(1S,5R)-2-(2-(benzyloxy)ethyl)-1,6-dimethylbicyclo[3.1.1]hept-2-ene | 934734-77-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,5R)-2-(2-(benzyloxy)ethyl)-1,6-dimethylbicyclo[3.1.1]hept-2-ene
• 英文别名: O-benzylnopol；(1S,5R)-6,6-dimethyl-2-(2-phenylmethoxyethyl)bicyclo[3.1.1]hept-2-ene
• CAS: 934734-77-7
• 化学式: C₁₈H₂₄O
• 分子量: 256.388
• InChiKey: VZTCOMJNYWLOOB-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,5R)-2-(2-(benzyloxy)ethyl)-1,6-dimethylbicyclo[3.1.1]hept-2-ene 在 N,N-二甲基乙酰胺 、 儿萘酚硼烷 、 苯磺酰基叠氮化物 、 反式-二叔丁基连二次硝酸酯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以78%的产率得到(1R,2R,3R,5S)-3-azido-2-[2-(benzyloxy)ethyl]-6,6-dimethylbicyclo[3.1.1]heptane
  参考文献：
  名称：

  A Radical Procedure for the Anti-Markovnikov Hydroazidation of Alkenes

  摘要：

  A one-pot procedure for the efficient hydroazidation of alkenes involving hydroboration with catecholborane followed by reaction with benzenesulfonyl azide in the presence of a radical initiator is described. The regioselectivity is controlled by the hydroboration step and corresponds in most cases to an anti-Markovnikov regioselectivity. This procedure is applicable to a wide range of alkenes and gives excellent results with 1,2-disubstituted and trisubstituted alkenes.

  DOI：

  10.1021/ja2054989
• 作为产物：
  描述：

  溴甲苯 、 (R)-(-)-nopol 在 sodium hydride 、 四丁基碘化铵 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 24.5h， 以87%的产率得到(1S,5R)-2-(2-(benzyloxy)ethyl)-1,6-dimethylbicyclo[3.1.1]hept-2-ene
  参考文献：
  名称：

  A Radical Procedure for the Anti-Markovnikov Hydroazidation of Alkenes

  摘要：

  A one-pot procedure for the efficient hydroazidation of alkenes involving hydroboration with catecholborane followed by reaction with benzenesulfonyl azide in the presence of a radical initiator is described. The regioselectivity is controlled by the hydroboration step and corresponds in most cases to an anti-Markovnikov regioselectivity. This procedure is applicable to a wide range of alkenes and gives excellent results with 1,2-disubstituted and trisubstituted alkenes.

  DOI：

  10.1021/ja2054989

文献信息

• Bromenium-Catalysed Tandem Ring Opening/Cyclisation of Vinylcyclopropanes and Vinylcyclobutanes: A Metal-Free [3+2+1]/[4+2+1] Cascade for the Synthesis of Chiral Amidines and Computational Investigation
  作者：Venkataraman Ganesh、Devarajulu Sureshkumar、Debasree Chanda、Srinivasan Chandrasekaran

  DOI：10.1002/chem.201103556

  日期：2012.9.24

  reaction has been further extended to vinylcyclobutane systems and involves a [4+2+1] cascade cyclisation with the same reagents. The versatility of the methodology has been demonstrated by careful choice of VCPs and VCBs to yield bicyclo[4.3.0]‐, ‐[4.3.1]‐ and ‐[4.4.0]amidines in enantiomerically pure form. On the basis of the experimental observations and DFT calculations, a reasonable mechanism has

  我们提出通过bromenium物种催化vinylcyclopropanes（VCP）的[3 + 2 + 1]级联环化的详细研究（BR δ +  X δ - ）原位产生的，其结果在手性二环脒在合成串联一锅操作。脒的形成涉及VCP厂商与溴开环X，然后与氯胺T进行Ritter型反应，并进行串联环化反应。该反应已进一步扩展至乙烯基环丁烷体系，并涉及使用相同试剂进行的[4 + 2 + 1]级联环化。通过仔细选择VCP和VCB可以产生对映体纯形式的双环[4.3.0]-，-[4.3.1]-和-[4.4.0] idine，证明了该方法的多功能性。在实验观察和DFT计算的基础上，提出了一种合理的机制来解释产物的形成和观察到的立体选择性。我们提出在环丙烷碳上存在π稳定的均碳正离子化是高立体选择性的原因。X）。从使用可极化连续体模型（PCM）溶剂化模型的固溶相（乙腈）计算中可以清楚地看出这一点，从中发现V
• A Radical Procedure for the Anti-Markovnikov Hydroazidation of Alkenes
  作者：Ajoy Kapat、Andreas König、Florian Montermini、Philippe Renaud

  DOI：10.1021/ja2054989

  日期：2011.9.7

  A one-pot procedure for the efficient hydroazidation of alkenes involving hydroboration with catecholborane followed by reaction with benzenesulfonyl azide in the presence of a radical initiator is described. The regioselectivity is controlled by the hydroboration step and corresponds in most cases to an anti-Markovnikov regioselectivity. This procedure is applicable to a wide range of alkenes and gives excellent results with 1,2-disubstituted and trisubstituted alkenes.

表征谱图