5-[(E)-2-phenylethenyl]spiro[3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-2,1'-cyclohexane] | 602277-02-1

• 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: (3aR,5R,6R,6aR)-6-methyl-5-[(E)-2-phenylethenyl]spiro[3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-2,1'-cyclohexane]
• CAS: 602277-02-1
• 化学式: C₁₉H₂₄O₃
• 分子量: 300.398
• InChiKey: NEQOUBOOAHYUGF-HZPOSRMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aR,5R,6R,6aR)-6-methyl-5-[(E)-2-phenylethenyl]spiro[3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-2,1'-cyclohexane] 在 Amberlyst IR-120 (H+) resin 、 硫酸 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 17.0h， 生成 (3R,4R,5R)-3-Methoxy-4-methyl-5-((E)-styryl)-tetrahydro-furan-2-ol
  参考文献：
  名称：

  Carbohydrate-based synthesis of crocacin: stereoselective Heck reaction of carbohydrate 5,6-ene- and 5,6-yne-derivatives with aromatic halides

  摘要：

  The Heck reaction between a carbohydrate 5,6-ene derivative 9 and an aromatic halide exclusively gave rise to the beta-carbohydrate-substituted trans-styrene derivative 8; while the corresponding Wittig reaction produced a cis/trans mixture in which the cis-isomer predominated. The application of the Heck reaction is described to synthesize the intermediate 5, commonly used in the synthesis of members of the crocacin family. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01256-5
• 作为产物：
  描述：

  1,2:5,6-di-O-cyclohexylidene-α-D-ribo-3-hexofuranose-3-ulose 在 palladium diacetate 、 palladium on activated charcoal 硫酸 、 氢气 、 四丁基碘化铵 、 甲基磺酰氯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -10.0~110.0 ℃ 、344.74 kPa 条件下， 反应 41.5h， 生成 (3aR,5R,6R,6aR)-6-methyl-5-[(E)-2-phenylethenyl]spiro[3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-2,1'-cyclohexane]
  参考文献：
  名称：

  Carbohydrate-based synthesis of crocacin: stereoselective Heck reaction of carbohydrate 5,6-ene- and 5,6-yne-derivatives with aromatic halides

  摘要：

  The Heck reaction between a carbohydrate 5,6-ene derivative 9 and an aromatic halide exclusively gave rise to the beta-carbohydrate-substituted trans-styrene derivative 8; while the corresponding Wittig reaction produced a cis/trans mixture in which the cis-isomer predominated. The application of the Heck reaction is described to synthesize the intermediate 5, commonly used in the synthesis of members of the crocacin family. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01256-5

文献信息

• Carbohydrate-based synthesis of crocacin: stereoselective Heck reaction of carbohydrate 5,6-ene- and 5,6-yne-derivatives with aromatic halides
  作者：Mukund K. Gurjar、Tushar P. Khaladkar、Ramdas G. Borhade、A. Murugan

  DOI：10.1016/s0040-4039(03)01256-5

  日期：2003.7

  The Heck reaction between a carbohydrate 5,6-ene derivative 9 and an aromatic halide exclusively gave rise to the beta-carbohydrate-substituted trans-styrene derivative 8; while the corresponding Wittig reaction produced a cis/trans mixture in which the cis-isomer predominated. The application of the Heck reaction is described to synthesize the intermediate 5, commonly used in the synthesis of members of the crocacin family. (C) 2003 Elsevier Science Ltd. All rights reserved.