(+/-)-1-methoxy-5-formylbicyclo[3.3.0]-2-oxaoctane | 863127-04-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-1-methoxy-5-formylbicyclo[3.3.0]-2-oxaoctane
• 英文别名: (3As,6aS)-6a-methoxy-3,4,5,6-tetrahydro-2H-cyclopenta[b]furan-3a-carbaldehyde
• CAS: 863127-04-2
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: AHWXEPDZYAZSJY-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-1-methoxy-5-formylbicyclo[3.3.0]-2-oxaoctane 在 重铬酸吡啶 、 氨 、 4-甲基苯磺酸吡啶 、 lithium 、 乙酰氯 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 69.5h， 生成 (3aS,6aS)-3a-benzhydryl-6a-methoxy-3,4,5,6-tetrahydro-2H-cyclopenta[b]furan
  参考文献：
  名称：

  Highly efficient chiral resolution and determination of absolute configuration of 2-alkanols by using a cyclopenta[b]furan derivative

  摘要：

  The reaction of 3a-benzhydryi-3,3a,4,5-tetrahydro-2H-cyclopenta[hjfuran and various 2-alkanols in the presence of a catalytic amount of pyridinium 4-tolunesulfonate in dichlorornethane gave 3a-benzhydryl-6a-(1-methyl-aloxy)-hexahydrocyclopenta[b]furan in more than 90% chemical yields. The resulting diastereomeric mixture is easily separable on silica gel chromatography because of the large DeltaR(f) value (briefly 0.1). Absolute configuration of the 2-alkanols can be easily estimated by the chemical shifts of H-1 and C-13 NMR of methyne group of the benzhydryl moiety. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.104
• 作为产物：
  描述：

  (+/-)-2-[1-(methoxycarbonyl)-2-oxocyclopentyl]ethyl acetate 在 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 14.0h， 生成 (+/-)-1-methoxy-5-formylbicyclo[3.3.0]-2-oxaoctane
  参考文献：
  名称：

  一种高效合成3a位侧链各不相同的水环戊[1,2- b ]呋喃的方法

  摘要：

  （3 -a S ∗，1a R ∗）-1a-Methoxy-3a-methoxymethoxy-2,3,4,5,6,3a-hexahydrocyclopenta [1,2- b ]呋喃以2-甲氧基羰基化反应的总收率为96％制备两个步骤中的cyclopenta-1-one。该呋喃衍生物在我们最初设计的具有各种取代基的手性拆分剂的合成中用作发散中间体。在对各种合成产物进行初步评估时，发现3a-（芴-9-亚甲基）-2,3,4,5,3a-五氢环戊[1,2- b ]呋喃是一种显着改进的手性拆分剂。用于仲醇。

  DOI：

  10.1016/j.tetlet.2005.07.164

文献信息

• Agent For Optical Resolution, Process For Producing Optically Active Substance and 1,5-Substituted Bicyclo [3.3.0] -2-Oxaoctane Compound
  申请人：Nemoto Hisao

  公开号：US20080287695A1

  公开（公告）日：2008-11-20

  An agent for optical resolution comprising a bicyclo[3.3.0]-2-oxaoctane compound represented by the formula [1], [2] or [3] a process for producing an optically active substance comprising obtaining a mixture of diastereomers by reaction of the agent with a mixture of optically active substances having active hydrogen atom, resolving the mixture of diastereomers into each diastereomer and obtaining an (R) optically active substance or an (S) optically active substance by decomposition of the diastereomer; and compounds represented by the above formulae in which R 11 represents fluorenylmethyl group, fluorenylidenemethyl group, bis(4-cyclohexylphenyl)methyl group, 4-(9-phenanthryl)phenyl group, 4-(1-pyrenyl)phenyl group, 4-(5-acenaphthenyl)phenyl group or 4-(9-anthryl)phenyl group, are disclosed. A useful optically active substance having a very high purity can be produced efficiently by using the agent of the present invention.

  一种用于光学分辨的代理物，包括由公式[1]、[2]或[3]表示的二环[3.3.0]-2-氧杂辛烷化合物，以及一种生产光学活性物质的方法，包括通过将代理物与具有活性氢原子的光学活性物质混合反应，得到对映异构体混合物，将对映异构体混合物分离成每个对映异构体，并通过分解对映异构体获得(R)光学活性物质或(S)光学活性物质。本发明还揭示了由上述公式表示的化合物，其中R11代表芴甲基基团、芴亚甲基基团、双(4-环己基苯基)甲基基团、4-(9-菲)苯基基团、4-(1-芘)苯基基团、4-(5-蒽基)苯基基团或4-(9-蒽基)苯基基团。使用本发明的代理物可以高效地生产出具有非常高纯度的有用光学活性物质。
• EP1719746
  申请人：——

  公开号：——

  公开（公告）日：——
• Highly efficient chiral resolution and determination of absolute configuration of 2-alkanols by using a cyclopenta[b]furan derivative
  作者：Hisao Nemoto、Hiroe Tsutsumi、Satomi Yuzawa、Xian Peng、Weihui Zhong、Jun Xie、Norikazu Miyoshi、Ichiro Suzuki、Masayuki Shibuya

  DOI：10.1016/j.tetlet.2003.12.104

  日期：2004.2

  The reaction of 3a-benzhydryi-3,3a,4,5-tetrahydro-2H-cyclopenta[hjfuran and various 2-alkanols in the presence of a catalytic amount of pyridinium 4-tolunesulfonate in dichlorornethane gave 3a-benzhydryl-6a-(1-methyl-aloxy)-hexahydrocyclopenta[b]furan in more than 90% chemical yields. The resulting diastereomeric mixture is easily separable on silica gel chromatography because of the large DeltaR(f) value (briefly 0.1). Absolute configuration of the 2-alkanols can be easily estimated by the chemical shifts of H-1 and C-13 NMR of methyne group of the benzhydryl moiety. (C) 2003 Elsevier Ltd. All rights reserved.
• An efficient method for the synthesis of hydrocyclopenta[1,2-b]furan with various side chains at 3a-position
  作者：Weihui Zhong、Jun Xie、Xian Peng、Tomoyuki Kawamura、Hisao Nemoto

  DOI：10.1016/j.tetlet.2005.07.164

  日期：2005.10

  (3aS∗,1aR∗)-1a-Methoxy-3a-methoxycarbonyl-2,3,4,5,6,3a-hexahydrocyclopenta[1,2-b]furan was prepared in 96% overall yield from 2-methoxycarbonylated cyclopenta-1-one in two steps. This furan derivative is used as a divergent intermediate in the synthesis of our originally designed chiral resolving agents having various substitutions. During the preliminary evaluation of divergent synthetic products

  （3 -a S ∗，1a R ∗）-1a-Methoxy-3a-methoxymethoxy-2,3,4,5,6,3a-hexahydrocyclopenta [1,2- b ]呋喃以2-甲氧基羰基化反应的总收率为96％制备两个步骤中的cyclopenta-1-one。该呋喃衍生物在我们最初设计的具有各种取代基的手性拆分剂的合成中用作发散中间体。在对各种合成产物进行初步评估时，发现3a-（芴-9-亚甲基）-2,3,4,5,3a-五氢环戊[1,2- b ]呋喃是一种显着改进的手性拆分剂。用于仲醇。