2-[(2R,5R)-5-Methyl-5-(2,3,4,9-tetrahydro-1H-β-carbolin-1-ylmethyl)-tetrahydro-furan-2-yl]-propan-2-ol | 270923-48-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 2-[(2R,5R)-5-Methyl-5-(2,3,4,9-tetrahydro-1H-β-carbolin-1-ylmethyl)-tetrahydro-furan-2-yl]-propan-2-ol
• 英文别名: 2-[(2R,5R)-5-methyl-5-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-ylmethyl)oxolan-2-yl]propan-2-ol
• CAS: 270923-48-3
• 化学式: C₂₀H₂₈N₂O₂
• 分子量: 328.455
• InChiKey: CBUYBOAOZDHZEU-HMEKMZBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  57.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(2R,5R)-5-Methyl-5-(2,3,4,9-tetrahydro-1H-β-carbolin-1-ylmethyl)-tetrahydro-furan-2-yl]-propan-2-ol 在 palladium on activated charcoal 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以57%的产率得到(+)-cyclocapitelline
  参考文献：
  名称：

  The total synthesis of chrysotricine

  摘要：

  Geraniol was converted, using Sharpless oxidations as key steps, into the chiral tuans-tri-substituted tetrahydrofuran 10, from which chrysotricine was synthesized in 16 steps (1.1% overall yield). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00146-5
• 作为产物：
  描述：

  2-[(2R,5R)-5-(2-Benzyloxy-ethyl)-5-methyl-tetrahydro-furan-2-yl]-propan-2-ol 在 palladium on activated charcoal 草酰氯 、 氢气 、 二甲基亚砜 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-[(2R,5R)-5-Methyl-5-(2,3,4,9-tetrahydro-1H-β-carbolin-1-ylmethyl)-tetrahydro-furan-2-yl]-propan-2-ol
  参考文献：
  名称：

  The total synthesis of chrysotricine

  摘要：

  Geraniol was converted, using Sharpless oxidations as key steps, into the chiral tuans-tri-substituted tetrahydrofuran 10, from which chrysotricine was synthesized in 16 steps (1.1% overall yield). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00146-5

文献信息

• Oxidative cyclization of tertiary pentenol derivatives forming 2,5,5-trisubstituted THF rings and the total synthesis of cyclocapitelline
  作者：Geoffrey A. Phillips、Cory Palmer、Andrew C. Stevens、Mathew L. Piotrowski、Daryl S.R. Dekruyf、Brian L. Pagenkopf

  DOI：10.1016/j.tetlet.2015.09.064

  日期：2015.10

  The synthesis of 2,5,5-trisubstituted tetrahydrofuran rings was accomplished via the Mukaiyama aerobic oxidative cyclization of tertiary 5-pentenols employing the Co(nmp)2 catalyst. A variety of THFs were formed in moderate to good yield and diastereoselectivity. The method developed herein was successfully applied to an enantioselective total synthesis of cyclocapitelline.

  2,5,5-三取代的四氢呋喃环的合成是通过使用Co（nmp）2催化剂对5-戊烯叔叔醇进行Mukaiyama有氧氧化环化来完成的。以中等至良好的产率和非对映选择性形成了各种THF。本文开发的方法已成功地应用于环己内酯的对映选择性全合成。
• The total synthesis of chrysotricine
  作者：Jing-Xin Zhang、Guang-Xing Wang、Ping Xie、Shu-Feng Chen、Xiao-Tian Liang

  DOI：10.1016/s0040-4039(00)00146-5

  日期：2000.3

  Geraniol was converted, using Sharpless oxidations as key steps, into the chiral tuans-tri-substituted tetrahydrofuran 10, from which chrysotricine was synthesized in 16 steps (1.1% overall yield). (C) 2000 Elsevier Science Ltd. All rights reserved.