(3R)-4-exomethylene-3-[(R)-(hydroxy)(phenyl)methyl]tetrahydrofuran | 357915-02-7

• 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: (3R)-4-exomethylene-3-[(R)-(hydroxy)(phenyl)methyl]tetrahydrofuran
• 英文别名: (R)-[(3R)-4-methylideneoxolan-3-yl]-phenylmethanol
• CAS: 357915-02-7
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: SAFYPUKXDCRLNP-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (1S)-(-)-莰烷酰氯 、 (3R)-4-exomethylene-3-[(R)-(hydroxy)(phenyl)methyl]tetrahydrofuran 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到4-exomethylene-3-[(hydroxy)(phenyl)methyl]tetrahydrofuranyl (S)-(-)-camphanic ester
  参考文献：
  名称：

  Cycloisomerization of 1,6-enynes in organoaqueous medium: an efficient and eco-friendly access to furan derivatives. Synthesis of a key intermediate of podophyllotoxin

  摘要：

  The first cycloisomerization of enynes catalyzed by Pd(TPPTS)(3) catalyst in aqueous medium to give functionalized furans is described. This new reaction has been applied to the synthesis of podophyllotoxin analog. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00368-4
• 作为产物：
  描述：

  (E)-(3-(prop-2-yn-1-yloxy)prop-1-en-1-yl)benzene 在 palladium dichloride 4-二甲氨基吡啶 、 氢氧化钾 、 sodium triphenylphosphinosulfonate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 (3R)-4-exomethylene-3-[(R)-(hydroxy)(phenyl)methyl]tetrahydrofuran
  参考文献：
  名称：

  Cycloisomerization of 1,6-enynes in organoaqueous medium: an efficient and eco-friendly access to furan derivatives. Synthesis of a key intermediate of podophyllotoxin

  摘要：

  The first cycloisomerization of enynes catalyzed by Pd(TPPTS)(3) catalyst in aqueous medium to give functionalized furans is described. This new reaction has been applied to the synthesis of podophyllotoxin analog. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00368-4

文献信息

• Cycloisomerization of 1,6-enynes in organoaqueous medium: an efficient and eco-friendly access to furan derivatives. Synthesis of a key intermediate of podophyllotoxin
  作者：Jean-Christophe Galland、Sonia Dias、Monique Savignac、Jean-Pierre Genêt

  DOI：10.1016/s0040-4020(01)00368-4

  日期：2001.6

  The first cycloisomerization of enynes catalyzed by Pd(TPPTS)(3) catalyst in aqueous medium to give functionalized furans is described. This new reaction has been applied to the synthesis of podophyllotoxin analog. (C) 2001 Elsevier Science Ltd. All rights reserved.