(2R,5R)-2-[2-(1,3-dioxolan-2-yl)ethyl]-1-allyl-5-(benzyloxy)-2-vinylpiperidine | 1395687-62-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (2R,5R)-2-[2-(1,3-dioxolan-2-yl)ethyl]-1-allyl-5-(benzyloxy)-2-vinylpiperidine
• 英文别名: (2R,5R)-2-[2-(1,3-dioxolan-2-yl)ethyl]-2-ethenyl-5-phenylmethoxy-1-prop-2-enylpiperidine
• CAS: 1395687-62-3
• 化学式: C₂₂H₃₁NO₃
• 分子量: 357.493
• InChiKey: CWKPNUKFNOTNBK-IFMALSPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,5R)-2-[2-(1,3-dioxolan-2-yl)ethyl]-1-allyl-5-(benzyloxy)-2-vinylpiperidine 在 盐酸 、 草酰氯 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 3.67h， 生成 (1S,5S,6R)-2-allyl-1-vinyl-2-azaspiro[bicyclo[3.3.1]nonane-4,2'-[1,3]dioxolan]-6-ol
  参考文献：
  名称：

  Enantioselective Total Syntheses of (−)-FR901483 and (+)-8-epi-FR901483

  摘要：

  The enantioselective total syntheses of the potent immunosuppressant FR901483 (1) and its 8-epimer (47) have been accomplished. Our approach features the use of building block 6 as the chiron, the application of the one-pot amide reductive bis-alkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diaster-eoselective intramolecular aldol reaction to build the bridged ring, and RCM to form the 3-pyrrolin-2-one ring.

  DOI：

  10.1021/jo302362b
• 作为产物：
  描述：

  (R)-1-allyl-3-benzyloxy-2,6-piperidinedione 在 sodium tetrahydroborate 、 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.25h， 生成 (2R,5R)-2-[2-(1,3-dioxolan-2-yl)ethyl]-1-allyl-5-(benzyloxy)-2-vinylpiperidine 、 (2S,5R)-2-[2-(1,3-dioxolan-2-yl)ethyl]-1-allyl-5-(benzyloxy)-2-vinylpiperidine
  参考文献：
  名称：

  Enantioselective Total Syntheses of (−)-FR901483 and (+)-8-epi-FR901483

  摘要：

  The enantioselective total syntheses of the potent immunosuppressant FR901483 (1) and its 8-epimer (47) have been accomplished. Our approach features the use of building block 6 as the chiron, the application of the one-pot amide reductive bis-alkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diaster-eoselective intramolecular aldol reaction to build the bridged ring, and RCM to form the 3-pyrrolin-2-one ring.

  DOI：

  10.1021/jo302362b

文献信息

• A Formal Enantioselective Total Synthesis of FR901483
  作者：Hao-Hua Huo、Hong-Kui Zhang、Xiao-Er Xia、Pei-Qiang Huang

  DOI：10.1021/ol302165d

  日期：2012.9.21

  A formal enantioselective total synthesis of the potent immunosuppressant FR901483 (1) has been accomplished. Our approach features the use of chiron 6 as the starting material, the application of the one-pot amide reductive bisalkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diastereoselective intramolecular aldol reaction to build the bridged ring, and ring closing metathesis to form the 3-pyrrolin-2-one ring.
• Enantioselective Total Syntheses of (−)-FR901483 and (+)-8-<i>epi</i>-FR901483
  作者：Hao-Hua Huo、Xiao-Er Xia、Hong-Kui Zhang、Pei-Qiang Huang

  DOI：10.1021/jo302362b

  日期：2013.1.18

  The enantioselective total syntheses of the potent immunosuppressant FR901483 (1) and its 8-epimer (47) have been accomplished. Our approach features the use of building block 6 as the chiron, the application of the one-pot amide reductive bis-alkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diaster-eoselective intramolecular aldol reaction to build the bridged ring, and RCM to form the 3-pyrrolin-2-one ring.