borneol

• 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: borneol
• 英文别名: (1S,2S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: DTGKSKDOIYIVQL-DXEWVWIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  borneol 在 N-(2-iodylphenyl)glutarylamide supported on amonomethylpolystyrene resin 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 (1S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
  参考文献：
  名称：

  Development of new recyclable reagents and catalytic systems based on hypervalent iodine compounds

  摘要：

  Recent advances in the development of polymer-supported iodine(V) oxidants, recyclable monomeric hypervalent iodine(III) reagents and catalytic systems based on hypervalent iodine compounds are discussed. These efficient and environmentally friendly reagents and catalysts are particularly useful for oxidative transformations of alcohols to carbonyl compounds and for oxidations at the benzylic position.

  DOI：

  10.1016/j.mencom.2010.06.001
• 作为产物：
  描述：

  (+/-)-bornyl acetate 在 水 作用下， 反应 120.0h， 生成 borneol
  参考文献：
  名称：

  Spirodela oligorrhiza对外消旋单萜醇乙酸酯的对映特异性水解

  摘要：

  摘要 外消旋薄荷醇、冰片、反式-2-羟基-反式-二氢频醇、顺式-2-羟基-反式-二氢频醇和反式-2-羟基-顺式-二氢频松的乙酸酯在寡根螺旋藻培养物中发生对映特异性水解。R 醇的形成速度比 S 快。缺光会抑制前两种醋酸酯的水解。

  DOI：

  10.1016/0031-9422(88)80667-8

文献信息

• A new class of stereoselective reducing agents, potassium 9-alkyl-9-boratabicyclo [3.3.1]nonanes
  作者：Jin Soon Cha、Mal Sook Yoon、Young Shick Kim、Kwang Woo Lee

  DOI：10.1016/0040-4039(88)85337-1

  日期：1988.1

  A new class of reducing agents, potassium 9-alkyl-9-boratabicyclo[3.3.1]nonanes (K 9-R-9-BBNHs) was examined its stereoselectivity toward cyclic ketones. Among these, K 9-TB-9-BBNH reveals the most favorable stereoselectivity, comparable to that by lithium trisiamylborohydride at 0°C.

  研究了一类新的还原剂，9-烷基-9-硼双双环[3.3.1]壬烷钾（K 9-R-9-BBNHs）对环酮的立体选择性。其中，K 9-TB-9-BBNH具有最有利的立体选择性，与0℃下的三唾液酸硼氢化锂可比。
• Copper(II) Exchanged Cation Exchange Resin: Useful Activator in the Reduction of Ketones
  作者：A. Sarkar、B. R. Rao、B. Ram

  DOI：10.1080/00397919308009781

  日期：1993.2

  Abstract A copper(II) exchanged cation exchange resin has been used as support for reduction of ketones with sodium borohydride. Supported Cu(II) ions activate the reduction of ketones to a large extent and control the stereochemistry of reductions of cyclic ketones resulting in preponderance of equatorial alcohol in most cases.

  摘要 铜（II）交换的阳离子交换树脂已被用作硼氢化钠还原酮的载体。负载的 Cu(II) 离子在很大程度上激活了酮的还原，并控制了环酮还原的立体化学，导致在大多数情况下赤道醇占优势。
• Kim, Sunggak; Lee, Sun Joo; Kang, Ho Jung, Synthetic Communications, 1982, vol. 12, # 9, p. 723 - 726
  作者：Kim, Sunggak、Lee, Sun Joo、Kang, Ho Jung

  DOI：——

  日期：——
• ACKERMANN, IRMTRAUD E.;BANTHORPE, DEREK V.;FORDHAM, WILLIAM D.;KINDER, JO+, LIEBIGS ANN. CHEM.,(1989) N, C. 79-81
  作者：ACKERMANN, IRMTRAUD E.、BANTHORPE, DEREK V.、FORDHAM, WILLIAM D.、KINDER, JO+

  DOI：——

  日期：——
• Development of new recyclable reagents and catalytic systems based on hypervalent iodine compounds
  作者：Mekhman S. Yusubov、Viktor V. Zhdankin

  DOI：10.1016/j.mencom.2010.06.001

  日期：2010.7

  Recent advances in the development of polymer-supported iodine(V) oxidants, recyclable monomeric hypervalent iodine(III) reagents and catalytic systems based on hypervalent iodine compounds are discussed. These efficient and environmentally friendly reagents and catalysts are particularly useful for oxidative transformations of alcohols to carbonyl compounds and for oxidations at the benzylic position.