(R)-2-(benzyloxy)-2-cyclohexylacetaldehyde | 141692-80-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-(benzyloxy)-2-cyclohexylacetaldehyde
• 英文别名: (2R)-2-cyclohexyl-2-phenylmethoxyacetaldehyde
• CAS: 141692-80-0
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: AKHOMAUEAISMTN-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-(benzyloxy)-2-cyclohexylacetaldehyde 在 氢气 、 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 生成 (4R,5R)-4-Cyclohexyl-2,2-dimethyl-5-propyl-[1,3]dioxolane
  参考文献：
  名称：

  Stereocontrolled additions of allyltri--butyl-stannane to α-hydroxyaldehyde derivatives. A useful route to monoprotected or diols.

  摘要：

  DOI：

  10.1016/s0040-4039(00)99857-5
• 作为产物：
  描述：

  (R)-(-)-六氢扁桃酸 在 氯化亚砜 、 三氟甲磺酸 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 16.5h， 生成 (R)-2-(benzyloxy)-2-cyclohexylacetaldehyde
  参考文献：
  名称：

  Stereoselective synthesis of functionalised triol units by SnCl4 promoted allylation of α-benzyloxyaldehydes: crucial role of the stoichiometry of the Lewis acid

  摘要：

  Enantiomerically pure syn-anti and syn-syn configured triol units are efficiently synthesized by the SnCl4 mediated allylation of chiral alpha-benzyloxyaldehydes with the uniquely functionalised allylstannane 9. Remarkably, the stereochemistry of the adducts is solely governed by the amount of Lewis acid employed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.084

文献信息

• Chelation controlled addition of allylstannanes to aldehydes in lithium perchlorate-diethyl ether
  作者：Kenneth J. Henry、Paul A. Grieco、Christopher T. Jagoe

  DOI：10.1016/s0040-4039(00)74150-5

  日期：1992.3

  α-Alkoxy aldehydes undergo chelation controlled addition of allylstannanes with high diastereoselectivity in the presence of 5.0 M lithium perchlorate in diethyl ether at ambient temperature and pressure.

  在环境温度和压力下，在乙醚中有5.0 M高氯酸锂存在下，α-烷氧基醛具有螯合控制的高非对映选择性的烯丙基锡烷酸加成反应。
• Chelation control associated with organometallic addition reactions in water. The high stereoselectivity offered by α- and β-hydroxyl substituents obviates the need for protecting groups
  作者：L Paquette

  DOI：10.1016/00404-0399(50)1439o-

  日期：1995.9.18

  High stereoselectivities have been observed for indium-promoted allylations of alpha- and beta-hydroxy aldehydes in aqueous media, with strong implication that chelate control can continue to operate in water.
• KO, KWANG-YOUN;FRAZEE, W. J.;ELIEL, E. L., TETRAHEDRON, 1984, 40, N 8, 1333-1343
  作者：KO, KWANG-YOUN、FRAZEE, W. J.、ELIEL, E. L.

  DOI：——

  日期：——
• Stereoselective synthesis of functionalised triol units by SnCl4 promoted allylation of α-benzyloxyaldehydes: crucial role of the stoichiometry of the Lewis acid
  作者：Christophe Dubost、Bernard Leroy、Istvan E. Markó、Bernard Tinant、Jean-Paul Declercq、Justin Bryans

  DOI：10.1016/j.tet.2004.06.084

  日期：2004.8

  Enantiomerically pure syn-anti and syn-syn configured triol units are efficiently synthesized by the SnCl4 mediated allylation of chiral alpha-benzyloxyaldehydes with the uniquely functionalised allylstannane 9. Remarkably, the stereochemistry of the adducts is solely governed by the amount of Lewis acid employed. (C) 2004 Elsevier Ltd. All rights reserved.
• Stereocontrolled additions of allyltri--butyl-stannane to α-hydroxyaldehyde derivatives. A useful route to monoprotected or diols.
  作者：Gary E. Keck、Eugene P. Boden

  DOI：10.1016/s0040-4039(00)99857-5

  日期：1984.1