(2R)-endo-5-norbornene-2-methanol | 67671-06-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-endo-5-norbornene-2-methanol
• 英文别名: (2R)-2-endo-hydroxymethyl-5-norbornene；endo-(R)-norbornene-2-methanol；endo-5-norbornene-2-methanol；5-norbornene-2-methanol；5-norbornen-2-methanol；Bicyclo[2.2.1]hept-5-ene-2-methanol, (1R,2R,4R)-；[(1R,2R,4R)-2-bicyclo[2.2.1]hept-5-enyl]methanol
• CAS: 67671-06-1
• 化学式: C₈H₁₂O
• 分子量: 124.183
• InChiKey: LUMNWCHHXDUKFI-CSMHCCOUSA-N

物化性质

• 沸点：
  189.2±9.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2R)-endo-5-norbornene-2-methanol 以21%的产率得到
  参考文献：
  名称：

  NAKAZAKI M.; NAEMURA K.; KONDO Y., J. ORG. CHEM. , 1976, 41, NO 7, 1229-1233

  摘要：

  DOI：
• 作为产物：
  描述：

  [(3'aR,4S,7'S,7'aR)-2,2,2',2'-tetramethylspiro[1,3-dioxolane-4,6'-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran]-7'-yl] (1R,2R,4R)-bicyclo[2.2.1]hept-5-ene-2-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以61%的产率得到(2R)-endo-5-norbornene-2-methanol
  参考文献：
  名称：

  使用果糖二丙酮化物手性支架的高度非对映选择性Diels-Alder反应。

  摘要：

  DOI：

  10.1021/jo0002285

文献信息

• Rational Design of a New Chiral Lewis Acid Catalyst for Enantioselective Diels-Alder Reaction: Optically Active 2-Dichloroboryl-1,1′-binaphthyl
  作者：Kazuaki Ishihara、Kazato Inanaga、Shoichi Kondo、Miyuki Funahashi、Hisashi Yamamoto

  DOI：10.1055/s-1998-1860

  日期：1998.10

  A novel chiral aryldichloroborane catalyst bearing binaphthyl skeletons with axial chirality was developed as an asymmetric catalyst for the Diels-Alder reaction of dienes and α,β-unsaturated esters, and could be reused as the corresponding boronic acid. In addition, a new convenient method for preparing arylboronic acids from aryl alcohols is described.

  开发了一种具有轴手性的联萘骨架的新型手性二氯硼催化剂，用于二烯和α,β-不饱和酯的不对称Diels-Alder反应，并且可以作为相应的硼酸重复使用。此外，还描述了一种从芳基醇制备芳基硼酸的新方法。
• Immobilization of MacMillan Imidazolidinone as Mac-SILC and its Catalytic Performance on Sustainable Enantioselective Diels-Alder Cycloaddition
  作者：Hisahiro Hagiwara、Toshihiro Kuroda、Takashi Hoshi、Toshio Suzuki

  DOI：10.1002/adsc.200900865

  日期：2010.3.22

  (Mac‐SILC) in the pores of silica gel with the aid of an ionic liquid – 1‐butyl‐3‐methylimidazolium bis(trifluoromethylsulfonyl)imide. The heterogenized organocatalyst was utilized for the enantioselective Diels–Alder reaction of cyclopentadiene and cinnamaldehyde, recovered by simple filtration and subsequent evacuation, and repeatedly used up to six times in 81% average chemical yield, 87% ee for endo‐

  麦克米伦的咪唑啉酮催化剂作为负载型离子液体催化剂（Mac‐SILC）借助离子液体– 1-丁基-3-甲基咪唑双（三氟甲基磺酰基）酰亚胺固定在硅胶孔中。所述多相有机催化剂是用于环戊二烯与肉桂醛的对映选择性狄尔斯-阿尔德反应，回收通过简单过滤和随后的抽空，并重复使用多达六次在81％的平均化学产率，87％ee值用于内切-和80％ee值用于exo产品。Mac‐SILC对多种基材均有效。
• Transfer Hydrogenation of Aldehydes and Ketones with Isopropanol under Neutral Conditions Catalyzed by a Metal–Ligand Bifunctional Catalyst [Cp*Ir(2,2′-bpyO)(H₂O)]
  作者：Rongzhou Wang、Yawen Tang、Meng Xu、Chong Meng、Feng Li

  DOI：10.1021/acs.joc.7b03174

  日期：2018.2.16

  A Cp*Ir complex bearing a functional bipyridonate ligand [Cp*Ir(2,2′-bpyO)(H2O)] was found to be a highly efficient and general catalyst for transfer hydrogenation of aldehydes and chemoselective transfer hydrogenation of unsaturated aldehydes with isopropanol under neutral conditions. It was noteworthy that many readily reducible or labile functional groups such as nitro, cyano, ester, and halide

  发现带有功能联吡啶鎓配体[Cp * Ir（2,2'-bpyO）（H 2 O）]的Cp * Ir配合物是醛转移加氢和不饱和醛化学选择转移加氢的高效通用催化剂在中性条件下用异丙醇。值得注意的是，许多易还原或不稳定的官能团，例如硝基，氰基，酯和卤化物在反应条件下未发生任何变化。此外，该催化体系对于用异丙醇转移酮的氢化显示出高活性。值得注意的是，这项研究展示了金属-配体双功能催化剂在转移加氢方面的新潜力。
• APOPTOSIS-INDUCING AGENTS FOR THE TREATMENT OF CANCER AND IMMUNE AND AUTOIMMUNE DISEASES
  申请人：AbbVie Inc.

  公开号：US20130096121A1

  公开（公告）日：2013-04-18

  Disclosed are compounds which inhibit the activity of anti-apoptotic Bc1-xL proteins, compositions containing the compounds and methods of treating diseases during which is expressed anti-apoptotic Bc1-xL protein.

  揭示了抑制抗凋亡Bc1-xL蛋白活性的化合物，含有这些化合物的组合物以及治疗在其中表达抗凋亡Bc1-xL蛋白的疾病的方法。
• Copper-Catalyzed Oxysulfenylation of Enolates with Sodium Sulfinates: A Strategy To Construct Sulfenylated Cyclic Ethers
  作者：Yinglan Gao、Yang Gao、Xiaodong Tang、Jianwen Peng、Miao Hu、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/acs.orglett.6b00272

  日期：2016.3.4

  A new copper-catalyzed oxysulfenylation reaction of enolates with sodium sulfinates has been disclosed. A series of sulfenylated heterocycles including four- and seven-membered cyclic ether were obtained in mild to good yields. This reaction is proposed to go through a radical process, and the sulfur radical (RS•) may be a reactive species.

  已经公开了一种新的铜催化的烯醇盐与亚磺酸钠的氧磺酰化反应。以中等至良好的产率获得了一系列包括四元和七元环醚的亚磺酰基化杂环。建议该反应经过自由基过程，硫自由基（RS •）可能是反应性物质。