(+/-)-2-[1-(methoxycarbonyl)-2-oxocyclopentyl]ethyl acetate | 54460-31-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+/-)-2-[1-(methoxycarbonyl)-2-oxocyclopentyl]ethyl acetate
• 英文别名: (+/-)-1-(2-acetoxyethyl)-2-oxocyclopentanecarboxylic acid methyl ester；2-(2-acetoxyethyl)-2-methoxy-carbonylcyclopentanone；2-(2-acetoxyethyl)-2-methoxycarbonylcyclopentanone；methyl 1-(2-acetyloxyethyl)-2-oxocyclopentane-1-carboxylate
• CAS: 54460-31-0
• 化学式: C₁₁H₁₆O₅
• 分子量: 228.245
• InChiKey: NFBRFUYNZDQFNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-2-[1-(methoxycarbonyl)-2-oxocyclopentyl]ethyl acetate 在 正丁基锂 、 二异丁基氢化铝 、 对甲苯磺酸 、 乙酰氯 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 为溶剂， 反应 51.0h， 生成 (+/-)-3a-(fluoren-9-ylidenemethyl)-2,3,4,5,3a-pentahydrocyclopenta[1,2-b]furan
  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
• 作为产物：
  描述：

  2-碘-1-乙醇乙酸酯 、 2-甲氧羰基环戊酮 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以98%的产率得到(+/-)-2-[1-(methoxycarbonyl)-2-oxocyclopentyl]ethyl acetate
  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

• 2-Oxabicyclo[3.3.0]octane compounds, process for producing the same, optical resolver, method of separating diastereomer mixture, and method of optically resolving alcohol
  申请人：Sakamoto Kei

  公开号：US20060205960A1

  公开（公告）日：2006-09-14

  2-Oxabicyclo[3.3.0]octane compounds represented by the following formula (1) (compound (1)); an optical resolver comprising at least one of the compounds (1); a process for producing the compounds (1) which comprises reacting a compound (2) or compound (3) with an alcohol (5) in the presence of an acid catalyst; a method of separating a diastereomer mixture of a compound (1); and a method of optically resolving an alcohol with the optical resolver. In the formulae, R 1 to R 10 each represents hydrogen atom, etc.; R 11 represents an alkyl group, etc.; R 12 represents a hydrocarbon group, etc.; R 13 represents a hydrocarbon group, etc.; and A represents acetyl group, etc.]

  以下是2-Oxabicyclo[3.3.0]辛烷化合物的化学式（1）（化合物（1））；包含至少一种化合物（1）的光学分离剂；制备化合物（1）的过程，包括在酸催化剂存在下将化合物（2）或化合物（3）与醇（5）反应；分离化合物（1）的对映异构体混合物的方法；以及使用光学分离剂对醇进行光学分离的方法。在化学式中，R1至R10分别表示氢原子等；R11表示烷基等；R12表示碳氢基团等；R13表示碳氢基团等；A表示乙酰基等。
• 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。
• 2-oxabicyclo[3.3.0]octane compounds, process for producing the same, optical resolver, method of separating diastereomer mixture, and method of optically resolving alcohol
  申请人：Zeon Corporation

  公开号：US07524978B2

  公开（公告）日：2009-04-28

  2-Oxabicyclo[3.3.0]octane compounds represented by the following formula (1) (compound (1)); an optical resolver comprising at least one of the compounds (1); a process for producing the compounds (1) which comprises reacting a compound (2) or compound (3) with an alcohol (5) in the presence of an acid catalyst; a method of separating a diastereomer mixture of a compound (1); and a method of optically resolving an alcohol with the optical resolver. [In the formulae, R1 to R10 each represents hydrogen atom, etc.; R11 represents an alkyl group, etc.; R12 represents a hydrocarbon group, etc.; R13 represents a hydrocarbon group, etc.; and A represents acetyl group, etc.]

  以下是2-Oxabicyclo[3.3.0]辛烷化合物的化学式（1）（化合物（1））；包括化合物（1）中至少一种的光学分离剂；制备化合物（1）的方法包括在酸催化剂的存在下将化合物（2）或化合物（3）与醇（5）反应；分离化合物（1）的对映异构体混合物的方法；以及使用光学分离剂对醇进行光学分离的方法。[在化学式中，R1至R10分别代表氢原子等；R11代表烷基等；R12代表碳氢基团等；R13代表碳氢基团等；A代表乙酰基等。]
• 2-OXABICYCLO 3.3.0 OCTANE COMPOUNDS, PROCESS FOR PRODUCING THE SAME, OPTICAL RESOLVER, METHOD OF SEPARATING DIASTEREOMER MIXTURE, AND METHOD OF OPTICALLY RESOLVING ALCOHOL
  申请人：Zeon Corporation

  公开号：EP1535917A1

  公开（公告）日：2005-06-01

  2-Oxabicyclo[3.3.0]octane compounds represented by the following formula (1) (compound (1)); an optical resolver comprising at least one of the compounds (1); a process for producing the compounds (1) which comprises reacting a compound (2) or compound (3) with an alcohol (5) in the presence of an acid catalyst; a method of separating a diastereomer mixture of a compound (1); and a method of optically resolving an alcohol with the optical resolver. [In the formulae, R1 to R10 each represents hydrogen atom, etc.; R11 represents an alkyl group, etc.; R12 represents a hydrocarbon group, etc.; R13 represents a hydrocarbon group, etc.; and A represents acetyl group, etc.]

  由下式（1）代表的 2-氧杂双环[3.3.0]辛烷化合物（化合物（1））；包含至少一种化合物（1）的光学分解剂；生产化合物（1）的工艺，该工艺包括在酸催化剂存在下使化合物（2）或化合物（3）与醇（5）反应；分离化合物（1）非对映体混合物的方法；以及用光学分解剂对醇进行光学分解的方法。 [在式中，R1 至 R10 分别代表氢原子等；R11 代表烷基等；R12 代表烃基等；R13 代表烃基等；A 代表乙酰基等。］
• OPTICAL RESOLVER, PROCESS FOR PRODUCING OPTICALLY ACTIVE ISOMER, AND 1,5-SUBSTITUTED BICYCLO (3.3.0) -2-OXAOCTANE COMPOUND
  申请人：ZEON CORPORATION

  公开号：EP1719746A1

  公开（公告）日：2006-11-08

  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 R11 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.

  一种光学分解剂，包括由式[1]、[2]或[3]表示的双环[3.3.0]-2-氧代辛烷化合物，由式[1]、[2]或[3]表示；一种生产光学活性物质的工艺，包括通过该制剂与具有活性氢原子的光学活性物质混合物反应获得非对映异构体混合物，将非对映异构体混合物解析为各非对映异构体，并通过分解非对映异构体获得(R)光学活性物质或(S)光学活性物质；以及由上式代表的化合物，其中 R11 代表芴甲基、亚芴基甲基、双（4-环己基苯基）甲基、4-（9-菲基）苯基、4-（1-芘基）苯基、4-（5-苊基）苯基或 4-（9-蒽基）苯基。使用本发明的制剂可以有效地生产出纯度极高的有用光学活性物质。