(2R)-N-[(1S)-3,6-dihydro-2H-pyran-2-ylmethanoyl]bornane-10,2-sultam | 445027-91-8

• 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: (2R)-N-[(1S)-3,6-dihydro-2H-pyran-2-ylmethanoyl]bornane-10,2-sultam
• 英文别名: [(2S)-3,6-dihydro-2H-pyran-2-yl]-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]methanone；[(2S)-3,6-dihydro-2H-pyran-2-yl]-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]methanone
• CAS: 445027-91-8
• 化学式: C₁₆H₂₃NO₄S
• 分子量: 325.429
• InChiKey: ABNILAOHJMBCCQ-OQMKEHIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R)-N-[(1S)-3,6-dihydro-2H-pyran-2-ylmethanoyl]bornane-10,2-sultam 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 以60%的产率得到[(2S)-3,6-二氢-2H-吡喃-2-基]甲醇
  参考文献：
  名称：

  Highly diastereoselective hetero-Diels–Alder reaction of buta-1,3-diene with N-glyoxyloyl-(2R)-bornane-10,2-sultam: an efficient synthesis of homochiral (S)-3-[2-{(methylsulfonyl)oxy}ethoxy]-4-(triphenylmethoxy)-1-butanol methanesulfonate

  摘要：

  The influence of Lewis acid on the diastereo selectivity of [4+2] cycloaddition of buta-1,3-diene to N-glyoxyloyl-(2R)-bornane-10,2-sultam was investigated and high levels of asymmetric induction were achieved. (S)-3-[2- (Methylsulfonyl)oxy}ethoxyl-4-(triphenylmethoxy)-1-butanol methanesulfonate were synthesized in 15% overall yield, applying as a crucial step the above-mentioned [4+2] cycloaddition catalyzed by ZnBr2. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00746-2
• 作为产物：
  描述：

  (2R)-N-[(2S)-2-allyloxypent-4-enoyl]bornane-10,2-sultam 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到(2R)-N-[(1S)-3,6-dihydro-2H-pyran-2-ylmethanoyl]bornane-10,2-sultam
  参考文献：
  名称：

  Synthesis of enantiomerically pure divinyl- and diallylcarbinols

  摘要：

  经乙烯基或烯丙基金属化合物处理，酰化噁唑啉酮和降冰片烷砜可裂解为二乙烯基和二烯丙基甲醇。制备二乙烯基甲醇时，酰化降冰片烷砜为首选起始原料；而在制备二烯丙基甲醇时，酰化噁唑啉酮和降冰片烷砜同样适用。

  DOI：

  10.1039/b200976e

文献信息

• Stereochemistry of the Diels–Alder reaction at high pressure: diastereo- and enantioselective [4+2]cycloaddition of buta-1,3-diene to glyoxylic acid derivatives catalysed by (salen) chromium(III) complexes
  作者：Małgorzata Kosior、Piotr Kwiatkowski、Monika Asztemborska、Janusz Jurczak

  DOI：10.1016/j.tetasy.2005.06.032

  日期：2005.9

  High-pressure [4+2]cycloadditions of buta-1,3-diene 1 to chiral 2a–c and achiral 7a–c glyoxylates, in the presence of (salen) chromium(III) complexes 5 and 6, were studied. The influence of such chiral Lewis acids on diastereoselectivity or enantioselectivity of the cycloaddition was investigated; a moderate asymmetric induction for both diastereo- and enantioselective variants of the cycloaddition

  在（salen）铬（III）配合物5和6存在下，研究了丁醇-1,3-二烯1与手性2a – c和非手性7a – c乙醛酸酯的高压[4 + 2]环加成反应。研究了这种手性路易斯酸对环加成反应的非对映选择性或对映选择性的影响。观察到对环加成的非对映体和对映体选择性变体有中等程度的不对称诱导（分别高达58％的de和71％的ee）。
• <b>Diastereoselective Reaction of Buta-1,3-diene with Chiral Derivatives of Glyoxylic­ Acid: Effective Route to Optically Pure 2-Substituted 3,6-Dihydro-2</b> <b><i>H</i></b> <b>-pyrans</b>
  作者：Janusz Jurczak、Magorzata Kosior、Monika Asztemborska

  DOI：10.1055/s-2003-44372

  日期：——

  The influence of Lewis acids on the diastereoselectivity of [4+2] cycloaddition of buta-1,3-diene (4) to N-glyoxyloyl-(2R)-bornane-10,2-sultam (6a) and (R)-8-phenylmenthyl glyoxylate (6b) was investigated and found to have high levels of asymmetric induction. The highest asymmetric induction (ca. 100% de) was obtained for the reaction of 4 with 6b carried out in toluene and in the presence of chelating

  路易斯酸对 1,3-二烯 (4) 与 N-乙醛酰-(2R)-冰片烷-10,2-磺胺 (6a) 和 (R)- 的 [4+2] 环加成反应的非对映选择性的影响研究了 8-苯基薄荷基乙醛酸 (6b)，发现其具有高水平的不对称诱导。在甲苯中和螯合路易斯酸（SnCl 4 、TiCl 4 ）存在下，4 与 6b 的反应获得了最高的不对称感应（约 100% de）。
• Synthesis of enantiomerically pure divinyl- and diallylcarbinols
  作者：Bernd Schmidt、Holger Wildemann

  DOI：10.1039/b200976e

  日期：2002.4.9

  Acylated oxazolidinones and bornane sultams can be cleaved to divinyl- and diallylcarbinols by treatment with vinyl- or allylmetal compounds. For the preparation of divinylcarbinols, acylated bornane sultams are the starting materials of choice, while for the preparation of diallylcarbinols acylated oxazolidinones and bornane sultams work equally well.

  经乙烯基或烯丙基金属化合物处理，酰化噁唑啉酮和降冰片烷砜可裂解为二乙烯基和二烯丙基甲醇。制备二乙烯基甲醇时，酰化降冰片烷砜为首选起始原料；而在制备二烯丙基甲醇时，酰化噁唑啉酮和降冰片烷砜同样适用。
• Highly diastereoselective hetero-Diels–Alder reaction of buta-1,3-diene with N-glyoxyloyl-(2R)-bornane-10,2-sultam: an efficient synthesis of homochiral (S)-3-[2-{(methylsulfonyl)oxy}ethoxy]-4-(triphenylmethoxy)-1-butanol methanesulfonate
  作者：Małgorzata Kosior、Małgorzata Malinowska、Julita Jóźwik、Jean-Claude Caille、Janusz Jurczak

  DOI：10.1016/s0957-4166(02)00746-2

  日期：2003.1

  The influence of Lewis acid on the diastereo selectivity of [4+2] cycloaddition of buta-1,3-diene to N-glyoxyloyl-(2R)-bornane-10,2-sultam was investigated and high levels of asymmetric induction were achieved. (S)-3-[2- (Methylsulfonyl)oxy}ethoxyl-4-(triphenylmethoxy)-1-butanol methanesulfonate were synthesized in 15% overall yield, applying as a crucial step the above-mentioned [4+2] cycloaddition catalyzed by ZnBr2. (C) 2003 Elsevier Science Ltd. All rights reserved.